diff --git a/oAI/Resources/Confab.help/Contents/Resources/en.lproj/index.html b/oAI/Resources/Confab.help/Contents/Resources/en.lproj/index.html
index b26dd5b..2a9ca30 100644
--- a/oAI/Resources/Confab.help/Contents/Resources/en.lproj/index.html
+++ b/oAI/Resources/Confab.help/Contents/Resources/en.lproj/index.html
@@ -716,6 +716,10 @@ The weather is sunny today!
                 <div class="example">
                     <pre><code>~/Library/Application Support/oAI/sync/
 ├── README.md                    # Warning about manual edits
+├── folders.json                 # Your folder structure (auto-managed, don't edit)
+├── notes.json                   # Per-conversation notes index (auto-managed, don't edit)
+├── notes/                       # Per-conversation notes files
+│   └── ...
 └── conversations/
     ├── my-first-chat.md
     ├── python-help.md
@@ -773,6 +777,16 @@ The weather is sunny today!
                     <li>Check footer for detailed error message</li>
                 </ul>
 
+                <h4 id="git-sync-troubleshooting-untracked">"Untracked Working Tree Files Would Be Overwritten"</h4>
+                <p>This can happen the first time a machine syncs after Confab adds a new file to the sync repository (like <code>folders.json</code> or <code>notes.json</code>) — if that file gets written locally before this machine has ever pulled it from the remote, git sees it as a leftover, unrelated file blocking the merge.</p>
+                <p>When Confab detects this specific error, it offers to fix it automatically — a dialog appears with a <strong>"Fix It For Me"</strong> button that removes the leftover local copy and completes the sync, or a <strong>"Fix It Myself"</strong> button if you'd rather do it by hand:</p>
+                <ol>
+                    <li>Open your sync folder (default: <code>~/Library/Application Support/oAI/sync</code>)</li>
+                    <li>Delete the specific file(s) named in the error message</li>
+                    <li>Open Terminal, <code>cd</code> into that folder, and run <code>git pull --ff-only</code> once</li>
+                    <li>Confab will regenerate the file correctly on its next sync</li>
+                </ol>
+
                 <h4>Merge Conflicts</h4>
                 <ul>
                     <li>Stop auto-sync on all but one machine</li>
diff --git a/oAI/Services/GitSyncService.swift b/oAI/Services/GitSyncService.swift
index 3f9075b..a183c1d 100644
--- a/oAI/Services/GitSyncService.swift
+++ b/oAI/Services/GitSyncService.swift
@@ -33,6 +33,17 @@ class GitSyncService {
     // Debounce tracking
     private var pendingSyncTask: Task<Void, Never>?
 
+    /// A pull failed because a new sync-repo file (folders.json, notes.json, ...) collided with an
+    /// untracked local copy — see parseUntrackedFileConflict(from:). Surfaced to the user via
+    /// GitSyncConflictSheet (wired in ChatView.swift), offering an automatic or manual fix.
+    struct PendingGitConflict: Identifiable {
+        let id = UUID()
+        let files: [String]
+        let rawError: String
+        var canAutoFix: Bool { files.allSatisfy(GitSyncService.isFileSafeToAutoDelete) }
+    }
+    private(set) var pendingGitConflict: PendingGitConflict? = nil
+
     private init() {
         // Check if repository is cloned at initialization (synchronous check)
         let localPath = expandPath(settings.syncLocalPath)
@@ -83,12 +94,84 @@ class GitSyncService {
         let localPath = expandPath(settings.syncLocalPath)
         log.info("Pulling changes from remote")
 
-        _ = try await runGit(["pull", "--ff-only"], cwd: localPath)
+        do {
+            _ = try await runGit(["pull", "--ff-only"], cwd: localPath)
+        } catch {
+            // Surface an "untracked working tree files" collision as a recoverable conflict the
+            // user can act on, without changing this function's throw contract — existing callers
+            // (syncOnStartup's non-fatal log, syncNow's error display) are unaffected. Guarded on
+            // pendingGitConflict already being nil so a second pull failure while the sheet is
+            // still showing doesn't replace its content out from under the user.
