From 97367734759fbde284c01bfb28cfc742615576cc Mon Sep 17 00:00:00 2001
From: Trey t <treytartt@fastmail.com>
Date: Fri, 13 Feb 2026 08:55:23 -0600
Subject: [PATCH] feat: improve planning engine travel handling, itinerary
 reordering, and scenario planners

Add TravelInfo initializers and city normalization helpers to fix repeat
city-pair disambiguation. Improve drag-and-drop reordering with segment
index tracking and source-row-aware zone calculation. Enhance all five
scenario planners with better next-day departure handling and travel
segment placement. Add comprehensive tests across all planners.

Co-Authored-By: Claude Opus 4.6 <noreply@anthropic.com>
---
 .../Core/Models/Domain/ItineraryItem.swift    |  45 ++++++
 .../Trip/Views/ItineraryReorderingLogic.swift |  20 +--
 .../Views/ItineraryTableViewController.swift  |  86 +++++++++--
 .../Views/ItineraryTableViewWrapper.swift     |  58 ++++----
 .../Features/Trip/Views/TripDetailView.swift  | 100 ++++++++-----
 .../Planning/Engine/GameDAGRouter.swift       |  41 ++---
 .../Planning/Engine/ScenarioAPlanner.swift    |  97 +++++++++---
 .../Planning/Engine/ScenarioBPlanner.swift    |  20 +++
 .../Planning/Engine/ScenarioCPlanner.swift    |  34 ++++-
 .../Planning/Engine/ScenarioDPlanner.swift    |  53 ++++++-
 .../Planning/Engine/ScenarioEPlanner.swift    | 126 ++++++++++++----
 .../Planning/Engine/TravelEstimator.swift     |   8 +-
 SportsTimeTests/Domain/TravelInfoTests.swift  |  51 +++++++
 .../Planning/GameDAGRouterTests.swift         |  30 ++++
 .../Planning/ScenarioAPlannerTests.swift      |  49 ++++++
 .../Planning/ScenarioBPlannerTests.swift      |  43 ++++++
 .../Planning/ScenarioCPlannerTests.swift      |  41 +++++
 .../Planning/ScenarioDPlannerTests.swift      |  57 +++++++
 .../Planning/ScenarioEPlannerTests.swift      | 140 ++++++++++++++++++
 19 files changed, 928 insertions(+), 171 deletions(-)
 create mode 100644 SportsTimeTests/Domain/TravelInfoTests.swift

diff --git a/SportsTime/Core/Models/Domain/ItineraryItem.swift b/SportsTime/Core/Models/Domain/ItineraryItem.swift
index 4563ff6..3394d09 100644
--- a/SportsTime/Core/Models/Domain/ItineraryItem.swift
+++ b/SportsTime/Core/Models/Domain/ItineraryItem.swift
@@ -42,6 +42,51 @@ struct TravelInfo: Codable, Hashable {
     var distanceMeters: Double?
     var durationSeconds: Double?
 
+    init(
+        fromCity: String,
+        toCity: String,
+        segmentIndex: Int? = nil,
+        distanceMeters: Double? = nil,
+        durationSeconds: Double? = nil
+    ) {
+        self.fromCity = fromCity.trimmingCharacters(in: .whitespacesAndNewlines)
+        self.toCity = toCity.trimmingCharacters(in: .whitespacesAndNewlines)
+        self.segmentIndex = segmentIndex
+        self.distanceMeters = distanceMeters
+        self.durationSeconds = durationSeconds
+    }
+
+    init(
+        segment: TravelSegment,
+        segmentIndex: Int? = nil,
+        distanceMeters: Double? = nil,
+        durationSeconds: Double? = nil
+    ) {
+        self.init(
+            fromCity: segment.fromLocation.name,
+            toCity: segment.toLocation.name,
+            segmentIndex: segmentIndex,
+            distanceMeters: distanceMeters ?? segment.distanceMeters,
+            durationSeconds: durationSeconds ?? segment.durationSeconds
+        )
+    }
+
+    static func normalizeCityName(_ city: String) -> String {
+        city.lowercased().trimmingCharacters(in: .whitespacesAndNewlines)
+    }
+
+    var normalizedFromCity: String { Self.normalizeCityName(fromCity) }
+    var normalizedToCity: String { Self.normalizeCityName(toCity) }
+
+    func matches(from: String, to: String) -> Bool {
+        normalizedFromCity == Self.normalizeCityName(from)
+            && normalizedToCity == Self.normalizeCityName(to)
+    }
+
+    func matches(segment: TravelSegment) -> Bool {
+        matches(from: segment.fromLocation.name, to: segment.toLocation.name)
+    }
+
     var formattedDistance: String {
         guard let meters = distanceMeters else { return "" }
         let miles = meters / 1609.34
diff --git a/SportsTime/Features/Trip/Views/ItineraryReorderingLogic.swift b/SportsTime/Features/Trip/Views/ItineraryReorderingLogic.swift
index 0d2c5e2..836275d 100644
--- a/SportsTime/Features/Trip/Views/ItineraryReorderingLogic.swift
+++ b/SportsTime/Features/Trip/Views/ItineraryReorderingLogic.swift
@@ -831,21 +831,23 @@ enum ItineraryReorderingLogic {
         in travelValidRanges: [String: ClosedRange<Int>],
         model: ItineraryItem? = nil
     ) -> String {
-        let suffix = "\(segment.fromLocation.name.lowercased())->\(segment.toLocation.name.lowercased())"
+        let from = TravelInfo.normalizeCityName(segment.fromLocation.name)
+        let to = TravelInfo.normalizeCityName(segment.toLocation.name)
+        let suffix = "\(from)->\(to)"
         let matchingKeys = travelValidRanges.keys.filter { $0.hasSuffix(suffix) }
 
+        if let segIdx = model?.travelInfo?.segmentIndex {
+            let indexedKey = "travel:\(segIdx):\(suffix)"
+            if matchingKeys.contains(indexedKey) {
+                return indexedKey
+            }
+            return indexedKey
+        }
+
         if matchingKeys.count == 1, let key = matchingKeys.first {
             return key
         }
 
-        // Multiple matches (repeat city pair) — use segmentIndex from model to disambiguate
-        if let segIdx = model?.travelInfo?.segmentIndex {
-            let expected = "travel:\(segIdx):\(suffix)"
-            if matchingKeys.contains(expected) {
-                return expected
-            }
-        }
-
         // Fallback: return first match or construct without index
         return matchingKeys.first ?? "travel:\(suffix)"
     }
diff --git a/SportsTime/Features/Trip/Views/ItineraryTableViewController.swift b/SportsTime/Features/Trip/Views/ItineraryTableViewController.swift
index a5e26df..22478de 100644
--- a/SportsTime/Features/Trip/Views/ItineraryTableViewController.swift
+++ b/SportsTime/Features/Trip/Views/ItineraryTableViewController.swift
@@ -321,6 +321,9 @@ final class ItineraryTableViewController: UITableViewController {
     
     /// All itinerary items (needed to build constraints)
     private var allItineraryItems: [ItineraryItem] = []
+
+    /// Canonical trip travel segment index keyed by TravelSegment UUID.
+    private var travelSegmentIndices: [UUID: Int] = [:]
     
     /// Trip day count for constraints
     private var tripDayCount: Int = 0
@@ -472,10 +475,12 @@ final class ItineraryTableViewController: UITableViewController {
     func reloadData(
         days: [ItineraryDayData],
         travelValidRanges: [String: ClosedRange<Int>],
-        itineraryItems: [ItineraryItem] = []
+        itineraryItems: [ItineraryItem] = [],
+        travelSegmentIndices: [UUID: Int] = [:]
     ) {
         self.travelValidRanges = travelValidRanges
         self.allItineraryItems = itineraryItems
+        self.travelSegmentIndices = travelSegmentIndices
         self.tripDayCount = days.count
 
         // Rebuild constraints with new data
@@ -571,12 +576,35 @@ final class ItineraryTableViewController: UITableViewController {
     /// Calculates invalid zones for a travel segment drag.
     /// Delegates to pure function and applies results to instance state.
     private func calculateTravelDragZones(segment: TravelSegment) {
+        let sourceRow = flatItems.firstIndex { item in
+            if case .travel(let rowSegment, _) = item {
+                return rowSegment.id == segment.id
+            }
+            return false
+        } ?? 0
+
         let zones = ItineraryReorderingLogic.calculateTravelDragZones(
             segment: segment,
+            sourceRow: sourceRow,
             flatItems: flatItems,
             travelValidRanges: travelValidRanges,
             constraints: constraints,
-            findTravelItem: { [weak self] segment in self?.findItineraryItem(for: segment) }
+            findTravelItem: { [weak self] segment in self?.findItineraryItem(for: segment) },
+            makeTravelItem: { [weak self] segment in
+                let segIdx = self?.travelSegmentIndices[segment.id]
+                return ItineraryItem(
+                    tripId: self?.allItineraryItems.first?.tripId ?? UUID(),
+                    day: 1,
+                    sortOrder: 0,
+                    kind: .travel(
+                        TravelInfo(
+                            segment: segment,
+                            segmentIndex: segIdx
+                        )
+                    )
+                )
+            },
+            findTravelSortOrder: { [weak self] segment in self?.findItineraryItem(for: segment)?.sortOrder }
         )
         invalidRowIndices = zones.invalidRowIndices
         validDropRows = zones.validDropRows
@@ -586,7 +614,20 @@ final class ItineraryTableViewController: UITableViewController {
     /// Calculates invalid zones for a custom item drag.
     /// Delegates to pure function and applies results to instance state.
     private func calculateCustomItemDragZones(item: ItineraryItem) {
-        let zones = ItineraryReorderingLogic.calculateCustomItemDragZones(item: item, flatItems: flatItems)
+        let sourceRow = flatItems.firstIndex { row in
+            if case .customItem(let current) = row {
+                return current.id == item.id
+            }
+            return false
+        } ?? 0
+
+        let zones = ItineraryReorderingLogic.calculateCustomItemDragZones(
+            item: item,
+            sourceRow: sourceRow,
+            flatItems: flatItems,
+            constraints: constraints,
+            findTravelSortOrder: { [weak self] segment in self?.findItineraryItem(for: segment)?.sortOrder }
+        )
         invalidRowIndices = zones.invalidRowIndices
         validDropRows = zones.validDropRows
         barrierGameIds = zones.barrierGameIds
@@ -597,23 +638,31 @@ final class ItineraryTableViewController: UITableViewController {
     /// Searches through allItineraryItems to find a matching travel item.
     /// Prefers matching by segmentIndex for disambiguation of repeat city pairs.
     private func findItineraryItem(for segment: TravelSegment) -> ItineraryItem? {
-        let fromLower = segment.fromLocation.name.lowercased()
-        let toLower = segment.toLocation.name.lowercased()
+        if let segIdx = travelSegmentIndices[segment.id] {
+            if let exact = allItineraryItems.first(where: { item in
+                guard case .travel(let info) = item.kind else { return false }
+                return info.segmentIndex == segIdx
+            }) {
+                return exact
+            }
+        }
 
