Merge claudedo/1f4f59b14e4d481d97e843b6b2014af5

docs/explore-notes/conpty-sessions.md

@@ -1,7 +1,7 @@
 # ConPTY interactive sessions & launch specs
 
 > **Explore-note — verify before trusting.** Distilled map of a subsystem, not authoritative.
-> Last verified against commit `aac84e4` (2026-08-06).
+> Last verified against commit `1a988ff` (2026-08-06).
 > Drift check: `git log --oneline bdee731..HEAD -- src/ClaudeDo.Worker/Planning src/ClaudeDo.Worker/Hub src/ClaudeDo.Worker/Runner/ClaudeArgsBuilder.cs src/ClaudeDo.Ui/ViewModels/MissionControlViewModel.cs src/ClaudeDo.Ui/Views/InteractiveTerminalView.axaml`
 > Stable structure only (no line numbers). See docs/explore-notes/README.md.
 
@@ -35,7 +35,7 @@ Two independent reasons:
 
 A fresh task session's brief lives at `~/.todo-app/task-sessions/<taskId>/brief.md`
 (`InteractiveLaunchSpecService.BuildFreshTaskArgsAsync`). A task with neither title nor
-description skips the file **and** the positional arg entirely.
+description skips the file **and** the positional arg entirely — it still gets `--session-id`.
 
 ## Argument ordering
 
@@ -46,6 +46,34 @@ except for a fresh task session with a brief, where `--add-dir <sessionDir>` mus
 `--model` is deliberately **NOT** forced on an interactive session — the user can still switch
 models in the TUI.
 
+## Resuming a task session (`TaskEntity.InteractiveSessionId`)
+
+`claude --session-id <uuid>` lets the caller pre-assign a conversation's session id instead of
+waiting for the CLI to generate one. `BuildForTaskAsync` uses this so a closed or aborted
+interactive task session can be resumed even if it never got far enough to write anything to its
+own transcript:
+
+1. **Resume check.** If the task isn't on a freshly (re)created worktree, `BuildForTaskAsync`
+   picks a session to resume with `task.InteractiveSessionId ?? run?.SessionId` — this task's own
+   last *interactive* conversation takes precedence over the latest *autonomous* run's session,
+   since they're distinct conversations even against the same worktree. A task that has only ever
+   run autonomously still resumes into that run's session the first time it's opened interactively
+   (this is the pre-existing behavior `run?.SessionId` alone used to provide).
+2. **Fresh path.** If neither is available (never run any way, or `isFreshWorktree`), a new
+   `Guid.NewGuid()` is generated and persisted to `TaskEntity.InteractiveSessionId` via
+   `TaskRepository.SetInteractiveSessionIdAsync` — **before** the `LaunchSpec` is returned, i.e.
+   before the ConPTY host ever spawns `claude`. `BuildFreshTaskArgsAsync` then passes it as
+   `--session-id <guid>`, placed as the single-value flag directly before the positional kickoff
+   (or, with no brief, right after `--effort`).
+3. **Fresh worktree wins.** `isFreshWorktree` forces `run` to `null` *and* is checked before
+   reading `task.InteractiveSessionId`, so a recreated worktree never resumes a stale id from
+   either source — it always takes the fresh path, which overwrites the stale
+   `InteractiveSessionId` with the new one.
+
+Net effect: reopening an interactive session for a task (pane closed, process killed, whatever)
+resumes the same claude conversation, because the id was committed to the DB before the previous
+launch even started.
+
 ## List handler ("Let Claude handle it")
 
 `BuildForMergeHelperAsync` uses `--permission-mode auto` so it runs unattended. The

src/ClaudeDo.Data/CLAUDE.md

@@ -4,9 +4,10 @@ Shared data layer: models, repositories, SQLite infrastructure, and git operatio
 
 ## Models
 
-- **TaskEntity** — Id, ListId, Title, Description, Status, PlanningPhase, BlockedByTaskId (FK to predecessor in a chain), ScheduledFor, Result, ReviewFeedback, LogPath, timestamps, CommitType, Model / SystemPrompt / AgentPath / MaxTurns (nullable overrides), IsStarred, IsMyDay, IsManual, Notes, ParentTaskId, PlanningSessionId / PlanningSessionToken / PlanningFinalizedAt, CreatedBy, HandlerBaseCommit / HandlerHeadCommit.
+- **TaskEntity** — Id, ListId, Title, Description, Status, PlanningPhase, BlockedByTaskId (FK to predecessor in a chain), ScheduledFor, Result, ReviewFeedback, LogPath, timestamps, CommitType, Model / SystemPrompt / AgentPath / MaxTurns (nullable overrides), IsStarred, IsMyDay, IsManual, Notes, ParentTaskId, PlanningSessionId / PlanningSessionToken / PlanningFinalizedAt, CreatedBy, HandlerBaseCommit / HandlerHeadCommit, InteractiveSessionId.
   - Status / PlanningPhase / BlockedByTaskId semantics + allowed transitions: `ClaudeDo.Worker/CLAUDE.md` → Status Model.
   - `HandlerBaseCommit`/`HandlerHeadCommit` = the review range for a **worktree-less "list handler" host task** ("Let Claude handle it"), which commits straight into the list's working dir instead of a per-task worktree. Everything that reads a task's diff falls back to this pair whenever `Worktree` is null → [conpty-sessions](../../docs/explore-notes/conpty-sessions.md).
+  - `InteractiveSessionId` = the claude session id an embedded ConPTY interactive task session runs under, persisted by `InteractiveLaunchSpecService` before launch so a closed/aborted session can be resumed → [conpty-sessions](../../docs/explore-notes/conpty-sessions.md).
   - Legacy status values `Manual`/`Planning`/`Planned`/`Draft`/`Waiting` were retired; existing rows backfill via the `RetireLegacyTaskStatus` migration.
 - **ListEntity** — Id, Name, WorkingDir, DefaultCommitType, CreatedAt, IsManual (reminder list — tasks created here default to `IsManual`)
 - **ListConfigEntity** — ListId (PK, 1:1), Model, SystemPrompt, AgentPath, MaxTurns, SessionSkills, VerifyCommand (all nullable). `VerifyCommand` is an optional post-merge gate; null/blank = no gate → [review-merge](../../docs/explore-notes/review-merge.md).