+            if pendingGitConflict == nil,
+               let files = Self.parseUntrackedFileConflict(from: error.localizedDescription) {
+                pendingGitConflict = PendingGitConflict(files: files, rawError: error.localizedDescription)
+            }
+            throw error
+        }
         syncStatus.lastSyncTime = Date()
 
         await updateStatus()
     }
 
+    /// Re-verifies each file is still genuinely untracked (not just trusting the parsed error text)
+    /// immediately before deleting, deletes them, retries pull(), and on success imports so the
+    /// previously-blocked content actually lands. Returns nil on success, an error description on
+    /// failure. Deliberately does not touch pendingGitConflict itself — dismissPendingGitConflict()
+    /// is the sheet's explicit "I'm done looking at this" signal. SwiftUI's .sheet(item:) dismisses
+    /// the instant pendingGitConflict goes nil, so clearing it here would yank the sheet away before
+    /// the user ever sees whether the fix actually worked.
+    func autoResolveUntrackedConflict(_ conflict: PendingGitConflict) async -> String? {
+        guard conflict.canAutoFix else {
+            return "Some of these files can't be safely removed automatically."
+        }
+
+        let localPath = expandPath(settings.syncLocalPath)
+
+        for file in conflict.files {
+            guard let status = try? await runGit(["status", "--porcelain", "--", file], cwd: localPath),
+                  status.trimmingCharacters(in: .whitespacesAndNewlines).hasPrefix("??")
+            else {
+                return "\(file) is no longer untracked — leaving it in place rather than risk deleting something else. Try syncing again."
+            }
+            try? FileManager.default.removeItem(at: URL(fileURLWithPath: localPath).appendingPathComponent(file))
+        }
+
+        do {
+            try await pull()
+            _ = try await importAllConversations()
+            return nil
+        } catch {
+            return error.localizedDescription
+        }
+    }
+
+    /// Explicit dismiss for GitSyncConflictSheet — see autoResolveUntrackedConflict's note on why
+    /// the recovery method itself never clears this.
+    func dismissPendingGitConflict() {
+        pendingGitConflict = nil
+    }
+
+    /// Shown by GitSyncManualFixSheet when the user picks "Fix It Myself" on GitSyncConflictSheet.
+    /// Deliberately in-app text rather than a deep link into the Help Book: NSWorkspace.shared.open()
+    /// silently drops the #fragment for file:// URLs before handing off to the default browser (the
+    /// anchor never survives — confirmed by inspecting location.hash in the opened page, it comes
+    /// back empty), so an anchored Help Book link always lands on the index instead of the relevant
+    /// section. Carrying the conflict's own file list and the real sync path into this sheet is also
+    /// just more useful than generic help-page prose pointing at "the file(s) named in the error".
+    private(set) var pendingManualFixInstructions: PendingGitConflict? = nil
+
+    /// Swaps GitSyncConflictSheet for GitSyncManualFixSheet — clearing pendingGitConflict here (rather
+    /// than relying on the sheet's own onDismiss) dismisses the first sheet via its .sheet(item:)
+    /// binding while pendingManualFixInstructions immediately presents the second.
+    func showManualFixInstructions(for conflict: PendingGitConflict) {
+        pendingGitConflict = nil
+        pendingManualFixInstructions = conflict
+    }
+
+    func dismissManualFixInstructions() {
+        pendingManualFixInstructions = nil
+    }
+
     /// Push local changes to remote
     func push(message: String = "Sync from Confab") async throws {
         try ensureCloned()
@@ -299,6 +382,46 @@ class GitSyncService {
         return localFolderIds.filter { !manifestFolderIds.contains($0) }
     }
 
+    // MARK: - Untracked File Conflict Recovery
+
+    /// Parses git's "untracked working tree files would be overwritten by merge" pull failure into
+    /// the list of colliding relative paths. Returns nil for any other error (auth, network, a real
+    /// merge conflict) — those aren't what this recovery flow is for. Exact git format:
+    /// "error: The following untracked working tree files would be overwritten by merge:\n\t<file>\n...\nPlease move or remove them before you merge.\nAborting"
+    nonisolated static func parseUntrackedFileConflict(from message: String) -> [String]? {
+        let marker = "untracked working tree files would be overwritten by merge:"
+        guard let markerRange = message.range(of: marker) else { return nil }
+
+        let lines = message[markerRange.upperBound...].components(separatedBy: "\n")
+        var files: [String] = []
+        for line in lines {
+            let trimmed = line.trimmingCharacters(in: .whitespaces)
+            if trimmed.isEmpty { continue }
+            // The file list ends at the first line that isn't an indented filename (git's own
+            // trailing "Please move or remove them..."/"Aborting" lines aren't tab-indented).