         // Find all matching travel items by city pair
         let matches = allItineraryItems.filter { item in
             guard case .travel(let info) = item.kind else { return false }
-            return info.fromCity.lowercased() == fromLower
-            && info.toCity.lowercased() == toLower
+            return info.matches(segment: segment)
         }
 
         // If only one match, return it
         if matches.count <= 1 { return matches.first }
 
-        // Multiple matches (repeat city pair) — try to match by segment UUID identity
-        // The segment.id is a UUID that identifies the specific TravelSegment instance
-        // We match through the allItineraryItems which have segmentIndex set
-        return matches.first ?? nil
+        if let segIdx = travelSegmentIndices[segment.id] {
+            if let indexed = matches.first(where: { $0.travelInfo?.segmentIndex == segIdx }) {
+                return indexed
+            }
+        }
+
+        return matches.first(where: { $0.travelInfo?.segmentIndex != nil }) ?? matches.first
     }
     
     /// Applies visual feedback during drag.
@@ -767,8 +816,12 @@ final class ItineraryTableViewController: UITableViewController {
             // Travel is positioned within a day using sortOrder (can be before/after games)
             let destinationDay = dayNumber(forRow: destinationIndexPath.row)
             let sortOrder = calculateSortOrder(at: destinationIndexPath.row)
-            let segIdx = findItineraryItem(for: segment)?.travelInfo?.segmentIndex ?? 0
-            let travelId = "travel:\(segIdx):\(segment.fromLocation.name.lowercased())->\(segment.toLocation.name.lowercased())"
+            let segIdx = travelSegmentIndices[segment.id]
+                ?? findItineraryItem(for: segment)?.travelInfo?.segmentIndex
+                ?? 0
+            let from = TravelInfo.normalizeCityName(segment.fromLocation.name)
+            let to = TravelInfo.normalizeCityName(segment.toLocation.name)
+            let travelId = "travel:\(segIdx):\(from)->\(to)"
             onTravelMoved?(travelId, destinationDay, sortOrder)
             
         case .customItem(let customItem):
@@ -852,13 +905,14 @@ final class ItineraryTableViewController: UITableViewController {
             constraints: constraints,
             findTravelItem: { [weak self] segment in self?.findItineraryItem(for: segment) },
             makeTravelItem: { [weak self] segment in
-                ItineraryItem(
+                let segIdx = self?.travelSegmentIndices[segment.id]
+                return ItineraryItem(
                     tripId: self?.allItineraryItems.first?.tripId ?? UUID(),
                     day: 1,
                     sortOrder: 0,
                     kind: .travel(TravelInfo(
-                        fromCity: segment.fromLocation.name,
-                        toCity: segment.toLocation.name,
+                        segment: segment,
+                        segmentIndex: segIdx,
                         distanceMeters: segment.distanceMeters,
                         durationSeconds: segment.durationSeconds
                     ))
diff --git a/SportsTime/Features/Trip/Views/ItineraryTableViewWrapper.swift b/SportsTime/Features/Trip/Views/ItineraryTableViewWrapper.swift
index 1ea473f..d3ea918 100644
--- a/SportsTime/Features/Trip/Views/ItineraryTableViewWrapper.swift
+++ b/SportsTime/Features/Trip/Views/ItineraryTableViewWrapper.swift
@@ -82,8 +82,13 @@ struct ItineraryTableViewWrapper<HeaderContent: View>: UIViewControllerRepresent
         controller.setTableHeader(hostingController.view)
 
         // Load initial data
-        let (days, validRanges, allItemsForConstraints) = buildItineraryData()
-        controller.reloadData(days: days, travelValidRanges: validRanges, itineraryItems: allItemsForConstraints)
+        let (days, validRanges, allItemsForConstraints, travelSegmentIndices) = buildItineraryData()
+        controller.reloadData(
+            days: days,
+            travelValidRanges: validRanges,
+            itineraryItems: allItemsForConstraints,
+            travelSegmentIndices: travelSegmentIndices
+        )
 
         return controller
     }
@@ -100,15 +105,21 @@ struct ItineraryTableViewWrapper<HeaderContent: View>: UIViewControllerRepresent
         // This avoids recreating the view hierarchy and prevents infinite loops
         context.coordinator.headerHostingController?.rootView = headerContent
 
-        let (days, validRanges, allItemsForConstraints) = buildItineraryData()
-        controller.reloadData(days: days, travelValidRanges: validRanges, itineraryItems: allItemsForConstraints)
+        let (days, validRanges, allItemsForConstraints, travelSegmentIndices) = buildItineraryData()
+        controller.reloadData(
+            days: days,
+            travelValidRanges: validRanges,
+            itineraryItems: allItemsForConstraints,
+            travelSegmentIndices: travelSegmentIndices
+        )
     }
 
     // MARK: - Build Itinerary Data
 
-    private func buildItineraryData() -> ([ItineraryDayData], [String: ClosedRange<Int>], [ItineraryItem]) {
+    private func buildItineraryData() -> ([ItineraryDayData], [String: ClosedRange<Int>], [ItineraryItem], [UUID: Int]) {
         let tripDays = calculateTripDays()
         var travelValidRanges: [String: ClosedRange<Int>] = [:]
+        let travelSegmentIndices = Dictionary(uniqueKeysWithValues: trip.travelSegments.enumerated().map { ($1.id, $0) })
 
         // Build game items from RichGame data for constraint validation
         var gameItems: [ItineraryItem] = []
@@ -183,13 +194,7 @@ struct ItineraryTableViewWrapper<HeaderContent: View>: UIViewControllerRepresent
                 day: placement.day,
                 sortOrder: placement.sortOrder,
                 kind: .travel(
-                    TravelInfo(
-                        fromCity: fromCity,
-                        toCity: toCity,
-                        segmentIndex: segmentIndex,
-                        distanceMeters: segment.distanceMeters,
-                        durationSeconds: segment.durationSeconds
-                    )
+                    TravelInfo(segment: segment, segmentIndex: segmentIndex)
                 )
             )
             travelItems.append(travelItem)
@@ -218,20 +223,13 @@ struct ItineraryTableViewWrapper<HeaderContent: View>: UIViewControllerRepresent
                 .filter { $0.day == dayNum }
                 .sorted { $0.sortOrder < $1.sortOrder }
             for travel in travelsForDay {
-                // Find the segment matching this travel by segment index (preferred) or city pair (legacy)
                 if let info = travel.travelInfo {
-                    let seg: TravelSegment?
-                    if let idx = info.segmentIndex, idx < trip.travelSegments.count {
-                        seg = trip.travelSegments[idx]
-                    } else {
-                        seg = trip.travelSegments.first(where: {
-                            $0.fromLocation.name.lowercased() == info.fromCity.lowercased()
-                            && $0.toLocation.name.lowercased() == info.toCity.lowercased()
-                        })
-                    }
-                    if let seg {
-                        rows.append(.travel(seg, dayNumber: dayNum))
-                    }
+                    guard let idx = info.segmentIndex,
+                          idx >= 0,
+                          idx < trip.travelSegments.count else { continue }
+                    let seg = trip.travelSegments[idx]
+                    guard info.matches(segment: seg) else { continue }
+                    rows.append(.travel(seg, dayNumber: dayNum))
                 }
             }
             
@@ -241,7 +239,7 @@ struct ItineraryTableViewWrapper<HeaderContent: View>: UIViewControllerRepresent
                     switch r {
                     case .customItem(let it): return it.sortOrder
                     case .travel(let seg, _):
-                        let segIdx = trip.travelSegments.firstIndex(where: { $0.id == seg.id }) ?? 0
+                        let segIdx = travelSegmentIndices[seg.id] ?? 0
                         let id = stableTravelAnchorId(seg, at: segIdx)
                         return (travelOverrides[id]?.sortOrder)
                         ?? (travelItems.first(where: { ti in
@@ -265,8 +263,8 @@ struct ItineraryTableViewWrapper<HeaderContent: View>: UIViewControllerRepresent
             )
             days.append(dayData)
         }
-        
-        return (days, travelValidRanges, gameItems + itineraryItems + travelItems)
+
+        return (days, travelValidRanges, gameItems + itineraryItems + travelItems, travelSegmentIndices)
     }
     