src/ClaudeDo.Data/Configuration/TaskEntityConfiguration.cs

@@ -95,6 +95,7 @@ public class TaskEntityConfiguration : IEntityTypeConfiguration<TaskEntity>
         builder.Property(t => t.SessionSkills).HasColumnName("session_skills");
         builder.Property(t => t.HandlerBaseCommit).HasColumnName("handler_base_commit");
         builder.Property(t => t.HandlerHeadCommit).HasColumnName("handler_head_commit");
+        builder.Property(t => t.InteractiveSessionId).HasColumnName("interactive_session_id");
 
         builder.Property(t => t.ParentTaskId).HasColumnName("parent_task_id");
         builder.Property(t => t.PlanningSessionId).HasColumnName("planning_session_id");

src/ClaudeDo.Data/Migrations/20260806111454_AddInteractiveSessionId.Designer.cs

@@ -0,0 +1,869 @@
+// <auto-generated />
+using System;
+using ClaudeDo.Data;
+using Microsoft.EntityFrameworkCore;
+using Microsoft.EntityFrameworkCore.Infrastructure;
+using Microsoft.EntityFrameworkCore.Migrations;
+using Microsoft.EntityFrameworkCore.Storage.ValueConversion;
+
+#nullable disable
+
+namespace ClaudeDo.Data.Migrations
+{
+    [DbContext(typeof(ClaudeDoDbContext))]
+    [Migration("20260806111454_AddInteractiveSessionId")]
+    partial class AddInteractiveSessionId
+    {
+        /// <inheritdoc />
+        protected override void BuildTargetModel(ModelBuilder modelBuilder)
+        {
+#pragma warning disable 612, 618
+            modelBuilder.HasAnnotation("ProductVersion", "8.0.11");
+
+            modelBuilder.Entity("ClaudeDo.Data.Models.AppSettingsEntity", b =>
+                {
+                    b.Property<int>("Id")
+                        .HasColumnType("INTEGER")
+                        .HasColumnName("id");
+
+                    b.Property<string>("CentralWorktreeRoot")
+                        .HasColumnType("TEXT")
+                        .HasColumnName("central_worktree_root");
+
+                    b.Property<int>("DailyPrepMaxTasks")
+                        .ValueGeneratedOnAdd()
+                        .HasColumnType("INTEGER")
+                        .HasDefaultValue(5)
+                        .HasColumnName("daily_prep_max_tasks");
+
+                    b.Property<string>("DefaultClaudeInstructions")
+                        .IsRequired()
+                        .ValueGeneratedOnAdd()
+                        .HasColumnType("TEXT")
+                        .HasDefaultValue("")
+                        .HasColumnName("default_claude_instructions");
+
+                    b.Property<int>("DefaultMaxTurns")
+                        .ValueGeneratedOnAdd()
+                        .HasColumnType("INTEGER")
+                        .HasDefaultValue(40)
+                        .HasColumnName("default_max_turns");
+
+                    b.Property<string>("DefaultModel")
+                        .IsRequired()
+                        .ValueGeneratedOnAdd()
+                        .HasColumnType("TEXT")
+                        .HasDefaultValue("sonnet")
+                        .HasColumnName("default_model");
+
+                    b.Property<string>("DefaultPermissionMode")
+                        .IsRequired()
+                        .ValueGeneratedOnAdd()
+                        .HasColumnType("TEXT")
+                        .HasDefaultValue("bypassPermissions")
+                        .HasColumnName("default_permission_mode");
+
+                    b.Property<int>("MaxParallelExecutions")
+                        .ValueGeneratedOnAdd()
+                        .HasColumnType("INTEGER")
+                        .HasDefaultValue(1)
+                        .HasColumnName("max_parallel_executions");
+
+                    b.Property<int>("MaxTurnsCeiling")
+                        .ValueGeneratedOnAdd()
+                        .HasColumnType("INTEGER")
+                        .HasDefaultValue(80)
+                        .HasColumnName("max_turns_ceiling");
+
+                    b.Property<string>("ModelPresets")
+                        .HasColumnType("TEXT")
+                        .HasColumnName("model_presets");
+
+                    b.Property<string>("RepoImportFolders")
+                        .HasColumnType("TEXT")
+                        .HasColumnName("repo_import_folders");
+
+                    b.Property<string>("ReportExcludedPaths")
+                        .HasColumnType("TEXT")
+                        .HasColumnName("report_excluded_paths");
+
+                    b.Property<string>("SessionSkills")
+                        .HasColumnType("TEXT")
+                        .HasColumnName("session_skills");
+
+                    b.Property<int>("StandupWeekday")
+                        .ValueGeneratedOnAdd()
+                        .HasColumnType("INTEGER")
+                        .HasDefaultValue(3)
+                        .HasColumnName("standup_weekday");
+
+                    b.Property<int>("UsageGateFiveHourPct")
+                        .ValueGeneratedOnAdd()
+                        .HasColumnType("INTEGER")
+                        .HasDefaultValue(80)
+                        .HasColumnName("usage_gate_five_hour_pct");
+
+                    b.Property<int>("UsageGateSevenDayPct")
+                        .ValueGeneratedOnAdd()
+                        .HasColumnType("INTEGER")
+                        .HasDefaultValue(90)
+                        .HasColumnName("usage_gate_seven_day_pct");
+
+                    b.Property<int>("UsageThrottleHardPct")
+                        .ValueGeneratedOnAdd()
+                        .HasColumnType("INTEGER")
+                        .HasDefaultValue(65)
+                        .HasColumnName("usage_throttle_hard_pct");
+
+                    b.Property<int>("UsageThrottleSoftPct")
+                        .ValueGeneratedOnAdd()
+                        .HasColumnType("INTEGER")
+                        .HasDefaultValue(50)
+                        .HasColumnName("usage_throttle_soft_pct");
+
+                    b.Property<int>("WorktreeAutoCleanupDays")
+                        .ValueGeneratedOnAdd()
+                        .HasColumnType("INTEGER")
+                        .HasDefaultValue(7)
+                        .HasColumnName("worktree_auto_cleanup_days");
+
+                    b.Property<bool>("WorktreeAutoCleanupEnabled")
+                        .ValueGeneratedOnAdd()
+                        .HasColumnType("INTEGER")
+                        .HasDefaultValue(false)
+                        .HasColumnName("worktree_auto_cleanup_enabled");
+
+                    b.Property<string>("WorktreeStrategy")
+                        .IsRequired()
+                        .ValueGeneratedOnAdd()
+                        .HasColumnType("TEXT")
+                        .HasDefaultValue("sibling")
+                        .HasColumnName("worktree_strategy");
+
+                    b.HasKey("Id");
+
+                    b.ToTable("app_settings", (string)null);
+
+                    b.HasData(
+                        new
+                        {
+                            Id = 1,
+                            DailyPrepMaxTasks = 5,
+                            DefaultClaudeInstructions = "",
+                            DefaultMaxTurns = 40,
+                            DefaultModel = "sonnet",
+                            DefaultPermissionMode = "auto",
+                            MaxParallelExecutions = 1,
+                            MaxTurnsCeiling = 80,
+                            StandupWeekday = 3,
+                            UsageGateFiveHourPct = 80,
+                            UsageGateSevenDayPct = 90,
+                            UsageThrottleHardPct = 65,
+                            UsageThrottleSoftPct = 50,
+                            WorktreeAutoCleanupDays = 7,
+                            WorktreeAutoCleanupEnabled = false,
+                            WorktreeStrategy = "sibling"
+                        });
+                });
+
+            modelBuilder.Entity("ClaudeDo.Data.Models.DailyNoteEntity", b =>
+                {
+                    b.Property<string>("Id")
+                        .HasColumnType("TEXT")
+                        .HasColumnName("id");
+
+                    b.Property<DateTime>("CreatedAt")
+                        .HasColumnType("TEXT")
+                        .HasColumnName("created_at");
+
+                    b.Property<DateOnly>("Date")
+                        .HasColumnType("TEXT")
+                        .HasColumnName("note_date");
+
+                    b.Property<int>("SortOrder")
+                        .HasColumnType("INTEGER")
+                        .HasColumnName("sort_order");
+
+                    b.Property<string>("Text")
+                        .IsRequired()
