massive-value · massive-value · Jun 14, 2026 · Jun 14, 2026 · Jun 14, 2026 · Jun 14, 2026
diff --git a/CHANGELOG.md b/CHANGELOG.md
@@ -7,6 +7,42 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
 
 ## [Unreleased]
 
+## [0.3.4] - 2026-06-14
+
+### Fixed
+
+- **In-app update no longer reports "Updated successfully" while staying on
+  the old version (#131).** Three independent defects, each sufficient to
+  cause the symptom, were found and fixed:
+  1. **`update.ps1` failed to parse under Windows PowerShell 5.1.** The script
+     was UTF-8 without a BOM and contained em-dashes (`—`). The updater
+     launches Windows PowerShell 5.1, which reads a BOM-less `.ps1` as the
+     ANSI codepage (Windows-1252), not UTF-8. The em-dash inside the
+     `"Tray exe missing at $trayExe — cannot restart"` string literal
+     misdecoded — its trailing byte read as a closing quote — so the whole
+     script failed to parse and silently never ran. `update.ps1` and
+     `install.ps1` are now pure ASCII, with regression guards. (PowerShell 7,
+     used in development, defaults to UTF-8 and masked this.)
+  2. **False success reporting.** The success sentinel was pre-written before
+     the updater launched and only cleared on explicit failure. It is now
+     written by `update.ps1` only *after* a successful extraction, the tray
+     waits for the updater's heartbeat before quitting (reporting an honest
+     failure if it never starts), and the success banner is shown only when
+     the running version actually matches the installed target.
+  3. **Stale `dist-info` left the wrong version reported.** Overlay extraction
+     (`Expand-Archive -Force`) never deletes orphaned files, so the previous
+     version's `plaud_tools-*.dist-info` survived next to the new one and
+     `importlib.metadata` resolved the old version. `update.ps1` now prunes
+     stale `dist-info` after extracting.
+- The updater also now launches the helper with `CREATE_BREAKAWAY_FROM_JOB`
+  (graceful fallback when the job forbids it) so it survives the tray exiting.
+
+> **Note:** because the in-app updater runs the *currently installed*
+> `update.ps1`, users on **v0.3.3 or earlier cannot reach v0.3.4 via the in-app
+> button** — the broken script parse-fails the same way. Reinstall with the
+> `install.ps1` one-liner (now ASCII-fixed) to land on v0.3.4; updates work
+> in-app from v0.3.4 onward.
+
 ## [0.3.3] - 2026-06-13
 
 ### Fixed
@@ -1225,7 +1261,8 @@ For full detail see the v0.1.20–v0.1.22 sections below. Headline items:
   `scripts/plaud_entry.py` wrapper mirrors the existing
   `plaud_mcp_entry.py` / `plaud_tray_entry.py` pattern.
 
-[Unreleased]: https://github.com/massive-value/plaud-tools/compare/v0.3.3...HEAD
+[Unreleased]: https://github.com/massive-value/plaud-tools/compare/v0.3.4...HEAD
+[0.3.4]: https://github.com/massive-value/plaud-tools/compare/v0.3.3...v0.3.4
 [0.3.3]: https://github.com/massive-value/plaud-tools/compare/v0.3.2...v0.3.3
 [0.3.2]: https://github.com/massive-value/plaud-tools/compare/v0.3.1...v0.3.2
 [0.3.1]: https://github.com/massive-value/plaud-tools/compare/v0.3.0...v0.3.1

diff --git a/pyproject.toml b/pyproject.toml
@@ -4,7 +4,7 @@ build-backend = "setuptools.build_meta"
 
 [project]
 name = "plaud-tools"
-version = "0.3.3"
+version = "0.3.4"
 description = "Python rewrite for Plaud CLI and MCP workflows."
 readme = "README.md"
 requires-python = ">=3.11"