     // MARK: - Helper Methods
@@ -294,7 +292,9 @@ struct ItineraryTableViewWrapper<HeaderContent: View>: UIViewControllerRepresent
     }
     
     private func stableTravelAnchorId(_ segment: TravelSegment, at index: Int) -> String {
-        "travel:\(index):\(segment.fromLocation.name.lowercased())->\(segment.toLocation.name.lowercased())"
+        let from = TravelInfo.normalizeCityName(segment.fromLocation.name)
+        let to = TravelInfo.normalizeCityName(segment.toLocation.name)
+        return "travel:\(index):\(from)->\(to)"
     }
     
     private func findLastGameDay(in city: String, tripDays: [Date]) -> Int {
diff --git a/SportsTime/Features/Trip/Views/TripDetailView.swift b/SportsTime/Features/Trip/Views/TripDetailView.swift
index 7f8002e..c084061 100644
--- a/SportsTime/Features/Trip/Views/TripDetailView.swift
+++ b/SportsTime/Features/Trip/Views/TripDetailView.swift
@@ -797,8 +797,8 @@ struct TripDetailView: View {
 
     /// Create a stable anchor ID for a travel segment (UUIDs regenerate on reload)
     private func stableTravelAnchorId(_ segment: TravelSegment, at index: Int) -> String {
-        let from = segment.fromLocation.name.lowercased().trimmingCharacters(in: .whitespaces)
-        let to = segment.toLocation.name.lowercased().trimmingCharacters(in: .whitespaces)
+        let from = TravelInfo.normalizeCityName(segment.fromLocation.name)
+        let to = TravelInfo.normalizeCityName(segment.toLocation.name)
         return "travel:\(index):\(from)->\(to)"
     }
 
@@ -975,6 +975,17 @@ struct TripDetailView: View {
         return index
     }
 
+    /// Canonicalize travel IDs to the current segment's normalized city pair.
+    private func canonicalTravelAnchorId(from travelId: String) -> String? {
+        guard let segmentIndex = Self.parseSegmentIndex(from: travelId),
+              segmentIndex >= 0,
+              segmentIndex < trip.travelSegments.count else {
+            return nil
+        }
+        let segment = trip.travelSegments[segmentIndex]
+        return stableTravelAnchorId(segment, at: segmentIndex)
+    }
+
     // MARK: - Map Helpers
 
     private func fetchDrivingRoutes() async {
@@ -1259,8 +1270,7 @@ struct TripDetailView: View {
                 day: day,
                 sortOrder: sortOrder,
                 kind: .travel(TravelInfo(
-                    fromCity: segment.fromLocation.name,
-                    toCity: segment.toLocation.name,
+                    segment: segment,
                     segmentIndex: segmentIndex,
                     distanceMeters: segment.distanceMeters,
                     durationSeconds: segment.durationSeconds
@@ -1387,22 +1397,32 @@ struct TripDetailView: View {
 
             for item in items where item.isTravel {
                 guard let travelInfo = item.travelInfo else { continue }
-                let from = travelInfo.fromCity.lowercased()
-                let to = travelInfo.toCity.lowercased()
-
-                if let segIdx = travelInfo.segmentIndex {
-                    // New format with segment index
-                    let travelId = "travel:\(segIdx):\(from)->\(to)"
-                    overrides[travelId] = TravelOverride(day: item.day, sortOrder: item.sortOrder)
-                } else {
-                    // Legacy record without segment index — derive index from trip segments
-                    if let segIdx = trip.travelSegments.firstIndex(where: {
-                        $0.fromLocation.name.lowercased() == from && $0.toLocation.name.lowercased() == to
-                    }) {
-                        let travelId = "travel:\(segIdx):\(from)->\(to)"
-                        overrides[travelId] = TravelOverride(day: item.day, sortOrder: item.sortOrder)
+                if let segIdx = travelInfo.segmentIndex,
+                   segIdx >= 0,
+                   segIdx < trip.travelSegments.count {
+                    let segment = trip.travelSegments[segIdx]
+                    if !travelInfo.matches(segment: segment) {
+                        print("⚠️ [TravelOverrides] Mismatched travel cities for segment \(segIdx); using canonical segment cities")
                     }
+                    let travelId = stableTravelAnchorId(segment, at: segIdx)
+                    overrides[travelId] = TravelOverride(day: item.day, sortOrder: item.sortOrder)
+                    continue
                 }
+
+                // Legacy record without segment index: only accept if the city pair maps uniquely.
+                let matches = trip.travelSegments.enumerated().filter { _, segment in
+                    travelInfo.matches(segment: segment)
+                }
+
+                guard matches.count == 1, let match = matches.first else {
+                    print("⚠️ [TravelOverrides] Ignoring ambiguous legacy travel override \(travelInfo.fromCity)->\(travelInfo.toCity)")
+                    continue
+                }
+
+                let segIdx = match.offset
+                let segment = match.element
+                let travelId = stableTravelAnchorId(segment, at: segIdx)
+                overrides[travelId] = TravelOverride(day: item.day, sortOrder: item.sortOrder)
             }
 
             travelOverrides = overrides
@@ -1478,8 +1498,11 @@ struct TripDetailView: View {
                 Task { @MainActor in
                     // Check if this is a travel segment being dropped
                     if droppedId.hasPrefix("travel:") {
+                        guard let canonicalTravelId = self.canonicalTravelAnchorId(from: droppedId) else {
+                            return
+                        }
                         // Validate travel is within valid bounds (day-level)
-                        if let validRange = self.validDayRange(for: droppedId) {
+                        if let validRange = self.validDayRange(for: canonicalTravelId) {
                             guard validRange.contains(dayNumber) else {
                                 return
                             }
@@ -1499,12 +1522,12 @@ struct TripDetailView: View {
                         let newSortOrder = max(maxSortOrderOnDay + 1.0, 1.0)
                         
                         withAnimation {
-                            self.travelOverrides[droppedId] = TravelOverride(day: dayNumber, sortOrder: newSortOrder)
+                            self.travelOverrides[canonicalTravelId] = TravelOverride(day: dayNumber, sortOrder: newSortOrder)
                         }
                         
                         // Persist to CloudKit as a travel ItineraryItem
                         await self.saveTravelDayOverride(
-                            travelAnchorId: droppedId,
+                            travelAnchorId: canonicalTravelId,
                             displayDay: dayNumber,
                             sortOrder: newSortOrder
                         )
@@ -1531,46 +1554,40 @@ struct TripDetailView: View {
     private func saveTravelDayOverride(travelAnchorId: String, displayDay: Int, sortOrder: Double) async {
         print("💾 [TravelOverrides] Saving override: \(travelAnchorId) -> day \(displayDay), sortOrder \(sortOrder)")
 
-        // Parse travel ID (format: "travel:INDEX:from->to")
-        let segmentIndex = Self.parseSegmentIndex(from: travelAnchorId)
-        let stripped = travelAnchorId.replacingOccurrences(of: "travel:", with: "")
-        let colonParts = stripped.components(separatedBy: ":")
-        // After removing "travel:", format is "INDEX:from->to"
-        let cityPart = colonParts.count >= 2 ? colonParts.dropFirst().joined(separator: ":") : stripped
-        let cityParts = cityPart.components(separatedBy: "->")
-        guard cityParts.count == 2 else {
-            print("❌ [TravelOverrides] Invalid travel ID format: \(travelAnchorId)")
+        guard let segmentIndex = Self.parseSegmentIndex(from: travelAnchorId),
+              segmentIndex >= 0,
+              segmentIndex < trip.travelSegments.count else {
+            print("❌ [TravelOverrides] Invalid travel segment index in ID: \(travelAnchorId)")
             return
         }
 
-        let fromCity = cityParts[0]
-        let toCity = cityParts[1]
+        let segment = trip.travelSegments[segmentIndex]
+        let canonicalTravelId = stableTravelAnchorId(segment, at: segmentIndex)
+        let canonicalInfo = TravelInfo(segment: segment, segmentIndex: segmentIndex)
 
-        // Find existing travel item matching by segment index (preferred) or city pair (legacy)
+        // Find existing travel item matching by segment index (preferred) or city pair (legacy fallback).
         if let existingIndex = itineraryItems.firstIndex(where: {
             guard $0.isTravel, let info = $0.travelInfo else { return false }
-            // Match by segment index if available
-            if let idx = segmentIndex, let itemIdx = info.segmentIndex {
-                return idx == itemIdx
+            if let itemIdx = info.segmentIndex {
+                return itemIdx == segmentIndex
             }
-            // Legacy fallback: match by city pair
-            return info.fromCity.lowercased() == fromCity && info.toCity.lowercased() == toCity
+            return info.matches(segment: segment)
         }) {
             // Update existing
             var updated = itineraryItems[existingIndex]
             updated.day = displayDay
             updated.sortOrder = sortOrder
             updated.modifiedAt = Date()
+            updated.kind = .travel(canonicalInfo)
             itineraryItems[existingIndex] = updated
             await ItineraryItemService.shared.updateItem(updated)
         } else {
             // Create new travel item
-            let travelInfo = TravelInfo(fromCity: fromCity, toCity: toCity, segmentIndex: segmentIndex)
             let item = ItineraryItem(
                 tripId: trip.id,
                 day: displayDay,
                 sortOrder: sortOrder,
-                kind: .travel(travelInfo)
+                kind: .travel(canonicalInfo)
             )
             itineraryItems.append(item)
             do {
@@ -1580,6 +1597,9 @@ struct TripDetailView: View {
                 return
             }
         }
+        if canonicalTravelId != travelAnchorId {
+            print("ℹ️ [TravelOverrides] Canonicalized travel ID to \(canonicalTravelId)")
+        }
         print("✅ [TravelOverrides] Saved to CloudKit")
     }
 }
diff --git a/SportsTime/Planning/Engine/GameDAGRouter.swift b/SportsTime/Planning/Engine/GameDAGRouter.swift
index 453bc1c..3a8fc12 100644
--- a/SportsTime/Planning/Engine/GameDAGRouter.swift
+++ b/SportsTime/Planning/Engine/GameDAGRouter.swift
@@ -71,9 +71,6 @@ enum GameDAGRouter {
     /// Buffer time after game ends before we can depart (hours)
     private static let gameEndBufferHours: Double = 3.0
 