+            guard line.hasPrefix("\t") || line.hasPrefix("    ") else { break }
+            files.append(trimmed)
+        }
+        return files.isEmpty ? nil : files
+    }
+
+    /// Defense in depth for the "Fix It For Me" auto-recovery path: only files this app itself is
+    /// known to write into the sync repo are ever eligible for automatic deletion. Rejects path
+    /// traversal, absolute paths, and anything outside the known shape — an unrecognized file falls
+    /// back to manual recovery only (see PendingGitConflict.canAutoFix).
+    nonisolated static func isFileSafeToAutoDelete(_ relativePath: String) -> Bool {
+        if relativePath == "folders.json" || relativePath == "notes.json" {
+            return true
+        }
+        for prefix in ["conversations/", "notes/"] {
+            guard relativePath.hasPrefix(prefix) else { continue }
+            let rest = relativePath.dropFirst(prefix.count)
+            // Exactly one path segment (no further "/"), and a .md file.
+            return !rest.isEmpty && !rest.contains("/") && rest.hasSuffix(".md")
+        }
+        return false
+    }
+
     /// Import conversations from markdown files
     func importAllConversations() async throws -> (imported: Int, skipped: Int, errors: Int) {
         try ensureCloned()
diff --git a/oAI/Views/Main/ChatView.swift b/oAI/Views/Main/ChatView.swift
index 8a67c20..c993c92 100644
--- a/oAI/Views/Main/ChatView.swift
+++ b/oAI/Views/Main/ChatView.swift
@@ -131,6 +131,27 @@ struct ChatView: View {
                 onDeny: { MCPService.shared.denyPendingPersonalDataAction() }
             )
         }
+        .sheet(item: Binding(
+            get: { GitSyncService.shared.pendingGitConflict },
+            set: { _ in }
+        )) { pending in
+            GitSyncConflictSheet(
+                pending: pending,
+                onFixForMe: { await GitSyncService.shared.autoResolveUntrackedConflict(pending) },
+                onFixMyself: { GitSyncService.shared.showManualFixInstructions(for: pending) },
+                onDismiss: { GitSyncService.shared.dismissPendingGitConflict() }
+            )
+        }
+        .sheet(item: Binding(
+            get: { GitSyncService.shared.pendingManualFixInstructions },
+            set: { _ in }
+        )) { pending in
+            GitSyncManualFixSheet(
+                files: pending.files,
+                syncPath: SettingsService.shared.syncLocalPath,
+                onDone: { GitSyncService.shared.dismissManualFixInstructions() }
+            )
+        }
     }
 }
 
diff --git a/oAI/Views/Main/SidebarView.swift b/oAI/Views/Main/SidebarView.swift
index fa16e59..659e2ad 100644
--- a/oAI/Views/Main/SidebarView.swift
+++ b/oAI/Views/Main/SidebarView.swift
@@ -192,7 +192,7 @@ struct SidebarView: View {
                                 Section {
                                     if !collapsedFolders.contains(entry.folder.id) {
                                         ForEach(folderConversations) { conversation in
-                                            conversationRow(conversation)
+                                            conversationRow(conversation, depth: entry.depth + 1)
                                         }
                                     }
                                 } header: {
@@ -320,8 +320,9 @@ struct SidebarView: View {
     }
 
     @ViewBuilder
-    private func conversationRow(_ conversation: Conversation) -> some View {
+    private func conversationRow(_ conversation: Conversation, depth: Int = 0) -> some View {
         SidebarConversationRow(conversation: conversation)
+            .padding(.leading, CGFloat(depth) * 14)
             .contentShape(Rectangle())
             .onTapGesture(count: 2) {
                 chatViewModel.loadConversation(conversation)
diff --git a/oAI/Views/Screens/ConversationListView.swift b/oAI/Views/Screens/ConversationListView.swift
index 8f61b24..17f2656 100644
--- a/oAI/Views/Screens/ConversationListView.swift
+++ b/oAI/Views/Screens/ConversationListView.swift
@@ -266,7 +266,7 @@ struct ConversationListView: View {
                                         Section {
                                             if !collapsedFolders.contains(entry.folder.id) {
                                                 ForEach(folderConversations) { conversation in
-                                                    conversationRow(conversation)
+                                                    conversationRow(conversation, depth: entry.depth + 1)