diff --git a/scripts/install.ps1 b/scripts/install.ps1
@@ -4,8 +4,8 @@
 #   irm https://raw.githubusercontent.com/massive-value/plaud-tools/main/scripts/install.ps1 | iex
 #
 # Options:
-#   -Force   — remove any existing install (after shutting down tray + MCP) and reinstall.
-#   -Repair  — alias for -Force; use when files are missing or quarantined.
+#   -Force   - remove any existing install (after shutting down tray + MCP) and reinstall.
+#   -Repair  - alias for -Force; use when files are missing or quarantined.
 #
 # Example:
 #   irm .../install.ps1 | iex                      # normal install
@@ -118,7 +118,7 @@ function Get-ZipExtractDestination {
             $prefix = $roots[0] + '/'
             $hasChildren = $zip.Entries | Where-Object { $_.FullName -ne $prefix -and $_.FullName.StartsWith($prefix) }
             if ($hasChildren) {
-                # Extract to parent — the folder inside the zip becomes $InstallDir.
+                # Extract to parent - the folder inside the zip becomes $InstallDir.
                 return (Split-Path $InstallDir -Parent)
             }
         }
@@ -145,9 +145,9 @@ try {
         throw "Could not find PlaudTools.zip in the latest release assets. Check https://github.com/massive-value/plaud-tools/releases/latest"
     }
 
-    Write-Host "    Latest: v$latestVersion — PlaudTools.zip ($([math]::Round($asset.size / 1MB, 1)) MB)"
+    Write-Host "    Latest: v$latestVersion - PlaudTools.zip ($([math]::Round($asset.size / 1MB, 1)) MB)"
 
-    # Strip any pre-release suffix (e.g. "0.3.0-rc1" → "0.3.0") before casting
+    # Strip any pre-release suffix (e.g. "0.3.0-rc1" -> "0.3.0") before casting
     # to [version] so that numeric comparison is always used and a pre-release tag
     # is never ranked above or equal to the same numeric release.
     function Get-NumericVersion {
@@ -181,7 +181,7 @@ try {
             # -Force/-Repair: shut down running processes then wipe the install dir.
             $switchName = if ($Repair) { '-Repair' } else { '-Force' }
             Write-Host ''
-            Write-Host "$switchName specified — shutting down PlaudTools processes..." -ForegroundColor Yellow
+            Write-Host "$switchName specified - shutting down PlaudTools processes..." -ForegroundColor Yellow
 
             # Gracefully stop any running tray process.
             $trayProcs = Get-Process -Name 'PlaudTools' -ErrorAction SilentlyContinue | Where-Object {
@@ -217,7 +217,7 @@ try {
     # Broken/partial install: directory exists but exe is missing (e.g. Defender quarantine).
     if (Test-Path $installDir) {
         Write-Host ''
-        Write-Host 'Found an incomplete installation (directory present, exe missing) — cleaning up...' -ForegroundColor Yellow
+        Write-Host 'Found an incomplete installation (directory present, exe missing) - cleaning up...' -ForegroundColor Yellow
         Remove-Item $installDir -Recurse -Force
     }
 
@@ -233,7 +233,7 @@ try {
     # from v0.3.0 onward.
     #
     # Verification is FAIL CLOSED (#113): a hash mismatch aborts the install, and
-    # so does an absent SHA256SUMS asset — an absent asset means a malformed
+    # so does an absent SHA256SUMS asset - an absent asset means a malformed
     # release or a tampered asset list, and the download cannot be trusted.
     $sumsAsset = $release.assets | Where-Object { $_.name -eq 'SHA256SUMS' } | Select-Object -First 1
     if (-not $sumsAsset) {
@@ -249,7 +249,7 @@ try {
         $actualHash   = (Get-FileHash -Path $zipTemp -Algorithm SHA256).Hash.ToUpper()
         if ($actualHash -ne $expectedHash) {
             throw (
-                "SHA256 mismatch — the downloaded zip may be corrupt or tampered.`n" +
+                "SHA256 mismatch - the downloaded zip may be corrupt or tampered.`n" +
                 "  Expected: $expectedHash`n" +
                 "  Actual:   $actualHash`n" +
                 'Please retry; if the mismatch persists report it at https://github.com/massive-value/plaud-tools/issues'
@@ -307,7 +307,7 @@ try {
     $completionsDir = Join-Path $installDir 'completions'
     $ps1File = Join-Path $completionsDir 'plaud-tools.ps1'
     if (Test-Path $ps1File) {
-        # Regex anchored to the install dir — only our sourcing lines are touched
+        # Regex anchored to the install dir - only our sourcing lines are touched
         $escapedDir  = [regex]::Escape($completionsDir)
         $stalePattern = "^\. `"$($escapedDir -replace '\\\\','[/\\\\]')[/\\\\]plaud[^`"]*\.ps1`""
         $sourceLine  = ". `"$ps1File`""
@@ -345,7 +345,7 @@ try {
     # 4c. Register autostart in HKCU Run key (idempotent)
     #
     # The value name MUST match plaud_tools.tray.setup._AUTOSTART_NAME ("Plaud
-    # Tools", with a space) — that is what the tray reads in _autostart_enabled
+    # Tools", with a space) - that is what the tray reads in _autostart_enabled
     # and writes in _set_autostart.  Earlier revisions of this script wrote
     # "PlaudTools" (no space); we strip that stale name on every run so users
     # who upgraded through the buggy version do not end up with two Run keys