-    /// Maximum days ahead to consider for next game (1 = next day only, 5 = allows multi-day drives)
-    private static let maxDayLookahead = 5
-
     // MARK: - Route Profile
 
     /// Captures the key metrics of a route for diversity analysis
@@ -176,14 +173,29 @@ enum GameDAGRouter {
         // Step 2.5: Calculate effective beam width for this dataset size
         let scaledBeamWidth = effectiveBeamWidth(gameCount: games.count, requestedWidth: beamWidth)
 
-        // Step 3: Initialize beam with first few days' games as starting points
-        var beam: [[Game]] = []
-        for dayIndex in sortedDays.prefix(maxDayLookahead) {
-            if let dayGames = buckets[dayIndex] {
-                for game in dayGames {
-                    beam.append([game])
-                }
-            }
+        // Step 3: Initialize beam from all games so later-starting valid routes
+        // (including anchor-driven routes) are not dropped up front.
+        let initialBeam = sortedGames.map { [$0] }
+        let beamSeedLimit = max(scaledBeamWidth * 2, 50)
+
+        let anchorSeeds = initialBeam.filter { path in
+            guard let game = path.first else { return false }
+            return anchorGameIds.contains(game.id)
+        }
+        let nonAnchorSeeds = initialBeam.filter { path in
+            guard let game = path.first else { return false }
+            return !anchorGameIds.contains(game.id)
+        }
+
+        let reservedForAnchors = min(anchorSeeds.count, beamSeedLimit)
+        let remainingSlots = max(0, beamSeedLimit - reservedForAnchors)
+        let prunedNonAnchorSeeds = remainingSlots > 0
+            ? diversityPrune(nonAnchorSeeds, stadiums: stadiums, targetCount: remainingSlots)
+            : []
+
+        var beam = Array(anchorSeeds.prefix(reservedForAnchors)) + prunedNonAnchorSeeds
+        if beam.isEmpty {
+            beam = diversityPrune(initialBeam, stadiums: stadiums, targetCount: beamSeedLimit)
         }
 
         // Step 4: Expand beam day by day with early termination
@@ -200,13 +212,6 @@ enum GameDAGRouter {
 
             for path in beam {
                 guard let lastGame = path.last else { continue }
-                let lastGameDay = dayIndexFor(lastGame.startTime, referenceDate: sortedGames[0].startTime)
-
-                // Skip if this day is too far ahead for this route
-                if dayIndex > lastGameDay + maxDayLookahead {
-                    nextBeam.append(path)
-                    continue
-                }
 
                 // Try adding each of today's games
                 for candidate in todaysGames {
diff --git a/SportsTime/Planning/Engine/ScenarioAPlanner.swift b/SportsTime/Planning/Engine/ScenarioAPlanner.swift
index 4225009..2112994 100644
--- a/SportsTime/Planning/Engine/ScenarioAPlanner.swift
+++ b/SportsTime/Planning/Engine/ScenarioAPlanner.swift
@@ -15,7 +15,7 @@ import CoreLocation
 ///
 /// Input:
 ///   - date_range: Required. The trip dates (e.g., Jan 5-15)
-///   - must_stop: Optional. A location they must visit (filters to home games in that city)
+///   - must_stop: Optional. One or more locations the route must include
 ///
 /// Output:
 ///   - Success: Ranked list of itinerary options
@@ -30,8 +30,8 @@ import CoreLocation
 ///   - No date range → returns .failure with .missingDateRange
 ///   - No games in date range → returns .failure with .noGamesInRange
 ///   - With selectedRegions → only includes games in those regions
-///   - With mustStopLocation → filters to home games in that city
-///   - Empty games after must-stop filter → .failure with .noGamesInRange
+///   - With mustStopLocations → route must include at least one game in each must-stop city
+///   - Missing games for any must-stop city → .failure with .noGamesInRange
 ///   - No valid routes from GameDAGRouter → .failure with .noValidRoutes
 ///   - All routes fail ItineraryBuilder → .failure with .constraintsUnsatisfiable
 ///   - Success → returns sorted itineraries based on leisureLevel
@@ -109,33 +109,36 @@ final class ScenarioAPlanner: ScenarioPlanner {
         // ──────────────────────────────────────────────────────────────────
         // Step 2b: Filter by must-stop locations (if any)
         // ──────────────────────────────────────────────────────────────────
-        // If user specified a must-stop city, filter to HOME games in that city.
-        // A "home game" means the stadium is in the must-stop city.
-        var filteredGames = gamesInRange
-        if let mustStop = request.mustStopLocation {
-            let mustStopCity = mustStop.name.lowercased()
-            filteredGames = gamesInRange.filter { game in
-                guard let stadium = request.stadiums[game.stadiumId] else { return false }
-                let stadiumCity = stadium.city.lowercased()
-                // Match if either contains the other (handles "Chicago" vs "Chicago, IL")
-                return stadiumCity.contains(mustStopCity) || mustStopCity.contains(stadiumCity)
+        // Must-stops are route constraints, not exclusive filters.
+        // Keep all games in range, then require routes to include each must-stop city.
+        let requiredMustStops = request.preferences.mustStopLocations.filter { stop in
+            !normalizeCityName(stop.name).isEmpty
+        }
+
+        if !requiredMustStops.isEmpty {
+            let missingMustStops = requiredMustStops.filter { mustStop in
+                !gamesInRange.contains { game in
+                    gameMatchesCity(game, cityName: mustStop.name, stadiums: request.stadiums)
+                }
             }
 
-            if filteredGames.isEmpty {
+            if !missingMustStops.isEmpty {
+                let violations = missingMustStops.map { missing in
+                    ConstraintViolation(
+                        type: .mustStop,
+                        description: "No home games found in \(missing.name) during selected dates",
+                        severity: .error
+                    )
+                }
                 return .failure(
                     PlanningFailure(
                         reason: .noGamesInRange,
-                        violations: [
-                            ConstraintViolation(
-                                type: .mustStop,
-                                description: "No home games found in \(mustStop.name) during selected dates",
-                                severity: .error
-                            )
-                        ]
+                        violations: violations
                     )
                 )
             }
         }
+        let filteredGames = gamesInRange
 
         // ──────────────────────────────────────────────────────────────────
         // Step 3: Find ALL geographically sensible route variations
@@ -177,6 +180,18 @@ final class ScenarioAPlanner: ScenarioPlanner {
         // Deduplicate routes (same game IDs)
         validRoutes = deduplicateRoutes(validRoutes)
 
+        // Enforce must-stop coverage after route generation so non-must-stop games can
+        // still be included as connective "bonus" cities.
+        if !requiredMustStops.isEmpty {
+            validRoutes = validRoutes.filter { route in
+                routeSatisfiesMustStops(
+                    route,
+                    mustStops: requiredMustStops,
+                    stadiums: request.stadiums
+                )
+            }
+        }
+
         print("🔍 ScenarioA: filteredGames=\(filteredGames.count), validRoutes=\(validRoutes.count)")
         if let firstRoute = validRoutes.first {
             print("🔍 ScenarioA: First route has \(firstRoute.count) games")
@@ -185,13 +200,16 @@ final class ScenarioAPlanner: ScenarioPlanner {
         }
 
         if validRoutes.isEmpty {
+            let noMustStopSatisfyingRoutes = !requiredMustStops.isEmpty
             return .failure(
                 PlanningFailure(
                     reason: .noValidRoutes,
                     violations: [
                         ConstraintViolation(
-                            type: .geographicSanity,
-                            description: "No geographically sensible route found for games in this date range",
+                            type: noMustStopSatisfyingRoutes ? .mustStop : .geographicSanity,
+                            description: noMustStopSatisfyingRoutes
+                                ? "No valid route can include all required must-stop cities"
+                                : "No geographically sensible route found for games in this date range",
                             severity: .error
                         )
                     ]
@@ -406,6 +424,39 @@ final class ScenarioAPlanner: ScenarioPlanner {
         return unique
     }
 
+    private func routeSatisfiesMustStops(
+        _ route: [Game],
+        mustStops: [LocationInput],
+        stadiums: [String: Stadium]
+    ) -> Bool {
+        mustStops.allSatisfy { mustStop in
+            route.contains { game in
+                gameMatchesCity(game, cityName: mustStop.name, stadiums: stadiums)
+            }
+        }
+    }
+
+    private func gameMatchesCity(
+        _ game: Game,
+        cityName: String,
+        stadiums: [String: Stadium]
+    ) -> Bool {
+        guard let stadium = stadiums[game.stadiumId] else { return false }
+        let targetCity = normalizeCityName(cityName)
+        let stadiumCity = normalizeCityName(stadium.city)
+        guard !targetCity.isEmpty, !stadiumCity.isEmpty else { return false }
+        return stadiumCity == targetCity || stadiumCity.contains(targetCity) || targetCity.contains(stadiumCity)
+    }
+
+    private func normalizeCityName(_ value: String) -> String {
+        let cityPart = value.split(separator: ",", maxSplits: 1).first.map(String.init) ?? value
+        return cityPart
+            .lowercased()
+            .replacingOccurrences(of: ".", with: "")
+            .split(whereSeparator: \.isWhitespace)
+            .joined(separator: " ")
+    }
+
     // MARK: - Regional Route Finding
 