+                        .HasColumnType("TEXT")
+                        .HasColumnName("text");
+
+                    b.HasKey("Id");
+
+                    b.HasIndex("Date");
+
+                    b.ToTable("daily_notes", (string)null);
+                });
+
+            modelBuilder.Entity("ClaudeDo.Data.Models.ListConfigEntity", b =>
+                {
+                    b.Property<string>("ListId")
+                        .HasColumnType("TEXT")
+                        .HasColumnName("list_id");
+
+                    b.Property<string>("AgentPath")
+                        .HasColumnType("TEXT")
+                        .HasColumnName("agent_path");
+
+                    b.Property<int?>("MaxTurns")
+                        .HasColumnType("INTEGER")
+                        .HasColumnName("max_turns");
+
+                    b.Property<string>("Model")
+                        .HasColumnType("TEXT")
+                        .HasColumnName("model");
+
+                    b.Property<string>("SessionSkills")
+                        .HasColumnType("TEXT")
+                        .HasColumnName("session_skills");
+
+                    b.Property<string>("SystemPrompt")
+                        .HasColumnType("TEXT")
+                        .HasColumnName("system_prompt");
+
+                    b.Property<string>("VerifyCommand")
+                        .HasColumnType("TEXT")
+                        .HasColumnName("verify_command");
+
+                    b.HasKey("ListId");
+
+                    b.ToTable("list_config", (string)null);
+                });
+
+            modelBuilder.Entity("ClaudeDo.Data.Models.ListEntity", b =>
+                {
+                    b.Property<string>("Id")
+                        .HasColumnType("TEXT")
+                        .HasColumnName("id");
+
+                    b.Property<DateTime>("CreatedAt")
+                        .HasColumnType("TEXT")
+                        .HasColumnName("created_at");
+
+                    b.Property<string>("DefaultCommitType")
+                        .IsRequired()
+                        .ValueGeneratedOnAdd()
+                        .HasColumnType("TEXT")
+                        .HasDefaultValue("chore")
+                        .HasColumnName("default_commit_type");
+
+                    b.Property<bool>("IsManual")
+                        .ValueGeneratedOnAdd()
+                        .HasColumnType("INTEGER")
+                        .HasDefaultValue(false)
+                        .HasColumnName("is_manual");
+
+                    b.Property<string>("Name")
+                        .IsRequired()
+                        .HasColumnType("TEXT")
+                        .HasColumnName("name");
+
+                    b.Property<int>("SortOrder")
+                        .ValueGeneratedOnAdd()
+                        .HasColumnType("INTEGER")
+                        .HasDefaultValue(0)
+                        .HasColumnName("sort_order");
+
+                    b.Property<string>("WorkingDir")
+                        .HasColumnType("TEXT")
+                        .HasColumnName("working_dir");
+
+                    b.HasKey("Id");
+
+                    b.HasIndex("SortOrder")
+                        .HasDatabaseName("idx_lists_sort");
+
+                    b.ToTable("lists", (string)null);
+                });
+
+            modelBuilder.Entity("ClaudeDo.Data.Models.PrimeScheduleEntity", b =>
+                {
+                    b.Property<Guid>("Id")
+                        .HasColumnType("TEXT")
+                        .HasColumnName("id");
+
+                    b.Property<DateTimeOffset>("CreatedAt")
+                        .HasColumnType("TEXT")
+                        .HasColumnName("created_at");
+
+                    b.Property<int>("Days")
+                        .ValueGeneratedOnAdd()
+                        .HasColumnType("INTEGER")
+                        .HasDefaultValue(31)
+                        .HasColumnName("days_of_week");
+
+                    b.Property<bool>("Enabled")
+                        .ValueGeneratedOnAdd()
+                        .HasColumnType("INTEGER")
+                        .HasDefaultValue(true)
+                        .HasColumnName("enabled");
+
+                    b.Property<DateTimeOffset?>("LastRunAt")
+                        .HasColumnType("TEXT")
+                        .HasColumnName("last_run_at");
+
+                    b.Property<string>("PromptOverride")
+                        .HasColumnType("TEXT")
+                        .HasColumnName("prompt_override");
+
+                    b.Property<TimeSpan>("TimeOfDay")
+                        .HasColumnType("TEXT")
+                        .HasColumnName("time_of_day");
+
+                    b.HasKey("Id");
+
+                    b.ToTable("prime_schedules", (string)null);
+                });
+
+            modelBuilder.Entity("ClaudeDo.Data.Models.SessionSkillEntity", b =>
+                {
+                    b.Property<string>("Name")
+                        .HasColumnType("TEXT")
+                        .HasColumnName("name");
+
+                    b.Property<DateTimeOffset>("AddedAt")
+                        .HasColumnType("TEXT")
+                        .HasColumnName("added_at");
+
+                    b.Property<string>("Description")
+                        .IsRequired()
+                        .HasColumnType("TEXT")
+                        .HasColumnName("description");
+
+                    b.Property<string>("PinnedRef")
+                        .IsRequired()
+                        .HasColumnType("TEXT")
+                        .HasColumnName("pinned_ref");
+
+                    b.Property<string>("SourceUrl")
+                        .IsRequired()
+                        .HasColumnType("TEXT")
+                        .HasColumnName("source_url");
+
+                    b.Property<string>("Subpath")
+                        .IsRequired()
+                        .HasColumnType("TEXT")
+                        .HasColumnName("subpath");
+
+                    b.HasKey("Name");
+
+                    b.ToTable("session_skills", (string)null);
+                });
+
+            modelBuilder.Entity("ClaudeDo.Data.Models.SubtaskEntity", b =>
+                {
+                    b.Property<string>("Id")
+                        .HasColumnType("TEXT")
+                        .HasColumnName("id");
+
+                    b.Property<bool>("Completed")
+                        .ValueGeneratedOnAdd()
+                        .HasColumnType("INTEGER")
+                        .HasDefaultValue(false)
+                        .HasColumnName("completed");
+
+                    b.Property<DateTime>("CreatedAt")
+                        .HasColumnType("TEXT")
+                        .HasColumnName("created_at");
+
+                    b.Property<int>("OrderNum")
+                        .HasColumnType("INTEGER")
+                        .HasColumnName("order_num");
+
+                    b.Property<string>("TaskId")
+                        .IsRequired()
+                        .HasColumnType("TEXT")
+                        .HasColumnName("task_id");
+
+                    b.Property<string>("Title")
+                        .IsRequired()
+                        .HasColumnType("TEXT")
+                        .HasColumnName("title");
+
+                    b.HasKey("Id");
+
+                    b.HasIndex("TaskId")
+                        .HasDatabaseName("idx_subtasks_task_id");
+
+                    b.ToTable("subtasks", (string)null);
+                });
+
+            modelBuilder.Entity("ClaudeDo.Data.Models.TaskAttachmentEntity", b =>
+                {
+                    b.Property<string>("Id")
+                        .HasColumnType("TEXT")
+                        .HasColumnName("id");
+
+                    b.Property<long>("ByteSize")
+                        .HasColumnType("INTEGER")
+                        .HasColumnName("byte_size");
+
+                    b.Property<DateTime>("CreatedAt")
+                        .HasColumnType("TEXT")
+                        .HasColumnName("created_at");
+
+                    b.Property<string>("FileName")
+                        .IsRequired()
+                        .HasColumnType("TEXT")
+                        .HasColumnName("file_name");
+
+                    b.Property<string>("TaskId")
+                        .IsRequired()
+                        .HasColumnType("TEXT")
+                        .HasColumnName("task_id");
+
+                    b.HasKey("Id");
+
+                    b.HasIndex("TaskId")
+                        .HasDatabaseName("idx_task_attachments_task_id");