diff --git a/src/plaud_tools/ps1_templates.py b/src/plaud_tools/ps1_templates.py
@@ -69,6 +69,7 @@ def render_update_ps1(
     zip_path: str,
     extract_dir: str,
     dispatcher_path: str | None = None,
+    new_version: str | None = None,
 ) -> str:
     """Return a PS1 dispatcher that calls the bundled update.ps1 with the given args.
 
@@ -91,6 +92,14 @@ def render_update_ps1(
         Absolute path to the dispatcher PS1 itself. Passed to update.ps1 as
         ``-DispatcherPath`` so update.ps1 can delete it after a successful
         run. Optional for backwards compatibility with older callers.
+    new_version:
+        The version being installed (e.g. ``"0.3.3"``). Passed to update.ps1
+        as ``-NewVersion`` so it can (a) prune stale ``plaud_tools-*.dist-info``
+        directories left behind by the overlay extraction — otherwise
+        ``importlib.metadata.version`` resolves the OLD version and the tray
+        keeps reporting the pre-update version — and (b) write the
+        ``plaud_just_updated.txt`` success sentinel only AFTER a successful
+        extraction. Optional for backwards compatibility with older callers.
     """
     scripts = scripts_dir()
     ps1 = scripts / "update.ps1"
@@ -108,6 +117,9 @@ def render_update_ps1(
     if dispatcher_path:
         safe_dispatcher = _ps_escape(dispatcher_path)
         line += f" -DispatcherPath '{safe_dispatcher}'"
+    if new_version:
+        safe_version = _ps_escape(new_version)
+        line += f" -NewVersion '{safe_version}'"
     return line + "\n"
 
 

diff --git a/src/plaud_tools/scripts/update.ps1 b/src/plaud_tools/scripts/update.ps1
@@ -17,7 +17,7 @@
     The tray reads this on next launch and surfaces the failure to the user.
 
     The tray is restarted in a `finally` block, so the user is never stranded
-    without a tray icon — even when the update itself fails.
+    without a tray icon - even when the update itself fails.
 
 .PARAMETER TrayPid
     PID of the running PlaudTools.exe (tray app) to wait for.
@@ -35,8 +35,14 @@
 .PARAMETER DispatcherPath
     Optional path to the %TEMP% dispatcher PS1 that invoked this script. Deleted
     after a successful run so %TEMP% does not accumulate stale .ps1 files. The
-    bundled update.ps1 itself is NEVER deleted — earlier versions self-deleted
+    bundled update.ps1 itself is NEVER deleted - earlier versions self-deleted
     it, which broke subsequent in-app updates.
+
+.PARAMETER NewVersion
+    The version being installed (e.g. "0.3.3"). Used to (a) prune stale
+    plaud_tools-*.dist-info directories left behind by the overlay extraction
+    so importlib.metadata resolves the NEW version, and (b) write the
+    plaud_just_updated.txt success sentinel only AFTER a successful extraction.
 #>
 param(
     [Parameter(Mandatory)]
@@ -53,14 +59,16 @@ param(
 
     [string]$DispatcherPath = "",
 
-    [string]$SentinelPath = ""
+    [string]$SentinelPath = "",
+
+    [string]$NewVersion = ""
 )
 
 Set-StrictMode -Off
 $ErrorActionPreference = 'Continue'
 
 # ---------------------------------------------------------------------------
-# Diagnostics — transcript log + structured failure sentinel
+# Diagnostics - transcript log + structured failure sentinel
 # ---------------------------------------------------------------------------
 
 $logPath        = Join-Path $env:TEMP "plaud_update_$TrayPid.log"
@@ -94,7 +102,7 @@ function Write-FailureSentinel {
         } | ConvertTo-Json -Compress
         Set-Content -Path $failSentinel -Value $payload -Encoding UTF8 -ErrorAction Stop
     } catch {
-        # Best effort — the reason is still in the transcript log.
+        # Best effort - the reason is still in the transcript log.
     }
     # A failed update must not leave the success sentinel behind, otherwise the
     # restarted (still-old) tray would falsely announce a successful upgrade.
@@ -139,19 +147,43 @@ function Get-ZipExtractDestination {
     }
 }
 