     /// Finds routes by running beam search separately for each geographic region.
diff --git a/SportsTime/Planning/Engine/ScenarioBPlanner.swift b/SportsTime/Planning/Engine/ScenarioBPlanner.swift
index 097e957..559f7bc 100644
--- a/SportsTime/Planning/Engine/ScenarioBPlanner.swift
+++ b/SportsTime/Planning/Engine/ScenarioBPlanner.swift
@@ -75,6 +75,26 @@ final class ScenarioBPlanner: ScenarioPlanner {
             )
         }
 
+        // In explicit date-range mode, fail fast if selected anchors are out of range.
+        let isGameFirstMode = request.preferences.planningMode == .gameFirst
+        if !isGameFirstMode, let explicitRange = request.dateRange {
+            let outOfRangeAnchors = selectedGames.filter { !explicitRange.contains($0.startTime) }
+            if !outOfRangeAnchors.isEmpty {
+                return .failure(
+                    PlanningFailure(
+                        reason: .dateRangeViolation(games: outOfRangeAnchors),
+                        violations: [
+                            ConstraintViolation(
+                                type: .dateRange,
+                                description: "\(outOfRangeAnchors.count) selected game(s) are outside the requested date range",
+                                severity: .error
+                            )
+                        ]
+                    )
+                )
+            }
+        }
+
         // ──────────────────────────────────────────────────────────────────
         // Step 2: Generate date ranges (sliding window or single range)
         // ──────────────────────────────────────────────────────────────────
diff --git a/SportsTime/Planning/Engine/ScenarioCPlanner.swift b/SportsTime/Planning/Engine/ScenarioCPlanner.swift
index 1d39401..4ac48f8 100644
--- a/SportsTime/Planning/Engine/ScenarioCPlanner.swift
+++ b/SportsTime/Planning/Engine/ScenarioCPlanner.swift
@@ -295,12 +295,42 @@ final class ScenarioCPlanner: ScenarioPlanner {
         cityName: String,
         stadiums: [String: Stadium]
     ) -> [Stadium] {
-        let normalizedCity = cityName.lowercased().trimmingCharacters(in: .whitespaces)
+        let normalizedCity = normalizeCityName(cityName)
         return stadiums.values.filter { stadium in
-            stadium.city.lowercased().trimmingCharacters(in: .whitespaces) == normalizedCity
+            let normalizedStadiumCity = normalizeCityName(stadium.city)
+            if normalizedStadiumCity == normalizedCity { return true }
+            return normalizedStadiumCity.contains(normalizedCity) || normalizedCity.contains(normalizedStadiumCity)
         }
     }
 
+    /// Normalizes city labels for resilient user-input matching.
+    private func normalizeCityName(_ raw: String) -> String {
+        // Keep the city component before state suffixes like "City, ST".
+        let cityPart = raw.split(separator: ",", maxSplits: 1).first.map(String.init) ?? raw
+        var normalized = cityPart
+            .lowercased()
+            .replacingOccurrences(of: ".", with: "")
+            .trimmingCharacters(in: .whitespacesAndNewlines)
+
+        let aliases: [String: String] = [
+            "nyc": "new york",
+            "new york city": "new york",
+            "la": "los angeles",
+            "sf": "san francisco",
+            "dc": "washington",
+            "washington dc": "washington"
+        ]
+
+        if let aliased = aliases[normalized] {
+            normalized = aliased
+        }
+
+        // Collapse repeated spaces after punctuation/alias normalization.
+        return normalized
+            .split(whereSeparator: \.isWhitespace)
+            .joined(separator: " ")
+    }
+
     /// Finds stadiums that make forward progress from start to end.
     ///
     /// A stadium is "directional" if visiting it doesn't significantly increase
diff --git a/SportsTime/Planning/Engine/ScenarioDPlanner.swift b/SportsTime/Planning/Engine/ScenarioDPlanner.swift
index e0505eb..f9fae80 100644
--- a/SportsTime/Planning/Engine/ScenarioDPlanner.swift
+++ b/SportsTime/Planning/Engine/ScenarioDPlanner.swift
@@ -18,7 +18,7 @@ import CoreLocation
 ///   - date_range: Required. The trip dates.
 ///   - selectedRegions: Optional. Filter to specific regions.
 ///   - useHomeLocation: Whether to start/end from user's home.
-///   - startLocation: Required if useHomeLocation is true.
+///   - startLocation: Used as start/end home stop when provided.
 ///
 /// Output:
 ///   - Success: Ranked list of itinerary options
@@ -173,6 +173,11 @@ final class ScenarioDPlanner: ScenarioPlanner {
         // ──────────────────────────────────────────────────────────────────
         // Step 5: Prepare for routing
         // ──────────────────────────────────────────────────────────────────
+        let homeLocation: LocationInput? = {
+            guard request.preferences.useHomeLocation else { return nil }
+            return request.startLocation
+        }()
+
         // NOTE: We do NOT filter by repeat city here. The GameDAGRouter handles
         // allowRepeatCities internally, which allows it to pick the optimal game
         // per city for route feasibility (e.g., pick July 29 Anaheim instead of
@@ -232,10 +237,13 @@ final class ScenarioDPlanner: ScenarioPlanner {
 
         for (index, routeGames) in validRoutes.enumerated() {
             // Build stops for this route
-            let stops = buildStops(from: routeGames, stadiums: request.stadiums)
-
+            var stops = buildStops(from: routeGames, stadiums: request.stadiums)
             guard !stops.isEmpty else { continue }
 
+            if let homeLocation {
+                stops = buildStopsWithHomeEndpoints(home: homeLocation, gameStops: stops)
+            }
+
             // Calculate travel segments using shared ItineraryBuilder
             guard let itinerary = ItineraryBuilder.build(
                 stops: stops,
@@ -401,6 +409,45 @@ final class ScenarioDPlanner: ScenarioPlanner {
         )
     }
 
+    /// Wraps game stops with optional home start/end waypoints.
+    private func buildStopsWithHomeEndpoints(
+        home: LocationInput,
+        gameStops: [ItineraryStop]
+    ) -> [ItineraryStop] {
+        guard !gameStops.isEmpty else { return [] }
+
+        let calendar = Calendar.current
+        let firstGameDay = gameStops.first?.arrivalDate ?? Date()
+        let startDay = calendar.date(byAdding: .day, value: -1, to: firstGameDay) ?? firstGameDay
+
+        let startStop = ItineraryStop(
+            city: home.name,
+            state: "",
+            coordinate: home.coordinate,
+            games: [],
+            arrivalDate: startDay,
+            departureDate: startDay,
+            location: home,
+            firstGameStart: nil
+        )
+
+        let lastGameDay = gameStops.last?.departureDate ?? firstGameDay
+        let endDay = calendar.date(byAdding: .day, value: 1, to: lastGameDay) ?? lastGameDay
+
+        let endStop = ItineraryStop(
+            city: home.name,
+            state: "",
+            coordinate: home.coordinate,
+            games: [],
+            arrivalDate: endDay,
+            departureDate: endDay,
+            location: home,
+            firstGameStart: nil
+        )
+
+        return [startStop] + gameStops + [endStop]
+    }
+
     // MARK: - Route Deduplication
 
     /// Removes duplicate routes (routes with identical game IDs).
diff --git a/SportsTime/Planning/Engine/ScenarioEPlanner.swift b/SportsTime/Planning/Engine/ScenarioEPlanner.swift
index 897fcba..d4ef39e 100644
--- a/SportsTime/Planning/Engine/ScenarioEPlanner.swift
+++ b/SportsTime/Planning/Engine/ScenarioEPlanner.swift
@@ -16,7 +16,7 @@
 //  2. Generate all N-day windows (N = selectedTeamIds.count * 2)
 //  3. Filter to windows where each selected team has at least 1 home game
 //  4. Cap at 50 windows (sample if more exist)
-//  5. For each valid window, find routes using GameDAGRouter with team games as anchors
+//  5. For each valid window, find routes using anchor strategies + fallback search
 //  6. Rank by shortest duration + minimal miles
 //  7. Return top 10 results
 //
@@ -168,9 +168,8 @@ final class ScenarioEPlanner: ScenarioPlanner {
 
         for (windowIndex, window) in windowsToEvaluate.enumerated() {
             // Collect games in this window
-            // Use one home game per team as anchors (the best one for route efficiency)
-            var gamesInWindow: [Game] = []
-            var anchorGameIds = Set<String>()
+            var gamesByTeamInWindow: [String: [Game]] = [:]
+            var hasAllTeamsInWindow = true
 
             for teamId in selectedTeamIds {
                 guard let teamGames = homeGamesByTeam[teamId] else { continue }
@@ -181,32 +180,68 @@ final class ScenarioEPlanner: ScenarioPlanner {
                 if teamGamesInWindow.isEmpty {
                     // Window doesn't have a game for this team - skip this window
                     // This shouldn't happen since we pre-filtered windows
-                    continue
+                    hasAllTeamsInWindow = false
+                    break
                 }
 
-                // Add all games to the pool
-                gamesInWindow.append(contentsOf: teamGamesInWindow)
-
-                // Mark the earliest game as anchor (must visit this team)
-                if let earliestGame = teamGamesInWindow.sorted(by: { $0.startTime < $1.startTime }).first {
-                    anchorGameIds.insert(earliestGame.id)
-                }
+                gamesByTeamInWindow[teamId] = teamGamesInWindow
             }
 
-            // Skip if we don't have anchors for all teams
-            guard anchorGameIds.count == selectedTeamIds.count else { continue }
+            guard hasAllTeamsInWindow else { continue }
 
