diff --git a/CHANGELOG.md b/CHANGELOG.md
index 643c1feaf..bc24684d6 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -6,6 +6,44 @@ Format based on [Keep a Changelog](https://keepachangelog.com/en/1.1.0/).
 
 ## [Unreleased]
 
+## [2.27.0] - 2026-03-17
+
+### Added
+- HTML report generator with progression index across milestones
+- Crash recovery for parallel orchestrator — persisted state with PID liveness detection
+- Headless orchestration skill with supervised mode
+- Verification enforcement gate for milestone completion
+- `git.manage_gitignore` preference to opt out of automatic `.gitignore` changes
+
+### Changed
+- Encapsulated auto.ts state into AutoSession class (cleaner session lifecycle)
+- Extracted 7 focused modules from auto.ts (auto-worktree-sync, resource staleness, stale escape)
+- TUI dashboard cleanup, dedup, and feature improvements
+- Reordered visualizer tabs and HTML report sections into logical groupings
+
+### Fixed
+- Single ENTER now correctly submits slash command argument autocomplete
+- Web search loop broken with consecutive duplicate guard
+- Transient network errors retried before model fallback
+- Parallel worker PID tracking, spawn-status race, and exit persistence
+- `/gsd discuss` now recommends next undiscussed slice
+- Roadmap parser allows suffix text after `## Slices` heading
+- User's model choice no longer overwritten when API key is temporarily unavailable
+- Reassess-roadmap skip loop broken by preventing re-persistence of evicted keys
+- LSP command resolution and ENOENT crash on Windows/MSYS
+- Dispatch plan-slice when task plan files are missing
+- Reduced CPU usage on long auto-mode sessions
+- Orphan-prone child processes reaped across session churn
+- Symlinked skill directories resolved in `always_use_skills` and preferences
+- Replan-slice infinite loop and non-standard `finish_reason` crash
+- Skip slice plan commit when `commit_docs` is false
+- Context-pressure monitor wired to send wrap-up signal at 70%
+- Missing STATE.md in fresh worktree no longer deadlocks pre-dispatch health gate
+- Stale runtime unit files for completed milestones cleaned on startup
+- Broken install detection with Windows symlink fallback
+- Auto-restart headless mode on crash with exponential backoff
+- Generic type preserved on `resolveModelId` through resolution
+
 ## [2.26.0] - 2026-03-17
 
 ### Added
@@ -982,7 +1020,8 @@ Format based on [Keep a Changelog](https://keepachangelog.com/en/1.1.0/).
 ### Changed
 - License updated to MIT
 
-[Unreleased]: https://github.com/gsd-build/gsd-2/compare/v2.26.0...HEAD
+[Unreleased]: https://github.com/gsd-build/gsd-2/compare/v2.27.0...HEAD
+[2.27.0]: https://github.com/gsd-build/gsd-2/compare/v2.26.0...v2.27.0
 [2.26.0]: https://github.com/gsd-build/gsd-2/compare/v2.25.0...v2.26.0
 [2.25.0]: https://github.com/gsd-build/gsd-2/releases/tag/v2.25.0
 [2.24.0]: https://github.com/gsd-build/gsd-2/compare/v2.23.0...v2.24.0