+
+                    b.ToTable("task_attachments", (string)null);
+                });
+
+            modelBuilder.Entity("ClaudeDo.Data.Models.TaskEntity", b =>
+                {
+                    b.Property<string>("Id")
+                        .HasColumnType("TEXT")
+                        .HasColumnName("id");
+
+                    b.Property<string>("AgentPath")
+                        .HasColumnType("TEXT")
+                        .HasColumnName("agent_path");
+
+                    b.Property<string>("BlockedByTaskId")
+                        .HasColumnType("TEXT")
+                        .HasColumnName("blocked_by_task_id");
+
+                    b.Property<string>("CommitType")
+                        .IsRequired()
+                        .ValueGeneratedOnAdd()
+                        .HasColumnType("TEXT")
+                        .HasDefaultValue("chore")
+                        .HasColumnName("commit_type");
+
+                    b.Property<DateTime>("CreatedAt")
+                        .HasColumnType("TEXT")
+                        .HasColumnName("created_at");
+
+                    b.Property<string>("CreatedBy")
+                        .HasColumnType("TEXT")
+                        .HasColumnName("created_by");
+
+                    b.Property<string>("Description")
+                        .HasColumnType("TEXT")
+                        .HasColumnName("description");
+
+                    b.Property<DateTime?>("FinishedAt")
+                        .HasColumnType("TEXT")
+                        .HasColumnName("finished_at");
+
+                    b.Property<string>("HandlerBaseCommit")
+                        .HasColumnType("TEXT")
+                        .HasColumnName("handler_base_commit");
+
+                    b.Property<string>("HandlerHeadCommit")
+                        .HasColumnType("TEXT")
+                        .HasColumnName("handler_head_commit");
+
+                    b.Property<string>("InteractiveSessionId")
+                        .HasColumnType("TEXT")
+                        .HasColumnName("interactive_session_id");
+
+                    b.Property<bool>("IsManual")
+                        .ValueGeneratedOnAdd()
+                        .HasColumnType("INTEGER")
+                        .HasDefaultValue(false)
+                        .HasColumnName("is_manual");
+
+                    b.Property<bool>("IsMyDay")
+                        .ValueGeneratedOnAdd()
+                        .HasColumnType("INTEGER")
+                        .HasDefaultValue(false)
+                        .HasColumnName("is_my_day");
+
+                    b.Property<bool>("IsStarred")
+                        .ValueGeneratedOnAdd()
+                        .HasColumnType("INTEGER")
+                        .HasDefaultValue(false)
+                        .HasColumnName("is_starred");
+
+                    b.Property<string>("ListId")
+                        .IsRequired()
+                        .HasColumnType("TEXT")
+                        .HasColumnName("list_id");
+
+                    b.Property<string>("LogPath")
+                        .HasColumnType("TEXT")
+                        .HasColumnName("log_path");
+
+                    b.Property<int?>("MaxTurns")
+                        .HasColumnType("INTEGER")
+                        .HasColumnName("max_turns");
+
+                    b.Property<string>("Model")
+                        .HasColumnType("TEXT")
+                        .HasColumnName("model");
+
+                    b.Property<string>("Notes")
+                        .HasColumnType("TEXT")
+                        .HasColumnName("notes");
+
+                    b.Property<string>("ParentTaskId")
+                        .HasColumnType("TEXT")
+                        .HasColumnName("parent_task_id");
+
+                    b.Property<DateTime?>("PlanningFinalizedAt")
+                        .HasColumnType("TEXT")
+                        .HasColumnName("planning_finalized_at");
+
+                    b.Property<string>("PlanningPhase")
+                        .IsRequired()
+                        .ValueGeneratedOnAdd()
+                        .HasColumnType("TEXT")
+                        .HasDefaultValue("none")
+                        .HasColumnName("planning_phase");
+
+                    b.Property<string>("PlanningSessionId")
+                        .HasColumnType("TEXT")
+                        .HasColumnName("planning_session_id");
+
+                    b.Property<string>("PlanningSessionToken")
+                        .HasColumnType("TEXT")
+                        .HasColumnName("planning_session_token");
+
+                    b.Property<string>("Result")
+                        .HasColumnType("TEXT")
+                        .HasColumnName("result");
+
+                    b.Property<string>("ReviewFeedback")
+                        .HasColumnType("TEXT")
+                        .HasColumnName("review_feedback");
+
+                    b.Property<int>("RoadblockCount")
+                        .ValueGeneratedOnAdd()
+                        .HasColumnType("INTEGER")
+                        .HasDefaultValue(0)
+                        .HasColumnName("roadblock_count");
+
+                    b.Property<DateTime?>("ScheduledFor")
+                        .HasColumnType("TEXT")
+                        .HasColumnName("scheduled_for");
+
+                    b.Property<string>("SessionSkills")
+                        .HasColumnType("TEXT")
+                        .HasColumnName("session_skills");
+
+                    b.Property<int>("SortOrder")
+                        .ValueGeneratedOnAdd()
+                        .HasColumnType("INTEGER")
+                        .HasDefaultValue(0)
+                        .HasColumnName("sort_order");
+
+                    b.Property<DateTime?>("StartedAt")
+                        .HasColumnType("TEXT")
+                        .HasColumnName("started_at");
+
+                    b.Property<string>("Status")
+                        .IsRequired()
+                        .HasColumnType("TEXT")
+                        .HasColumnName("status");
+
+                    b.Property<string>("SystemPrompt")
+                        .HasColumnType("TEXT")
+                        .HasColumnName("system_prompt");
+
+                    b.Property<string>("Title")
+                        .IsRequired()
+                        .HasColumnType("TEXT")
+                        .HasColumnName("title");
+
+                    b.HasKey("Id");
+
+                    b.HasIndex("BlockedByTaskId")
+                        .HasDatabaseName("idx_tasks_blocked_by");
+
+                    b.HasIndex("ListId")
+                        .HasDatabaseName("idx_tasks_list_id");
+
+                    b.HasIndex("ParentTaskId")
+                        .HasDatabaseName("idx_tasks_parent_task_id");
+
+                    b.HasIndex("Status")
+                        .HasDatabaseName("idx_tasks_status");
+
+                    b.HasIndex("ListId", "SortOrder")
+                        .HasDatabaseName("idx_tasks_list_sort");
+
+                    b.ToTable("tasks", (string)null);
+                });
+
+            modelBuilder.Entity("ClaudeDo.Data.Models.TaskRunEntity", b =>
+                {
+                    b.Property<string>("Id")
+                        .HasColumnType("TEXT")
+                        .HasColumnName("id");
+
+                    b.Property<int?>("CacheReadTokens")
+                        .HasColumnType("INTEGER")
+                        .HasColumnName("cache_read_tokens");
+
+                    b.Property<int?>("CacheWriteTokens")
+                        .HasColumnType("INTEGER")
+                        .HasColumnName("cache_write_tokens");
+
+                    b.Property<string>("ErrorMarkdown")
+                        .HasColumnType("TEXT")
+                        .HasColumnName("error_markdown");
+
+                    b.Property<int?>("ExitCode")
+                        .HasColumnType("INTEGER")
+                        .HasColumnName("exit_code");
+
+                    b.Property<DateTime?>("FinishedAt")
+                        .HasColumnType("TEXT")
+                        .HasColumnName("finished_at");
+
+                    b.Property<bool>("IsRetry")
+                        .ValueGeneratedOnAdd()
+                        .HasColumnType("INTEGER")
+                        .HasDefaultValue(false)
+                        .HasColumnName("is_retry");
+
+                    b.Property<string>("LogPath")
+                        .HasColumnType("TEXT")
+                        .HasColumnName("log_path");
+
+                    b.Property<string>("Model")