                                                 }
                                             }
                                         } header: {
@@ -337,7 +337,7 @@ struct ConversationListView: View {
     }
 
     @ViewBuilder
-    private func conversationRow(_ conversation: Conversation) -> some View {
+    private func conversationRow(_ conversation: Conversation, depth: Int = 0) -> some View {
         let index = filteredConversations.firstIndex(where: { $0.id == conversation.id }) ?? 0
         HStack(spacing: 12) {
             if isSelecting {
@@ -382,6 +382,7 @@ struct ConversationListView: View {
                 .help("Delete conversation")
             }
         }
+        .padding(.leading, CGFloat(depth) * 14)
         .listRowBackground(
             !isSelecting && index == selectedIndex
                 ? Color.confabAccent.opacity(0.15)
diff --git a/oAI/Views/Screens/GitSyncConflictSheet.swift b/oAI/Views/Screens/GitSyncConflictSheet.swift
new file mode 100644
index 0000000..cb10975
--- /dev/null
+++ b/oAI/Views/Screens/GitSyncConflictSheet.swift
@@ -0,0 +1,176 @@
+//
+//  GitSyncConflictSheet.swift
+//  Confab
+//
+//  Recovery UI for Git Sync's "untracked working tree files" pull failure
+//
+// SPDX-License-Identifier: PolyForm-Noncommercial-1.0.0
+// Copyright (C) 2026 Rune Olsen
+//
+// This file is part of Confab.
+//
+// Confab is licensed under the PolyForm Noncommercial License 1.0.0.
+// You may use, study, modify, and share it for any noncommercial
+// purpose. Commercial use — including selling Confab or any part of
+// it, standalone or bundled into another product or service —
+// requires a separate commercial license from the copyright holder.
+//
+// See the LICENSE file or
+// <https://polyformproject.org/licenses/noncommercial/1.0.0> for
+// the full license text. For commercial licensing, contact Rune
+// Olsen via <https://confab.no>.
+
+
+import SwiftUI
+
+struct GitSyncConflictSheet: View {
+    let pending: GitSyncService.PendingGitConflict
+    /// Performs the automatic fix; nil return means success.
+    let onFixForMe: () async -> String?
+    /// Swaps this sheet for GitSyncManualFixSheet's in-app step-by-step instructions.
+    let onFixMyself: () -> Void
+    let onDismiss: () -> Void
+
+    private enum RecoveryState: Equatable {
+        case idle
+        case fixing
+        case succeeded
+        case failed(String)
+    }
+
+    @State private var recoveryState: RecoveryState = .idle
+
+    var body: some View {
+        VStack(alignment: .leading, spacing: 20) {
+            // Header
+            HStack(spacing: 12) {
+                Image(systemName: "exclamationmark.arrow.triangle.2.circlepath")
+                    .font(.title2)
+                    .foregroundStyle(.orange)
+                VStack(alignment: .leading, spacing: 2) {
+                    Text("Sync Ran Into a Conflict")
+                        .font(.system(size: 17, weight: .semibold))
+                    Text("Confab syncs in the background automatically, and just hit a file that collided with a leftover local copy of itself")
+                        .font(.system(size: 13))
+                        .foregroundStyle(.secondary)
+                        .fixedSize(horizontal: false, vertical: true)
+                }
+                Spacer()
+            }
+
+            // Conflicting files
+            VStack(alignment: .leading, spacing: 6) {
+                Text("AFFECTED FILES")
+                    .font(.system(size: 11, weight: .medium))
+                    .foregroundStyle(.secondary)
+                VStack(alignment: .leading, spacing: 4) {
+                    ForEach(pending.files, id: \.self) { file in
+                        Text(file)
+                            .font(.system(size: 13, design: .monospaced))
+                    }
+                }
+                .frame(maxWidth: .infinity, alignment: .leading)
+                .textSelection(.enabled)
+                .padding(12)
+                .background(Color.secondary.opacity(0.08))
+                .clipShape(RoundedRectangle(cornerRadius: 8))
+                .overlay(
+                    RoundedRectangle(cornerRadius: 8)
+                        .stroke(Color.secondary.opacity(0.2), lineWidth: 1)
+                )
+            }
+
+            Text("These are Confab's own sync bookkeeping files, not your conversations — nothing you've written is at risk either way.")