             // Remove duplicate games (same game could be added multiple times if team plays multiple home games)
+            let gamesInWindow = gamesByTeamInWindow.values.flatMap { $0 }
             let uniqueGames = Array(Set(gamesInWindow)).sorted { $0.startTime < $1.startTime }
+            guard !uniqueGames.isEmpty else { continue }
 
-            // Find routes using GameDAGRouter with anchor games
-            let validRoutes = GameDAGRouter.findAllSensibleRoutes(
+            // Primary pass: earliest anchor set for each team.
+            let earliestAnchorIds = Set(gamesByTeamInWindow.values.compactMap { games in
+                games.min(by: { $0.startTime < $1.startTime })?.id
+            })
+
+            var candidateRoutes = GameDAGRouter.findAllSensibleRoutes(
                 from: uniqueGames,
                 stadiums: request.stadiums,
-                anchorGameIds: anchorGameIds,
+                anchorGameIds: earliestAnchorIds,
                 allowRepeatCities: request.preferences.allowRepeatCities,
                 stopBuilder: buildStops
             )
+            var validRoutes = candidateRoutes.filter { route in
+                routeCoversAllSelectedTeams(route, selectedTeamIds: selectedTeamIds)
+            }
+
+            // Fallback pass: avoid over-constraining to earliest anchors.
+            if validRoutes.isEmpty {
+                let latestAnchorIds = Set(gamesByTeamInWindow.values.compactMap { games in
+                    games.max(by: { $0.startTime < $1.startTime })?.id
+                })
+
+                if latestAnchorIds != earliestAnchorIds {
+                    let latestAnchorRoutes = GameDAGRouter.findAllSensibleRoutes(
+                        from: uniqueGames,
+                        stadiums: request.stadiums,
+                        anchorGameIds: latestAnchorIds,
+                        allowRepeatCities: request.preferences.allowRepeatCities,
+                        stopBuilder: buildStops
+                    )
+                    candidateRoutes.append(contentsOf: latestAnchorRoutes)
+                }
+
+                let noAnchorRoutes = GameDAGRouter.findAllSensibleRoutes(
+                    from: uniqueGames,
+                    stadiums: request.stadiums,
+                    allowRepeatCities: request.preferences.allowRepeatCities,
+                    stopBuilder: buildStops
+                )
+                candidateRoutes.append(contentsOf: noAnchorRoutes)
+
+                candidateRoutes = deduplicateRoutes(candidateRoutes)
+                validRoutes = candidateRoutes.filter { route in
+                    routeCoversAllSelectedTeams(route, selectedTeamIds: selectedTeamIds)
+                }
+            }
+
+            validRoutes = deduplicateRoutes(validRoutes)
 
             // Build itineraries for valid routes
             for routeGames in validRoutes {
@@ -228,12 +263,7 @@ final class ScenarioEPlanner: ScenarioPlanner {
                 dateFormatter.dateFormat = "MMM d"
                 let windowDesc = "\(dateFormatter.string(from: window.start)) - \(dateFormatter.string(from: window.end))"
 
-                let teamsVisited = routeGames.compactMap { game -> String? in
-                    if anchorGameIds.contains(game.id) {
-                        return request.teams[game.homeTeamId]?.abbreviation ?? game.homeTeamId
-                    }
-                    return nil
-                }.joined(separator: ", ")
+                let teamsVisited = orderedTeamLabels(for: routeGames, teams: request.teams)
 
                 let cities = stops.map { $0.city }.joined(separator: " -> ")
 
@@ -273,7 +303,7 @@ final class ScenarioEPlanner: ScenarioPlanner {
             )
         }
 
-        // Deduplicate options (same stops in same order)
+        // Deduplicate options (same stop-day-game structure)
         let uniqueOptions = deduplicateOptions(allItineraryOptions)
 
         // Sort by: shortest duration first, then fewest miles
@@ -460,14 +490,19 @@ final class ScenarioEPlanner: ScenarioPlanner {
 
     // MARK: - Deduplication
 
-    /// Removes duplicate itinerary options (same stops in same order).
+    /// Removes duplicate itinerary options (same stop-day-game structure).
     private func deduplicateOptions(_ options: [ItineraryOption]) -> [ItineraryOption] {
         var seen = Set<String>()
         var unique: [ItineraryOption] = []
+        let calendar = Calendar.current
 
         for option in options {
-            // Create key from stop cities in order
-            let key = option.stops.map { $0.city }.joined(separator: "-")
+            // Key by stop city + day + game IDs to avoid collapsing distinct itineraries.
+            let key = option.stops.map { stop in
+                let day = Int(calendar.startOfDay(for: stop.arrivalDate).timeIntervalSince1970)
+                let gameKey = stop.games.sorted().joined(separator: ",")
+                return "\(stop.city)|\(day)|\(gameKey)"
+            }.joined(separator: "->")
             if !seen.contains(key) {
                 seen.insert(key)
                 unique.append(option)
@@ -477,6 +512,43 @@ final class ScenarioEPlanner: ScenarioPlanner {
         return unique
     }
 
+    /// Removes duplicate game routes (same game IDs in any order).
+    private func deduplicateRoutes(_ routes: [[Game]]) -> [[Game]] {
+        var seen = Set<String>()
+        var unique: [[Game]] = []
+
+        for route in routes {
+            let key = route.map { $0.id }.sorted().joined(separator: "-")
+            if !seen.contains(key) {
+                seen.insert(key)
+                unique.append(route)
+            }
+        }
+
+        return unique
+    }
+
+    /// Returns true if a route includes at least one home game for each selected team.
+    private func routeCoversAllSelectedTeams(_ route: [Game], selectedTeamIds: Set<String>) -> Bool {
+        let homeTeamsInRoute = Set(route.map { $0.homeTeamId })
+        return selectedTeamIds.isSubset(of: homeTeamsInRoute)
+    }
+
+    /// Team labels in first-visit order for itinerary rationale text.
+    private func orderedTeamLabels(for route: [Game], teams: [String: Team]) -> String {
+        var seen = Set<String>()
+        var labels: [String] = []
+
+        for game in route {
+            let teamId = game.homeTeamId
+            guard !seen.contains(teamId) else { continue }
+            seen.insert(teamId)
+            labels.append(teams[teamId]?.abbreviation ?? teamId)
+        }
+
+        return labels.joined(separator: ", ")
+    }
+
     // MARK: - Trip Duration Calculation
 
     /// Calculates trip duration in days for an itinerary option.
diff --git a/SportsTime/Planning/Engine/TravelEstimator.swift b/SportsTime/Planning/Engine/TravelEstimator.swift
index 72d5b90..fae5839 100644
--- a/SportsTime/Planning/Engine/TravelEstimator.swift
+++ b/SportsTime/Planning/Engine/TravelEstimator.swift
@@ -58,8 +58,8 @@ enum TravelEstimator {
         let distanceMiles = calculateDistanceMiles(from: from, to: to)
         let drivingHours = distanceMiles / averageSpeedMph
 
-        // Maximum allowed: 5 days of driving (matches GameDAGRouter.maxDayLookahead)
-        // This allows multi-day cross-country segments like Chicago → Anaheim
+        // Maximum allowed: 5 days of driving as a conservative hard cap.
+        // This allows multi-day cross-country segments like Chicago → Anaheim.
         let maxAllowedHours = constraints.maxDailyDrivingHours * 5.0
         if drivingHours > maxAllowedHours {
             return nil
@@ -103,8 +103,8 @@ enum TravelEstimator {
         let distanceMiles = distanceMeters * 0.000621371 * roadRoutingFactor
         let drivingHours = distanceMiles / averageSpeedMph
 
-        // Maximum allowed: 5 days of driving (matches GameDAGRouter.maxDayLookahead)
-        // This allows multi-day cross-country segments like Chicago → Anaheim
+        // Maximum allowed: 5 days of driving as a conservative hard cap.
+        // This allows multi-day cross-country segments like Chicago → Anaheim.
         let maxAllowedHours = constraints.maxDailyDrivingHours * 5.0
         if drivingHours > maxAllowedHours {
             return nil
diff --git a/SportsTimeTests/Domain/TravelInfoTests.swift b/SportsTimeTests/Domain/TravelInfoTests.swift
new file mode 100644
index 0000000..dd5881e
--- /dev/null
+++ b/SportsTimeTests/Domain/TravelInfoTests.swift
@@ -0,0 +1,51 @@
+//
+//  TravelInfoTests.swift
+//  SportsTimeTests
+//
+//  Tests for canonical TravelInfo construction and city matching.
+//
+
+import Testing
+@testable import SportsTime
+
+@Suite("TravelInfo")
+struct TravelInfoTests {
+
+    private func makeSegment(from: String, to: String) -> TravelSegment {
+        TravelSegment(
+            fromLocation: LocationInput(name: from),
+            toLocation: LocationInput(name: to),
+            travelMode: .drive,
+            distanceMeters: 120_000,
+            durationSeconds: 7_200
+        )
+    }
+
+    @Test("init(segment:) derives canonical city pair and metrics")
+    func initFromSegment() {
+        let segment = makeSegment(from: "Detroit", to: "Chicago")
+        let info = TravelInfo(segment: segment, segmentIndex: 2)
+
+        #expect(info.fromCity == "Detroit")
+        #expect(info.toCity == "Chicago")
+        #expect(info.segmentIndex == 2)
+        #expect(info.distanceMeters == segment.distanceMeters)
+        #expect(info.durationSeconds == segment.durationSeconds)
+    }
+
+    @Test("normalizeCityName trims and lowercases")
+    func normalizeCityName() {
+        #expect(TravelInfo.normalizeCityName("  New York  ") == "new york")
+    }
+
+    @Test("matches(segment:) uses normalized city comparison")
+    func matchesSegment() {
+        let segment = makeSegment(from: "Seattle", to: "Portland")
+        let info = TravelInfo(fromCity: "  seattle ", toCity: "PORTLAND  ")
+
+        #expect(info.matches(segment: segment))
+        #expect(info.matches(from: "SEATTLE", to: "portland"))
+        #expect(!info.matches(from: "Seattle", to: "San Francisco"))
+    }
+}
+
diff --git a/SportsTimeTests/Planning/GameDAGRouterTests.swift b/SportsTimeTests/Planning/GameDAGRouterTests.swift
index d328c89..3ac35c9 100644
--- a/SportsTimeTests/Planning/GameDAGRouterTests.swift
+++ b/SportsTimeTests/Planning/GameDAGRouterTests.swift
@@ -353,6 +353,36 @@ struct GameDAGRouterTests {
         #expect(!combinedRoutes.isEmpty, "NYC to Chicago over 2 days should be feasible")
     }
 