+                        .HasColumnType("TEXT")
+                        .HasColumnName("model");
+
+                    b.Property<string>("Prompt")
+                        .IsRequired()
+                        .HasColumnType("TEXT")
+                        .HasColumnName("prompt");
+
+                    b.Property<string>("ResultMarkdown")
+                        .HasColumnType("TEXT")
+                        .HasColumnName("result_markdown");
+
+                    b.Property<int>("RunNumber")
+                        .HasColumnType("INTEGER")
+                        .HasColumnName("run_number");
+
+                    b.Property<string>("SessionId")
+                        .HasColumnType("TEXT")
+                        .HasColumnName("session_id");
+
+                    b.Property<DateTime?>("StartedAt")
+                        .HasColumnType("TEXT")
+                        .HasColumnName("started_at");
+
+                    b.Property<string>("StructuredOutputJson")
+                        .HasColumnType("TEXT")
+                        .HasColumnName("structured_output");
+
+                    b.Property<string>("TaskId")
+                        .IsRequired()
+                        .HasColumnType("TEXT")
+                        .HasColumnName("task_id");
+
+                    b.Property<int?>("TokensIn")
+                        .HasColumnType("INTEGER")
+                        .HasColumnName("tokens_in");
+
+                    b.Property<int?>("TokensOut")
+                        .HasColumnType("INTEGER")
+                        .HasColumnName("tokens_out");
+
+                    b.Property<int?>("TurnCount")
+                        .HasColumnType("INTEGER")
+                        .HasColumnName("turn_count");
+
+                    b.HasKey("Id");
+
+                    b.HasIndex("TaskId")
+                        .HasDatabaseName("idx_task_runs_task_id");
+
+                    b.ToTable("task_runs", (string)null);
+                });
+
+            modelBuilder.Entity("ClaudeDo.Data.Models.WeekReportEntity", b =>
+                {
+                    b.Property<string>("Id")
+                        .HasColumnType("TEXT")
+                        .HasColumnName("id");
+
+                    b.Property<DateOnly>("EndDate")
+                        .HasColumnType("TEXT")
+                        .HasColumnName("end_date");
+
+                    b.Property<DateTime>("GeneratedAt")
+                        .HasColumnType("TEXT")
+                        .HasColumnName("generated_at");
+
+                    b.Property<string>("Markdown")
+                        .IsRequired()
+                        .HasColumnType("TEXT")
+                        .HasColumnName("markdown");
+
+                    b.Property<DateOnly>("StartDate")
+                        .HasColumnType("TEXT")
+                        .HasColumnName("start_date");
+
+                    b.HasKey("Id");
+
+                    b.HasIndex("StartDate", "EndDate")
+                        .IsUnique();
+
+                    b.ToTable("week_reports", (string)null);
+                });
+
+            modelBuilder.Entity("ClaudeDo.Data.Models.WorktreeEntity", b =>
+                {
+                    b.Property<string>("TaskId")
+                        .HasColumnType("TEXT")
+                        .HasColumnName("task_id");
+
+                    b.Property<string>("BaseCommit")
+                        .IsRequired()
+                        .HasColumnType("TEXT")
+                        .HasColumnName("base_commit");
+
+                    b.Property<string>("BranchName")
+                        .IsRequired()
+                        .HasColumnType("TEXT")
+                        .HasColumnName("branch_name");
+
+                    b.Property<DateTime>("CreatedAt")
+                        .HasColumnType("TEXT")
+                        .HasColumnName("created_at");
+
+                    b.Property<string>("DiffStat")
+                        .HasColumnType("TEXT")
+                        .HasColumnName("diff_stat");
+
+                    b.Property<string>("HeadCommit")
+                        .HasColumnType("TEXT")
+                        .HasColumnName("head_commit");
+
+                    b.Property<string>("MergeCommit")
+                        .HasColumnType("TEXT")
+                        .HasColumnName("merge_commit");
+
+                    b.Property<string>("Path")
+                        .IsRequired()
+                        .HasColumnType("TEXT")
+                        .HasColumnName("path");
+
+                    b.Property<string>("State")
+                        .IsRequired()
+                        .ValueGeneratedOnAdd()
+                        .HasColumnType("TEXT")
+                        .HasDefaultValue("active")
+                        .HasColumnName("state");
+
+                    b.HasKey("TaskId");
+
+                    b.ToTable("worktrees", (string)null);
+                });
+
+            modelBuilder.Entity("ClaudeDo.Data.Models.ListConfigEntity", b =>
+                {
+                    b.HasOne("ClaudeDo.Data.Models.ListEntity", "List")
+                        .WithOne("Config")
+                        .HasForeignKey("ClaudeDo.Data.Models.ListConfigEntity", "ListId")
+                        .OnDelete(DeleteBehavior.Cascade)
+                        .IsRequired();
+
+                    b.Navigation("List");
+                });
+
+            modelBuilder.Entity("ClaudeDo.Data.Models.SubtaskEntity", b =>
+                {
+                    b.HasOne("ClaudeDo.Data.Models.TaskEntity", "Task")
+                        .WithMany("Subtasks")
+                        .HasForeignKey("TaskId")
+                        .OnDelete(DeleteBehavior.Cascade)
+                        .IsRequired();
+
+                    b.Navigation("Task");
+                });
+
+            modelBuilder.Entity("ClaudeDo.Data.Models.TaskAttachmentEntity", b =>
+                {
+                    b.HasOne("ClaudeDo.Data.Models.TaskEntity", "Task")
+                        .WithMany()
+                        .HasForeignKey("TaskId")
+                        .OnDelete(DeleteBehavior.Cascade)
+                        .IsRequired();
+
+                    b.Navigation("Task");
+                });
+
+            modelBuilder.Entity("ClaudeDo.Data.Models.TaskEntity", b =>
+                {
+                    b.HasOne("ClaudeDo.Data.Models.TaskEntity", null)
+                        .WithMany()
+                        .HasForeignKey("BlockedByTaskId")
+                        .OnDelete(DeleteBehavior.SetNull);
+
+                    b.HasOne("ClaudeDo.Data.Models.ListEntity", "List")
+                        .WithMany("Tasks")
+                        .HasForeignKey("ListId")
+                        .OnDelete(DeleteBehavior.Cascade)
+                        .IsRequired();
+
+                    b.HasOne("ClaudeDo.Data.Models.TaskEntity", "Parent")
+                        .WithMany("Children")
+                        .HasForeignKey("ParentTaskId")
+                        .OnDelete(DeleteBehavior.Restrict);
+
+                    b.Navigation("List");
+
+                    b.Navigation("Parent");
+                });
+
+            modelBuilder.Entity("ClaudeDo.Data.Models.TaskRunEntity", b =>
+                {
+                    b.HasOne("ClaudeDo.Data.Models.TaskEntity", "Task")
+                        .WithMany("Runs")
+                        .HasForeignKey("TaskId")
+                        .OnDelete(DeleteBehavior.Cascade)
+                        .IsRequired();
+
+                    b.Navigation("Task");
+                });
+
+            modelBuilder.Entity("ClaudeDo.Data.Models.WorktreeEntity", b =>
+                {
+                    b.HasOne("ClaudeDo.Data.Models.TaskEntity", "Task")
+                        .WithOne("Worktree")
+                        .HasForeignKey("ClaudeDo.Data.Models.WorktreeEntity", "TaskId")
+                        .OnDelete(DeleteBehavior.Cascade)
+                        .IsRequired();
+
+                    b.Navigation("Task");
+                });
+
+            modelBuilder.Entity("ClaudeDo.Data.Models.ListEntity", b =>
+                {
+                    b.Navigation("Config");
+
+                    b.Navigation("Tasks");
+                });
+
+            modelBuilder.Entity("ClaudeDo.Data.Models.TaskEntity", b =>
+                {
+                    b.Navigation("Children");
+
+                    b.Navigation("Runs");
+
+                    b.Navigation("Subtasks");
+
+                    b.Navigation("Worktree");
+                });
+#pragma warning restore 612, 618
+        }
+    }
+}