+                .font(.system(size: 12))
+                .foregroundStyle(.secondary)
+                .fixedSize(horizontal: false, vertical: true)
+
+            statusBanner
+
+            if !pending.canAutoFix {
+                HStack(alignment: .top, spacing: 8) {
+                    Image(systemName: "exclamationmark.triangle.fill")
+                        .foregroundStyle(.orange)
+                        .font(.system(size: 13))
+                        .padding(.top, 1)
+                    Text("One or more of these files aren't ones Confab recognizes as safe to remove automatically — please fix this one yourself.")
+                        .font(.system(size: 12))
+                        .foregroundStyle(.secondary)
+                        .fixedSize(horizontal: false, vertical: true)
+                }
+                .padding(10)
+                .background(Color.orange.opacity(0.08))
+                .clipShape(RoundedRectangle(cornerRadius: 8))
+            }
+
+            // Buttons
+            HStack(spacing: 8) {
+                Button("Fix It Myself") {
+                    onFixMyself()
+                }
+                .buttonStyle(.bordered)
+                .keyboardShortcut(.escape, modifiers: [])
+
+                Spacer()
+
+                if recoveryState == .succeeded {
+                    Button("Done") {
+                        onDismiss()
+                    }
+                    .buttonStyle(.borderedProminent)
+                    .keyboardShortcut(.return, modifiers: [])
+                } else {
+                    Button("Fix It For Me") {
+                        recoveryState = .fixing
+                        Task {
+                            if let errorMessage = await onFixForMe() {
+                                recoveryState = .failed(errorMessage)
+                            } else {
+                                recoveryState = .succeeded
+                            }
+                        }
+                    }
+                    .buttonStyle(.borderedProminent)
+                    .disabled(!pending.canAutoFix || recoveryState == .fixing)
+                    .keyboardShortcut(.return, modifiers: [])
+                }
+            }
+        }
+        .padding(24)
+        .frame(width: 480)
+    }
+
+    @ViewBuilder
+    private var statusBanner: some View {
+        switch recoveryState {
+        case .idle:
+            EmptyView()
+        case .fixing:
+            HStack(spacing: 8) {
+                ProgressView().controlSize(.small)
+                Text("Fixing...")
+                    .font(.system(size: 13))
+                    .foregroundStyle(.secondary)
+            }
+        case .succeeded:
+            HStack(spacing: 8) {
+                Image(systemName: "checkmark.circle.fill")
+                    .foregroundStyle(.green)
+                Text("Fixed — your conversations are back in sync.")
+                    .font(.system(size: 13))
+                    .foregroundStyle(.secondary)
+            }
+        case .failed(let message):
+            HStack(alignment: .top, spacing: 8) {
+                Image(systemName: "xmark.circle.fill")
+                    .foregroundStyle(.red)
+                    .font(.system(size: 13))
+                    .padding(.top, 1)
+                Text("Still couldn't sync: \(message)")
+                    .font(.system(size: 12))
+                    .foregroundStyle(.secondary)
+                    .fixedSize(horizontal: false, vertical: true)
+            }
+        }
+    }
+}
diff --git a/oAI/Views/Screens/GitSyncManualFixSheet.swift b/oAI/Views/Screens/GitSyncManualFixSheet.swift
new file mode 100644
index 0000000..bdc207f
--- /dev/null
+++ b/oAI/Views/Screens/GitSyncManualFixSheet.swift
@@ -0,0 +1,108 @@
+//
+//  GitSyncManualFixSheet.swift
+//  Confab
+//
+//  Manual-fix instructions for Git Sync's "untracked working tree files" pull failure —
+//  shown in-app instead of deep-linking to the Help Book (NSWorkspace.shared.open() drops
+//  #fragment anchors on file:// URLs, so an anchored help link always landed on the index).