+    @Test("findRoutes: anchor routes can span gaps larger than 5 days")
+    func findRoutes_anchorRoutesAllowLongDateGaps() {
+        let today = calendar.startOfDay(for: Date())
+        let day0 = today
+        let day1 = calendar.date(byAdding: .day, value: 1, to: today)!
+        let day8 = calendar.date(byAdding: .day, value: 8, to: today)!
+
+        let sharedStadium = makeStadium(city: "New York", coord: nycCoord)
+        let bridgeStadium = makeStadium(city: "Boston", coord: bostonCoord)
+
+        let anchorStart = makeGame(stadiumId: sharedStadium.id, date: day0)
+        let bridgeGame = makeGame(stadiumId: bridgeStadium.id, date: day1)
+        let anchorEnd = makeGame(stadiumId: sharedStadium.id, date: day8)
+
+        let routes = GameDAGRouter.findRoutes(
+            games: [anchorStart, bridgeGame, anchorEnd],
+            stadiums: [sharedStadium.id: sharedStadium, bridgeStadium.id: bridgeStadium],
+            constraints: constraints,
+            anchorGameIds: [anchorStart.id, anchorEnd.id]
+        )
+
+        #expect(!routes.isEmpty, "Expected a route that includes both anchors across an 8-day gap")
+
+        for route in routes {
+            let ids = Set(route.map { $0.id })
+            #expect(ids.contains(anchorStart.id), "Route should include start anchor")
+            #expect(ids.contains(anchorEnd.id), "Route should include end anchor")
+        }
+    }
+
     // MARK: - Property Tests
 
     @Test("Property: route count never exceeds maxOptions (75)")
diff --git a/SportsTimeTests/Planning/ScenarioAPlannerTests.swift b/SportsTimeTests/Planning/ScenarioAPlannerTests.swift
index dc57ad7..314eb7a 100644
--- a/SportsTimeTests/Planning/ScenarioAPlannerTests.swift
+++ b/SportsTimeTests/Planning/ScenarioAPlannerTests.swift
@@ -220,6 +220,55 @@ struct ScenarioAPlannerTests {
         #expect(failure.reason == .noGamesInRange)
     }
 
+    @Test("plan: multiple must-stop cities are required without excluding other route games")
+    func plan_multipleMustStops_requireCoverageWithoutExclusiveFiltering() {
+        let startDate = Date()
+        let endDate = startDate.addingTimeInterval(86400 * 10)
+
+        let nycStadium = makeStadium(id: "nyc", city: "New York", coordinate: nycCoord)
+        let bostonStadium = makeStadium(id: "boston", city: "Boston", coordinate: bostonCoord)
+        let phillyStadium = makeStadium(id: "philly", city: "Philadelphia", coordinate: CLLocationCoordinate2D(latitude: 39.9526, longitude: -75.1652))
+
+        let nycGame = makeGame(id: "nyc-game", stadiumId: "nyc", dateTime: startDate.addingTimeInterval(86400 * 1))
+        let bostonGame = makeGame(id: "boston-game", stadiumId: "boston", dateTime: startDate.addingTimeInterval(86400 * 3))
+        let phillyGame = makeGame(id: "philly-game", stadiumId: "philly", dateTime: startDate.addingTimeInterval(86400 * 5))
+
+        let prefs = TripPreferences(
+            planningMode: .dateRange,
+            sports: [.mlb],
+            startDate: startDate,
+            endDate: endDate,
+            leisureLevel: .moderate,
+            mustStopLocations: [
+                LocationInput(name: "New York", coordinate: nycCoord),
+                LocationInput(name: "Boston", coordinate: bostonCoord)
+            ],
+            lodgingType: .hotel,
+            numberOfDrivers: 2
+        )
+
+        let request = PlanningRequest(
+            preferences: prefs,
+            availableGames: [nycGame, bostonGame, phillyGame],
+            teams: [:],
+            stadiums: ["nyc": nycStadium, "boston": bostonStadium, "philly": phillyStadium]
+        )
+
+        let result = planner.plan(request: request)
+
+        guard case .success(let options) = result else {
+            Issue.record("Expected success with two feasible must-stop cities")
+            return
+        }
+
+        #expect(!options.isEmpty)
+        for option in options {
+            let gameIds = Set(option.stops.flatMap { $0.games })
+            #expect(gameIds.contains("nyc-game"), "Each option should satisfy New York must-stop")
+            #expect(gameIds.contains("boston-game"), "Each option should satisfy Boston must-stop")
+        }
+    }
+
     // MARK: - Specification Tests: Successful Planning
 
     @Test("plan: single game in range returns success with one option")
diff --git a/SportsTimeTests/Planning/ScenarioBPlannerTests.swift b/SportsTimeTests/Planning/ScenarioBPlannerTests.swift
index 31e7b56..d3f2294 100644
--- a/SportsTimeTests/Planning/ScenarioBPlannerTests.swift
+++ b/SportsTimeTests/Planning/ScenarioBPlannerTests.swift
@@ -297,6 +297,49 @@ struct ScenarioBPlannerTests {
         // May also fail if no valid date ranges, which is acceptable
     }
 
+    @Test("plan: explicit date range with out-of-range selected game returns dateRangeViolation")
+    func plan_explicitDateRange_selectedGameOutsideRange_returnsDateRangeViolation() {
+        let baseDate = Date()
+        let rangeStart = baseDate
+        let rangeEnd = baseDate.addingTimeInterval(86400 * 3)
+        let outOfRangeDate = baseDate.addingTimeInterval(86400 * 10)
+
+        let stadium = makeStadium(id: "stadium1", city: "New York", coordinate: nycCoord)
+        let selectedGame = makeGame(id: "outside-anchor", stadiumId: "stadium1", dateTime: outOfRangeDate)
+
+        let prefs = TripPreferences(
+            planningMode: .dateRange,
+            sports: [.mlb],
+            mustSeeGameIds: ["outside-anchor"],
+            startDate: rangeStart,
+            endDate: rangeEnd,
+            leisureLevel: .moderate,
+            lodgingType: .hotel,
+            numberOfDrivers: 1
+        )
+
+        let request = PlanningRequest(
+            preferences: prefs,
+            availableGames: [selectedGame],
+            teams: [:],
+            stadiums: ["stadium1": stadium]
+        )
+
+        let result = planner.plan(request: request)
+
+        guard case .failure(let failure) = result else {
+            Issue.record("Expected date range violation when selected game is outside explicit range")
+            return
+        }
+
+        guard case .dateRangeViolation(let violatingGames) = failure.reason else {
+            Issue.record("Expected .dateRangeViolation, got \(failure.reason)")
+            return
+        }
+
+        #expect(Set(violatingGames.map { $0.id }) == ["outside-anchor"])
+    }
+
     // MARK: - Specification Tests: Arrival Time Validation
 
     @Test("plan: uses arrivalBeforeGameStart validator")
diff --git a/SportsTimeTests/Planning/ScenarioCPlannerTests.swift b/SportsTimeTests/Planning/ScenarioCPlannerTests.swift
index 5329931..96da2da 100644
--- a/SportsTimeTests/Planning/ScenarioCPlannerTests.swift
+++ b/SportsTimeTests/Planning/ScenarioCPlannerTests.swift
@@ -197,6 +197,47 @@ struct ScenarioCPlannerTests {
         #expect(failure.reason == .noGamesInRange)
     }
 
+    @Test("plan: city names with state suffixes match stadium city names")
+    func plan_cityNamesWithStateSuffixes_matchStadiumCities() {
+        let baseDate = Date()
+        let endDate = baseDate.addingTimeInterval(86400 * 10)
+
+        let startLocation = LocationInput(name: "Chicago, IL", coordinate: chicagoCoord)
+        let endLocation = LocationInput(name: "New York, NY", coordinate: nycCoord)
+
+        let chicagoStadium = makeStadium(id: "chicago", city: "Chicago", coordinate: chicagoCoord)
+        let nycStadium = makeStadium(id: "nyc", city: "New York", coordinate: nycCoord)
+
+        let chicagoGame = makeGame(id: "chi-game", stadiumId: "chicago", dateTime: baseDate.addingTimeInterval(86400 * 1))
+        let nycGame = makeGame(id: "nyc-game", stadiumId: "nyc", dateTime: baseDate.addingTimeInterval(86400 * 4))
+
+        let prefs = TripPreferences(
+            planningMode: .locations,
+            startLocation: startLocation,
+            endLocation: endLocation,
+            sports: [.mlb],
+            startDate: baseDate,
+            endDate: endDate,
+            leisureLevel: .moderate,
+            lodgingType: .hotel,
+            numberOfDrivers: 2
+        )
+
+        let request = PlanningRequest(
+            preferences: prefs,
+            availableGames: [chicagoGame, nycGame],
+            teams: [:],
+            stadiums: ["chicago": chicagoStadium, "nyc": nycStadium]
+        )
+
+        let result = planner.plan(request: request)
+
+        guard case .success = result else {
+            Issue.record("Expected success with city/state location labels matching plain stadium cities")
+            return
+        }
+    }
+
     // MARK: - Specification Tests: Directional Filtering
 