src/ClaudeDo.Data/Migrations/20260806111454_AddInteractiveSessionId.cs

@@ -0,0 +1,28 @@
+using Microsoft.EntityFrameworkCore.Migrations;
+
+#nullable disable
+
+namespace ClaudeDo.Data.Migrations
+{
+    /// <inheritdoc />
+    public partial class AddInteractiveSessionId : Migration
+    {
+        /// <inheritdoc />
+        protected override void Up(MigrationBuilder migrationBuilder)
+        {
+            migrationBuilder.AddColumn<string>(
+                name: "interactive_session_id",
+                table: "tasks",
+                type: "TEXT",
+                nullable: true);
+        }
+
+        /// <inheritdoc />
+        protected override void Down(MigrationBuilder migrationBuilder)
+        {
+            migrationBuilder.DropColumn(
+                name: "interactive_session_id",
+                table: "tasks");
+        }
+    }
+}

src/ClaudeDo.Data/Migrations/ClaudeDoDbContextModelSnapshot.cs

@@ -463,6 +463,10 @@ namespace ClaudeDo.Data.Migrations
                         .HasColumnType("TEXT")
                         .HasColumnName("handler_head_commit");
 
+                    b.Property<string>("InteractiveSessionId")
+                        .HasColumnType("TEXT")
+                        .HasColumnName("interactive_session_id");
+
                     b.Property<bool>("IsManual")
                         .ValueGeneratedOnAdd()
                         .HasColumnType("INTEGER")

src/ClaudeDo.Data/Models/TaskEntity.cs

@@ -60,6 +60,12 @@ public sealed class TaskEntity
     public string? HandlerBaseCommit { get; set; }
     public string? HandlerHeadCommit { get; set; }
 
+    // The claude session id an embedded ConPTY interactive task session is (or was last)
+    // running under -- generated up front and persisted before launch so a closed/aborted
+    // session can be resumed even if the process never got past startup. Cleared implicitly
+    // whenever the task's worktree is recreated (a fresh worktree has nothing to resume into).
+    public string? InteractiveSessionId { get; set; }
+
     public string? ParentTaskId { get; set; }
     public string? PlanningSessionId { get; set; }
     public string? PlanningSessionToken { get; set; }

src/ClaudeDo.Data/Repositories/TaskRepository.cs

@@ -402,6 +402,19 @@ public sealed class TaskRepository
                 .SetProperty(t => t.HandlerHeadCommit, headCommit), ct);
     }
 
+    // Persists the claude session id a fresh embedded ConPTY interactive task session will run
+    // under, written BEFORE launch so a closed/aborted session still leaves a resumable id.
+    public async Task SetInteractiveSessionIdAsync(
+        string taskId,
+        string? sessionId,
+        CancellationToken ct = default)
+    {
+        await _context.Tasks
+            .Where(t => t.Id == taskId)
+            .ExecuteUpdateAsync(s => s
+                .SetProperty(t => t.InteractiveSessionId, sessionId), ct);
+    }
+
     public async Task<TaskEntity?> FindByPlanningTokenAsync(
         string token,
         CancellationToken ct = default)

src/ClaudeDo.Worker/Runner/InteractiveLaunchSpecService.cs

@@ -104,12 +104,30 @@ public sealed class InteractiveLaunchSpecService : IInteractiveLaunchSpecService
         // The model itself is deliberately NOT forced here — the user can still switch it in the TUI.
         var effort = EffortFor(globalSettings, task.Model ?? listConfig?.Model);
 