+//
+// SPDX-License-Identifier: PolyForm-Noncommercial-1.0.0
+// Copyright (C) 2026 Rune Olsen
+//
+// This file is part of Confab.
+//
+// Confab is licensed under the PolyForm Noncommercial License 1.0.0.
+// You may use, study, modify, and share it for any noncommercial
+// purpose. Commercial use — including selling Confab or any part of
+// it, standalone or bundled into another product or service —
+// requires a separate commercial license from the copyright holder.
+//
+// See the LICENSE file or
+// <https://polyformproject.org/licenses/noncommercial/1.0.0> for
+// the full license text. For commercial licensing, contact Rune
+// Olsen via <https://confab.no>.
+
+
+import SwiftUI
+
+struct GitSyncManualFixSheet: View {
+    let files: [String]
+    let syncPath: String
+    let onDone: () -> Void
+
+    var body: some View {
+        VStack(alignment: .leading, spacing: 20) {
+            HStack(spacing: 12) {
+                Image(systemName: "wrench.and.screwdriver")
+                    .font(.title2)
+                    .foregroundStyle(.secondary)
+                VStack(alignment: .leading, spacing: 2) {
+                    Text("Fix It Yourself")
+                        .font(.system(size: 17, weight: .semibold))
+                    Text("Four steps, then Confab takes over again")
+                        .font(.system(size: 13))
+                        .foregroundStyle(.secondary)
+                }
+                Spacer()
+            }
+
+            VStack(alignment: .leading, spacing: 14) {
+                step(1, "Open your sync folder:")
+                Text(syncPath)
+                    .font(.system(size: 13, design: .monospaced))
+                    .textSelection(.enabled)
+                    .padding(10)
+                    .frame(maxWidth: .infinity, alignment: .leading)
+                    .background(Color.secondary.opacity(0.08))
+                    .clipShape(RoundedRectangle(cornerRadius: 8))
+
+                step(2, "Delete the file\(files.count == 1 ? "" : "s") named in the error:")
+                VStack(alignment: .leading, spacing: 4) {
+                    ForEach(files, id: \.self) { file in
+                        Text(file)
+                            .font(.system(size: 13, design: .monospaced))
+                    }
+                }
+                .textSelection(.enabled)
+                .padding(10)
+                .frame(maxWidth: .infinity, alignment: .leading)
+                .background(Color.secondary.opacity(0.08))
+                .clipShape(RoundedRectangle(cornerRadius: 8))
+
+                step(3, "Open Terminal, cd into that folder, and run this once:")
+                Text("git pull --ff-only")
+                    .font(.system(size: 13, design: .monospaced))
+                    .textSelection(.enabled)
+                    .padding(10)
+                    .frame(maxWidth: .infinity, alignment: .leading)
+                    .background(Color.secondary.opacity(0.08))
+                    .clipShape(RoundedRectangle(cornerRadius: 8))
+
+                step(4, "That's it — Confab will regenerate the file correctly on its next sync.")
+            }
+
+            HStack {
+                Spacer()
+                Button("Done") {
+                    onDone()
+                }
+                .buttonStyle(.borderedProminent)
+                .keyboardShortcut(.return, modifiers: [])
+            }
+        }
+        .padding(24)
+        .frame(width: 480)
+    }
+
+    @ViewBuilder
+    private func step(_ number: Int, _ text: String) -> some View {
+        HStack(alignment: .firstTextBaseline, spacing: 8) {
+            Text("\(number).")
+                .font(.system(size: 13, weight: .semibold))
+                .foregroundStyle(.secondary)
+            Text(text)
+                .font(.system(size: 13))
+                .fixedSize(horizontal: false, vertical: true)
+        }
+    }
+}
diff --git a/oAI/Views/Screens/SettingsView.swift b/oAI/Views/Screens/SettingsView.swift
index 55dcda0..d0cc9c1 100644
--- a/oAI/Views/Screens/SettingsView.swift
+++ b/oAI/Views/Screens/SettingsView.swift
@@ -237,6 +237,33 @@ It's better to admit "I need more information" or "I cannot do that" than to fak
         .sheet(isPresented: $showEmailLog) {
             EmailLogView()
         }
+        // Duplicated (not moved) from ChatView.swift: SwiftUI won't stack a new sheet on top of
+        // this already-presented Settings sheet if the .sheet(item:) only lives on ChatView, which
+        // sits underneath/behind Settings once it's open — a conflict triggered by the "Sync Now"
+        // button in here would be silently dropped with no visible modal. Attaching the same
+        // binding here too lets it present correctly regardless of which one is on top; only the
+        // currently-frontmost host actually shows it, so there's no double-presentation risk.