     @Test("plan: directional filtering includes stadiums toward destination")
diff --git a/SportsTimeTests/Planning/ScenarioDPlannerTests.swift b/SportsTimeTests/Planning/ScenarioDPlannerTests.swift
index 7a83b80..3a1e6bf 100644
--- a/SportsTimeTests/Planning/ScenarioDPlannerTests.swift
+++ b/SportsTimeTests/Planning/ScenarioDPlannerTests.swift
@@ -272,6 +272,63 @@ struct ScenarioDPlannerTests {
         #expect(!options.isEmpty)
     }
 
+    @Test("plan: useHomeLocation with startLocation adds home start and end stops")
+    func plan_useHomeLocationWithStartLocation_addsHomeEndpoints() {
+        let startDate = Date()
+        let endDate = startDate.addingTimeInterval(86400 * 10)
+
+        let homeCoord = CLLocationCoordinate2D(latitude: 39.7392, longitude: -104.9903)  // Denver
+        let homeLocation = LocationInput(name: "Denver", coordinate: homeCoord)
+
+        let bostonStadium = makeStadium(id: "boston", city: "Boston", coordinate: bostonCoord)
+        let game = Game(
+            id: "team-game",
+            homeTeamId: "red-sox",
+            awayTeamId: "yankees",
+            stadiumId: "boston",
+            dateTime: startDate.addingTimeInterval(86400 * 3),
+            sport: .mlb,
+            season: "2026",
+            isPlayoff: false
+        )
+
+        let prefs = TripPreferences(
+            planningMode: .followTeam,
+            startLocation: homeLocation,
+            sports: [.mlb],
+            startDate: startDate,
+            endDate: endDate,
+            leisureLevel: .moderate,
+            lodgingType: .hotel,
+            numberOfDrivers: 2,
+            followTeamId: "yankees",
+            useHomeLocation: true
+        )
+
+        let request = PlanningRequest(
+            preferences: prefs,
+            availableGames: [game],
+            teams: [:],
+            stadiums: ["boston": bostonStadium]
+        )
+
+        let result = planner.plan(request: request)
+
+        guard case .success(let options) = result else {
+            Issue.record("Expected success with home endpoint enabled")
+            return
+        }
+
+        #expect(!options.isEmpty)
+
+        for option in options {
+            #expect(option.stops.first?.city == "Denver")
+            #expect(option.stops.last?.city == "Denver")
+            #expect(option.stops.first?.games.isEmpty == true)
+            #expect(option.stops.last?.games.isEmpty == true)
+        }
+    }
+
     // MARK: - Invariant Tests
 
     @Test("Invariant: all returned games have team as home or away")
diff --git a/SportsTimeTests/Planning/ScenarioEPlannerTests.swift b/SportsTimeTests/Planning/ScenarioEPlannerTests.swift
index 3cc66ae..b1944c2 100644
--- a/SportsTimeTests/Planning/ScenarioEPlannerTests.swift
+++ b/SportsTimeTests/Planning/ScenarioEPlannerTests.swift
@@ -406,6 +406,146 @@ struct ScenarioEPlannerTests {
         }
     }
 
+    @Test("plan: falls back when earliest per-team anchors are infeasible")
+    func plan_fallbackWhenEarliestAnchorsInfeasible() {
+        let calendar = Calendar.current
+        let baseDate = calendar.startOfDay(for: Date())
+
+        let nycStadium = makeStadium(id: "nyc", city: "New York", coordinate: nycCoord)
+        let chicagoStadium = makeStadium(id: "chi", city: "Chicago", coordinate: chicagoCoord)
+
+        // Team A has one early game in NYC.
+        let teamAGame = makeGame(
+            id: "team-a-day1",
+            homeTeamId: "teamA",
+            awayTeamId: "opp",
+            stadiumId: "nyc",
+            dateTime: calendar.date(bySettingHour: 19, minute: 0, second: 0, of: baseDate.addingTimeInterval(86400 * 1))!
+        )
+
+        // Team B has an early game (day 2, infeasible from NYC with 1 driver),
+        // and a later game (day 4, feasible and should be selected by fallback).
+        let teamBEarly = makeGame(
+            id: "team-b-day2",
+            homeTeamId: "teamB",
+            awayTeamId: "opp",
+            stadiumId: "chi",
+            dateTime: calendar.date(bySettingHour: 19, minute: 0, second: 0, of: baseDate.addingTimeInterval(86400 * 2))!
+        )
+        let teamBLate = makeGame(
+            id: "team-b-day4",
+            homeTeamId: "teamB",
+            awayTeamId: "opp",
+            stadiumId: "chi",
+            dateTime: calendar.date(bySettingHour: 19, minute: 0, second: 0, of: baseDate.addingTimeInterval(86400 * 4))!
+        )
+
+        let prefs = TripPreferences(
+            planningMode: .teamFirst,
+            sports: [.mlb],
+            startDate: baseDate,
+            endDate: baseDate.addingTimeInterval(86400 * 30),
+            leisureLevel: .moderate,
+            lodgingType: .hotel,
+            numberOfDrivers: 1,
+            selectedTeamIds: ["teamA", "teamB"]
+        )
+
+        let request = PlanningRequest(
+            preferences: prefs,
+            availableGames: [teamAGame, teamBEarly, teamBLate],
+            teams: [
+                "teamA": makeTeam(id: "teamA", name: "Team A"),
+                "teamB": makeTeam(id: "teamB", name: "Team B")
+            ],
+            stadiums: ["nyc": nycStadium, "chi": chicagoStadium]
+        )
+
+        let result = planner.plan(request: request)
+
+        guard case .success(let options) = result else {
+            Issue.record("Expected fallback success when earliest anchor combo is infeasible")
+            return
+        }
+
+        #expect(!options.isEmpty)
+
+        let optionGameIds = options.map { Set($0.stops.flatMap { $0.games }) }
+        #expect(optionGameIds.contains { $0.contains("team-a-day1") && $0.contains("team-b-day4") },
+                "Expected at least one route that uses the later feasible Team B game")
+    }
+
+    @Test("plan: keeps date-distinct options even when city order is identical")
+    func plan_keepsDistinctGameSetsWithSameCityOrder() {
+        let calendar = Calendar.current
+        let baseDate = calendar.startOfDay(for: Date())
+
+        let nycStadium = makeStadium(id: "nyc", city: "New York", coordinate: nycCoord)
+        let bostonStadium = makeStadium(id: "boston", city: "Boston", coordinate: bostonCoord)
+
+        let teamAFirst = makeGame(
+            id: "team-a-day1",
+            homeTeamId: "teamA",
+            awayTeamId: "opp",
+            stadiumId: "nyc",
+            dateTime: calendar.date(bySettingHour: 19, minute: 0, second: 0, of: baseDate.addingTimeInterval(86400 * 1))!
+        )
+        let teamBFirst = makeGame(
+            id: "team-b-day4",
+            homeTeamId: "teamB",
+            awayTeamId: "opp",
+            stadiumId: "boston",
+            dateTime: calendar.date(bySettingHour: 19, minute: 0, second: 0, of: baseDate.addingTimeInterval(86400 * 4))!
+        )
+        let teamASecond = makeGame(
+            id: "team-a-day10",
+            homeTeamId: "teamA",
+            awayTeamId: "opp",
+            stadiumId: "nyc",
+            dateTime: calendar.date(bySettingHour: 19, minute: 0, second: 0, of: baseDate.addingTimeInterval(86400 * 10))!
+        )
+        let teamBSecond = makeGame(
+            id: "team-b-day13",
+            homeTeamId: "teamB",
+            awayTeamId: "opp",
+            stadiumId: "boston",
+            dateTime: calendar.date(bySettingHour: 19, minute: 0, second: 0, of: baseDate.addingTimeInterval(86400 * 13))!
+        )
+
+        let prefs = TripPreferences(
+            planningMode: .teamFirst,
+            sports: [.mlb],
+            startDate: baseDate,
+            endDate: baseDate.addingTimeInterval(86400 * 30),
+            leisureLevel: .moderate,
+            lodgingType: .hotel,
+            numberOfDrivers: 2,
+            selectedTeamIds: ["teamA", "teamB"]
+        )
+
+        let request = PlanningRequest(
+            preferences: prefs,
+            availableGames: [teamAFirst, teamBFirst, teamASecond, teamBSecond],
+            teams: [
+                "teamA": makeTeam(id: "teamA", name: "Team A"),
+                "teamB": makeTeam(id: "teamB", name: "Team B")
+            ],
+            stadiums: ["nyc": nycStadium, "boston": bostonStadium]
+        )
+
+        let result = planner.plan(request: request)
+
+        guard case .success(let options) = result else {
+            Issue.record("Expected success for repeated city-order windows")
+            return
+        }
+
+        let uniqueGameSets = Set(options.map { option in
+            option.stops.flatMap { $0.games }.sorted().joined(separator: "-")
+        })
+        #expect(uniqueGameSets.count >= 2, "Expected distinct date/game combinations to survive deduplication")
+    }
+
     @Test("plan: routes sorted by duration ascending")
     func plan_routesSortedByDurationAscending() {
         let baseDate = Date()