-        // Resume an existing session as-is; for a fresh session, seed the interactive TUI with
-        // the task's brief (title + description) via a file, never as a positional CLI argument --
-        // see BuildFreshTaskArgsAsync for why.
-        var args = run?.SessionId is { Length: > 0 } sessionId
-            ? WithEffort(WindowsTerminalLauncher.BuildResumeArgs(sessionId), effort)
-            : await BuildFreshTaskArgsAsync(task, effort, ct);
+        // Resume this task's own last interactive conversation when it has one -- it takes
+        // precedence over the latest autonomous run's session, since an interactive session is a
+        // distinct conversation from an autonomous run even against the same worktree. Fall back
+        // to the autonomous run's session so opening a task interactively for the first time still
+        // picks up prior context. Neither survives a freshly (re)created worktree (isFreshWorktree
+        // already forced `run` to null above).
+        var resumeSessionId = isFreshWorktree ? null : task.InteractiveSessionId ?? run?.SessionId;
+
+        // For a fresh session, seed the interactive TUI with the task's brief (title +
+        // description) via a file, never as a positional CLI argument -- see
+        // BuildFreshTaskArgsAsync for why. The session id claude will run under is generated and
+        // persisted HERE, before launch, so a closed/aborted session -- even one that never got
+        // past startup -- still leaves an id the next open can resume.
+        IReadOnlyList<string> args;
+        if (resumeSessionId is { Length: > 0 })
+        {
+            args = WithEffort(WindowsTerminalLauncher.BuildResumeArgs(resumeSessionId), effort);
+        }
+        else
+        {
+            var sessionId = Guid.NewGuid().ToString();
+            await new TaskRepository(ctx).SetInteractiveSessionIdAsync(taskId, sessionId, ct);
+            args = await BuildFreshTaskArgsAsync(task, effort, sessionId, ct);
+        }
 
         // Same run environment variable ClaudeProcess sets for every headless run: the
         // AskUser MCP tool call and wait_for_task_change cap at 60s unless raised, and lifting
@@ -445,11 +463,15 @@ public sealed class InteractiveLaunchSpecService : IInteractiveLaunchSpecService
     // Read; --effort (single-value) must sit directly before the positional kickoff so the
     // preceding variadic --add-dir doesn't swallow the kickoff as another directory.
     // No brief (task has neither a title nor a description) -> no positional arg at all.
-    private static async Task<IReadOnlyList<string>> BuildFreshTaskArgsAsync(TaskEntity task, string effort, CancellationToken ct)
+    // `--session-id` pre-assigns the claude session id the caller already persisted (see
+    // BuildForTaskAsync) so this fresh conversation is resumable from its very first turn --
+    // it's a single-value flag, so it may sit directly before the positional kickoff.
+    private static async Task<IReadOnlyList<string>> BuildFreshTaskArgsAsync(
+        TaskEntity task, string effort, string sessionId, CancellationToken ct)
     {
         var brief = BuildTaskBrief(task);
         if (string.IsNullOrEmpty(brief))
-            return new[] { "--effort", effort };
+            return new[] { "--effort", effort, "--session-id", sessionId };
 
         var sessionDir = Path.Combine(Paths.AppDataRoot(), "task-sessions", task.Id);
         Directory.CreateDirectory(sessionDir);
@@ -460,6 +482,7 @@ public sealed class InteractiveLaunchSpecService : IInteractiveLaunchSpecService
         {
             "--add-dir", sessionDir,
             "--effort", effort,
+            "--session-id", sessionId,
             $"Read the file {briefPath} first. It contains the task you must work on. " +
             "After reading it, begin the session as your instructions describe.",
         };

src/ClaudeDo.Worker/Runner/Interfaces/IInteractiveLaunchSpecService.cs

@@ -17,9 +17,12 @@ public interface IInteractiveLaunchSpecService
     /// Throws KeyNotFoundException if the task doesn't exist, InvalidOperationException
     /// if it's Running/Queued. If the task has no usable worktree yet, one is created on
     /// demand (same mechanism as an autonomous run) provided the task's list has a working
-    /// directory pointing at a git repo -- otherwise throws InvalidOperationException. A task
-    /// that has never run, or whose worktree was just created fresh, gets a fresh-start spec
-    /// (no --resume); an existing worktree with a persisted SessionId gets --resume.</summary>
+    /// directory pointing at a git repo -- otherwise throws InvalidOperationException. Resumes
+    /// (--resume) this task's own last interactive session (TaskEntity.InteractiveSessionId) if
+    /// it has one, else the latest autonomous run's session; a task that has never run either
+    /// way, or whose worktree was just created fresh, gets a fresh-start spec instead -- pre-
+    /// assigned a new session id via --session-id and persisted to InteractiveSessionId before
+    /// launch, so a closed/aborted session can be resumed next time.</summary>
     Task<LaunchSpec> BuildForTaskAsync(string taskId, CancellationToken ct);
 
     /// <summary>Builds a LaunchSpec for an ad-hoc interactive session in an arbitrary directory --

tests/ClaudeDo.Worker.Tests/Runner/InteractiveLaunchSpecServiceTests.cs

@@ -194,7 +194,7 @@ public sealed class InteractiveLaunchSpecServiceTests : IDisposable
         Assert.Equal(wtRow.Path, spec.Cwd);
         Assert.Equal(_claudeStubPath, spec.Exe);
 
-        var (_, briefPath, kickoff) = ParseFreshTaskArgs(spec);
+        var (_, briefPath, kickoff, _) = ParseFreshTaskArgs(spec);
         Assert.Contains(briefPath, kickoff); // fresh session points claude at the brief file, not a raw prompt
         Assert.Equal("T", File.ReadAllText(briefPath)); // brief file holds the task title
     }
@@ -272,10 +272,14 @@ public sealed class InteractiveLaunchSpecServiceTests : IDisposable
         var svc = BuildService();
         var spec = await svc.BuildForTaskAsync(taskId, CancellationToken.None);
 
-        var (_, briefPath, kickoff) = ParseFreshTaskArgs(spec); // fresh: no --resume, brief file holds the title
+        var (_, briefPath, kickoff, sessionId) = ParseFreshTaskArgs(spec); // fresh: no --resume, brief file holds the title
         Assert.Contains(briefPath, kickoff);
         Assert.Equal("T", File.ReadAllText(briefPath));
         Assert.Equal(_worktreeDir, spec.Cwd);
+
+        // The generated session id is persisted BEFORE this call returns, so a closed/aborted
+        // session still leaves a resumable id.
+        Assert.Equal(sessionId, await ReadInteractiveSessionIdAsync(taskId));
     }
 
     [Fact]
@@ -290,9 +294,73 @@ public sealed class InteractiveLaunchSpecServiceTests : IDisposable
         var svc = BuildService();
         var spec = await svc.BuildForTaskAsync(taskId, CancellationToken.None);
 