+        .sheet(item: Binding(
+            get: { gitSync.pendingGitConflict },
+            set: { _ in }
+        )) { pending in
+            GitSyncConflictSheet(
+                pending: pending,
+                onFixForMe: { await gitSync.autoResolveUntrackedConflict(pending) },
+                onFixMyself: { gitSync.showManualFixInstructions(for: pending) },
+                onDismiss: { gitSync.dismissPendingGitConflict() }
+            )
+        }
+        .sheet(item: Binding(
+            get: { gitSync.pendingManualFixInstructions },
+            set: { _ in }
+        )) { pending in
+            GitSyncManualFixSheet(
+                files: pending.files,
+                syncPath: SettingsService.shared.syncLocalPath,
+                onDone: { gitSync.dismissManualFixInstructions() }
+            )
+        }
         .fileImporter(
             isPresented: $showRestoreFilePicker,
             allowedContentTypes: [.json],
diff --git a/oAI/oAIApp.swift b/oAI/oAIApp.swift
index d93c0a3..f74a147 100644
--- a/oAI/oAIApp.swift
+++ b/oAI/oAIApp.swift
@@ -206,7 +206,7 @@ struct oAIApp: App {
 
             // ── Help menu ─────────────────────────────────────────────────
             CommandGroup(replacing: .help) {
-                Button("Confab Help") { openHelp() }
+                Button("Confab Help") { Self.openHelpBook() }
                     .keyboardShortcut("?", modifiers: .command)
                 Divider()
                 Button("Read Release Notes") {
@@ -223,14 +223,18 @@ struct oAIApp: App {
     }
 
     #if os(macOS)
-    private func openHelp() {
-        // Opens the Help Book's index.html directly in the default browser rather than
-        // through NSHelpManager/Help Viewer — see CLAUDE.md's macOS 27 beta note for why
-        // (Apple's Tips.app replacement for Help Viewer can't resolve anchors on this beta).
-        // Revisit once macOS 27 reaches RC.
-        if let helpBookURL = Bundle.main.url(forResource: "Confab.help", withExtension: nil) {
-            NSWorkspace.shared.open(helpBookURL.appendingPathComponent("Contents/Resources/en.lproj/index.html"))
-        }
+    /// Opens the Help Book's index.html directly in the default browser rather than through
+    /// NSHelpManager/Help Viewer — see CLAUDE.md's macOS 27 beta note for why (Apple's Tips.app
+    /// replacement for Help Viewer can't resolve anchors on this beta). Revisit once macOS 27
+    /// reaches RC. No anchor/fragment support: NSWorkspace.shared.open() silently drops #fragments
+    /// for file:// URLs before handing off to the browser (confirmed via location.hash coming back
+    /// empty in the opened page) — deep links into a specific section aren't reliable through this
+    /// API, so callers needing to point at specific content should show it in-app instead (see
+    /// GitSyncManualFixSheet for an example) rather than trying to anchor into this Help Book.