-        var (_, briefPath, kickoff) = ParseFreshTaskArgs(spec); // fresh: brief file holds the title
+        var (_, briefPath, kickoff, sessionId) = ParseFreshTaskArgs(spec); // fresh: brief file holds the title
         Assert.Contains(briefPath, kickoff);
         Assert.Equal("T", File.ReadAllText(briefPath));
+        Assert.Equal(sessionId, await ReadInteractiveSessionIdAsync(taskId));
+    }
+
+    [Fact]
+    public async Task BuildForTaskAsync_ExistingInteractiveSessionId_TakesPrecedenceOverRunSessionId()
+    {
+        var listId = await SeedListAsync();
+        var taskId = Guid.NewGuid().ToString();
+        await SeedTaskAsync(taskId, listId, TaskStatus.Idle);
+        await SeedWorktreeAsync(taskId, WorktreeState.Active);
+        await SeedRunAsync(taskId, "autonomous-run-session");
+        using (var ctx = _db.CreateContext())
+        {
+            await new TaskRepository(ctx).SetInteractiveSessionIdAsync(taskId, "interactive-session-1");
+        }
+
+        var svc = BuildService();
+        var spec = await svc.BuildForTaskAsync(taskId, CancellationToken.None);
+
+        Assert.Equal(new[] { "--resume", "interactive-session-1" }, ArgsAfterEffort(spec));
+    }
+
+    [Fact]
+    public async Task BuildForTaskAsync_ReopeningInteractiveSession_ResumesItsOwnPriorSessionId()
+    {
+        var listId = await SeedListAsync();
+        var taskId = Guid.NewGuid().ToString();
+        await SeedTaskAsync(taskId, listId, TaskStatus.Idle);
+        await SeedWorktreeAsync(taskId, WorktreeState.Active);
+        // No autonomous run at all -- only a prior interactive session for this task.
+
+        var svc = BuildService();
+        var firstSpec = await svc.BuildForTaskAsync(taskId, CancellationToken.None);
+        var (_, _, _, firstSessionId) = ParseFreshTaskArgs(firstSpec);
+
+        // Reopen (e.g. the pane was closed/aborted) -- must resume the SAME session id, not
+        // start a new conversation.
+        var secondSpec = await svc.BuildForTaskAsync(taskId, CancellationToken.None);
+
+        Assert.Equal(new[] { "--resume", firstSessionId }, ArgsAfterEffort(secondSpec));
+    }
+
+    [Fact]
+    public async Task BuildForTaskAsync_FreshlyRecreatedWorktree_IgnoresAndOverwritesStaleInteractiveSessionId()
+    {
+        if (!GitAvailable) { Assert.True(true, "git not available -- skipping"); return; }
+
+        var repo = CreateRepo();
+        var listId = await SeedListAsync(workingDir: repo.RepoDir);
+        var taskId = Guid.NewGuid().ToString();
+        await SeedTaskAsync(taskId, listId, TaskStatus.Idle);
+        // No worktree row seeded -- BuildForTaskAsync will create one fresh.
+        using (var ctx = _db.CreateContext())
+        {
+            await new TaskRepository(ctx).SetInteractiveSessionIdAsync(taskId, "stale-interactive-session");
+        }
+
+        var svc = BuildService();
+        var spec = await svc.BuildForTaskAsync(taskId, CancellationToken.None);
+
+        // Fresh-start, not a resume of the stale id.
+        var (_, _, _, newSessionId) = ParseFreshTaskArgs(spec);
+        Assert.NotEqual("stale-interactive-session", newSessionId);
+        Assert.Equal(newSessionId, await ReadInteractiveSessionIdAsync(taskId));
     }
 
     [Fact]
@@ -312,7 +380,7 @@ public sealed class InteractiveLaunchSpecServiceTests : IDisposable
         var svc = BuildService();
         var spec = await svc.BuildForTaskAsync(taskId, CancellationToken.None);
 
-        var (_, briefPath, kickoff) = ParseFreshTaskArgs(spec);
+        var (_, briefPath, kickoff, _) = ParseFreshTaskArgs(spec);
         Assert.Contains(briefPath, kickoff);
         Assert.Equal("T\n\nDo the thing", File.ReadAllText(briefPath));
     }
@@ -336,7 +404,7 @@ public sealed class InteractiveLaunchSpecServiceTests : IDisposable
         var svc = BuildService();
         var spec = await svc.BuildForTaskAsync(taskId, CancellationToken.None);
 
-        var (_, briefPath, kickoff) = ParseFreshTaskArgs(spec);
+        var (_, briefPath, kickoff, _) = ParseFreshTaskArgs(spec);
         Assert.Contains(briefPath, kickoff);
         Assert.DoesNotContain('\n', kickoff);
 
@@ -364,7 +432,10 @@ public sealed class InteractiveLaunchSpecServiceTests : IDisposable
         var svc = BuildService();
         var spec = await svc.BuildForTaskAsync(taskId, CancellationToken.None);
 
-        Assert.Empty(ArgsAfterEffort(spec)); // no brief -> no --add-dir, no positional arg
+        // no brief -> no --add-dir, no positional arg -- but a session id is still pre-assigned
+        var rest = ArgsAfterEffort(spec);
+        Assert.Equal("--session-id", rest[0]);
+        Assert.Equal(rest[1], await ReadInteractiveSessionIdAsync(taskId));
     }
 
     [Fact]
@@ -427,22 +498,31 @@ public sealed class InteractiveLaunchSpecServiceTests : IDisposable
     }
 
     /// A fresh (never-resumed) task with a title/description produces
-    /// `--add-dir <sessionDir> --effort <level> <kickoff>` -- the brief travels via the file at
-    /// <sessionDir>/brief.md, never as a raw CLI argument. Asserts that exact shape and returns
-    /// (sessionDir, briefPath, kickoff) for the test's own checks. Cleanup happens via
-    /// `_seededTaskIds` in Dispose (the session dir is keyed by task id).
-    private static (string SessionDir, string BriefPath, string Kickoff) ParseFreshTaskArgs(LaunchSpec spec)
+    /// `--add-dir <sessionDir> --effort <level> --session-id <guid> <kickoff>` -- the brief
+    /// travels via the file at <sessionDir>/brief.md, never as a raw CLI argument. Asserts that
+    /// exact shape and returns (sessionDir, briefPath, kickoff, sessionId) for the test's own
+    /// checks. Cleanup happens via `_seededTaskIds` in Dispose (the session dir is keyed by task id).
+    private static (string SessionDir, string BriefPath, string Kickoff, string SessionId) ParseFreshTaskArgs(LaunchSpec spec)
     {
         var args = spec.Args.ToList();
-        Assert.Equal(5, args.Count);
+        Assert.Equal(7, args.Count);
         Assert.Equal("--add-dir", args[0]);
         var sessionDir = args[1];
         Assert.Equal("--effort", args[2]);
         Assert.Equal(ModelPresets.For(ModelPresets.Defaults, ModelRegistry.DefaultAlias).Effort, args[3]);
-        var kickoff = args[4];
+        Assert.Equal("--session-id", args[4]);
+        var sessionId = args[5];
+        var kickoff = args[6];
 
         var briefPath = Path.Combine(sessionDir, "brief.md");
-        return (sessionDir, briefPath, kickoff);
+        return (sessionDir, briefPath, kickoff, sessionId);
+    }
+
+    private async Task<string?> ReadInteractiveSessionIdAsync(string taskId)
+    {
+        using var ctx = _db.CreateContext();
+        var task = await new TaskRepository(ctx).GetByIdAsync(taskId);
+        return task!.InteractiveSessionId;
     }
 
     private readonly List<string> _mergeHelperSessionDirs = new();