+    nonisolated static func openHelpBook() {
+        guard let helpBookURL = Bundle.main.url(forResource: "Confab.help", withExtension: nil) else { return }
+        let url = helpBookURL.appendingPathComponent("Contents/Resources/en.lproj/index.html")
+        NSWorkspace.shared.open(url)
     }
     #endif
 }
diff --git a/oAITests/GitSyncServiceTests.swift b/oAITests/GitSyncServiceTests.swift
index 9c2f880..deff04c 100644
--- a/oAITests/GitSyncServiceTests.swift
+++ b/oAITests/GitSyncServiceTests.swift
@@ -285,4 +285,71 @@ struct GitSyncServiceTests {
         #expect(decoded.notes[conversationId]?.filename == "Chat-a3f2.md")
         #expect(decoded.notes[conversationId]?.enabled == true)
     }
+
+    // MARK: - parseUntrackedFileConflict
+
+    @Test("Parses a single colliding file out of git's untracked-files error")
+    func parseUntrackedFileConflictSingleFile() {
+        let message = "error: The following untracked working tree files would be overwritten by merge:\n\tfolders.json\nPlease move or remove them before you merge.\nAborting"
+        #expect(GitSyncService.parseUntrackedFileConflict(from: message) == ["folders.json"])
+    }
+
+    @Test("Parses multiple colliding files out of git's untracked-files error")
+    func parseUntrackedFileConflictMultipleFiles() {
+        let message = "error: The following untracked working tree files would be overwritten by merge:\n\tfolders.json\n\tnotes.json\nPlease move or remove them before you merge.\nAborting"
+        #expect(GitSyncService.parseUntrackedFileConflict(from: message) == ["folders.json", "notes.json"])
+    }
+
+    @Test("Wrapped SyncError.gitFailed description still parses correctly")
+    func parseUntrackedFileConflictWrappedMessage() {
+        let message = "Git command failed: error: The following untracked working tree files would be overwritten by merge:\n\tnotes/Chat-a3f2.md\nPlease move or remove them before you merge.\nAborting"
+        #expect(GitSyncService.parseUntrackedFileConflict(from: message) == ["notes/Chat-a3f2.md"])
+    }
+
+    @Test("Unrelated git errors return nil, not an empty or bogus file list")
+    func parseUntrackedFileConflictUnrelatedErrors() {
+        #expect(GitSyncService.parseUntrackedFileConflict(from: "fatal: Authentication failed for 'https://gitlab.pm/rune/oai-swift.git/'") == nil)
+        #expect(GitSyncService.parseUntrackedFileConflict(from: "fatal: unable to access: Could not resolve host") == nil)
+        #expect(GitSyncService.parseUntrackedFileConflict(from: "error: Your local changes to the following files would be overwritten by merge:\n\tconversations/x.md") == nil)
+    }
+
+    // MARK: - isFileSafeToAutoDelete
+
+    @Test("Known sync-manifest files are safe to auto-delete")
+    func isFileSafeToAutoDeleteAllowsKnownFiles() {
+        #expect(GitSyncService.isFileSafeToAutoDelete("folders.json"))
+        #expect(GitSyncService.isFileSafeToAutoDelete("notes.json"))
+        #expect(GitSyncService.isFileSafeToAutoDelete("conversations/my-chat.md"))
+        #expect(GitSyncService.isFileSafeToAutoDelete("notes/Chat-a3f2.md"))
+    }
+
+    @Test("Path traversal and absolute paths are never safe to auto-delete")
+    func isFileSafeToAutoDeleteRejectsTraversal() {
+        #expect(!GitSyncService.isFileSafeToAutoDelete("../etc/passwd"))
+        #expect(!GitSyncService.isFileSafeToAutoDelete("/etc/passwd"))
+        #expect(!GitSyncService.isFileSafeToAutoDelete("conversations/../../../etc/passwd"))
+    }
+
+    @Test("Files outside the known shape are never safe to auto-delete")
+    func isFileSafeToAutoDeleteRejectsUnknownFiles() {
+        #expect(!GitSyncService.isFileSafeToAutoDelete("README.md"))
+        #expect(!GitSyncService.isFileSafeToAutoDelete("conversations/sub/x.md"))
+        #expect(!GitSyncService.isFileSafeToAutoDelete("notes/sub/x.md"))
+        #expect(!GitSyncService.isFileSafeToAutoDelete(""))
+        #expect(!GitSyncService.isFileSafeToAutoDelete("conversations/"))
+    }
+
+    // MARK: - PendingGitConflict.canAutoFix
+
+    @Test("canAutoFix is true when every file is safe to auto-delete")
+    func pendingGitConflictCanAutoFixAllSafe() {
+        let conflict = GitSyncService.PendingGitConflict(files: ["folders.json", "notes.json"], rawError: "")
+        #expect(conflict.canAutoFix)
+    }
+
+    @Test("canAutoFix is false when any file isn't safe to auto-delete")
+    func pendingGitConflictCanAutoFixOneUnsafe() {
+        let conflict = GitSyncService.PendingGitConflict(files: ["folders.json", "README.md"], rawError: "")
+        #expect(!conflict.canAutoFix)
+    }
 }