+# ---------------------------------------------------------------------------
+# Remove orphaned plaud_tools-*.dist-info directories left behind by the
+# overlay extraction (Expand-Archive -Force overwrites matching paths but never
+# deletes files absent from the zip). If a previous version's dist-info
+# survives next to the new one, importlib.metadata.version("plaud-tools")
+# resolves the OLD version and the tray keeps reporting the pre-update version
+# (and re-offering the same "update available"). Keep only $NewVersion's
+# dist-info. No-op when $NewVersion is empty (older callers).
+# ---------------------------------------------------------------------------
+
+function Remove-StaleDistInfo {
+    param([string]$InstallDir, [string]$NewVersion)
+
+    if (-not $NewVersion) { return }
+    $keep = "plaud_tools-$NewVersion.dist-info"
+    $stale = Get-ChildItem -Path $InstallDir -Recurse -Directory `
+        -Filter 'plaud_tools-*.dist-info' -ErrorAction SilentlyContinue |
+        Where-Object { $_.Name -ne $keep }
+    foreach ($d in $stale) {
+        Write-Host "Removing stale dist-info: $($d.FullName)"
+        Remove-Item -LiteralPath $d.FullName -Recurse -Force -ErrorAction SilentlyContinue
+    }
+}
+
 # ---------------------------------------------------------------------------
 # Stop ALL processes whose Path is under $InstallDir (plaud-mcp, ffmpeg, any
 # other child processes), and confirm they stay dead. Returns $true when no
 # scoped process has been alive for $StableMs milliseconds. Returns $false if
 # a supervisor keeps respawning processes after $MaxAttempts attempts.
 #
-# This is the bug the v0.2.0 → 0.2.1 update path hit: when Claude Desktop
+# This is the bug the v0.2.0 -> 0.2.1 update path hit: when Claude Desktop
 # launches plaud-mcp, killing the process just causes Claude to relaunch it
 # almost immediately, and the respawned exe keeps mcp\_internal\*.dll locked,
 # causing Expand-Archive to throw and the script to bail.
 #
 # Using path-based discovery (rather than name-based) also catches ffmpeg and
-# any other child processes that plaud-mcp may have spawned — Stop-Process on
+# any other child processes that plaud-mcp may have spawned - Stop-Process on
 # the parent does NOT kill children on Windows.
 # ---------------------------------------------------------------------------
 
@@ -173,7 +205,7 @@ function Stop-PlaudMcpScoped {
     for ($attempt = 1; $attempt -le $MaxAttempts; $attempt++) {
         $procs = & $findProcs
         if (-not $procs) {
-            # Nothing alive — wait $StableMs to make sure nobody respawns it.
+            # Nothing alive - wait $StableMs to make sure nobody respawns it.
             Start-Sleep -Milliseconds $StableMs
             if (-not (& $findProcs)) {
                 Write-Host "All install-dir processes confirmed stopped (attempt $attempt)"
@@ -246,7 +278,7 @@ try {
     Write-Host "Extraction complete"
 
     # 4. Cleanup: remove the zip and the %TEMP% dispatcher. The bundled
-    #    update.ps1 (this very script) is NOT deleted — earlier versions
+    #    update.ps1 (this very script) is NOT deleted - earlier versions
     #    self-deleted via $MyInvocation.MyCommand.Path, which broke subsequent
     #    in-app updates because the script vanished after the first successful
     #    upgrade.
@@ -255,6 +287,19 @@ try {
         Remove-Item $DispatcherPath -ErrorAction SilentlyContinue
     }
 
+    # 5. Prune stale dist-info so the restarted tray resolves the NEW version.
+    Remove-StaleDistInfo -InstallDir $InstallDir -NewVersion $NewVersion
+
+    # 6. Write the success sentinel ONLY now that extraction has actually
+    #    succeeded. (Earlier the tray pre-wrote this before launching the
+    #    updater, so a silently-failed update - e.g. the updater process being
+    #    killed before it ran - still left the sentinel behind and the old tray
+    #    falsely announced success. The tray additionally verifies the running
+    #    version matches before showing the success banner.)
+    if ($NewVersion) {
+        Set-Content -Path $successSentinel -Value $NewVersion -Encoding UTF8 -ErrorAction SilentlyContinue
+    }
+
     Write-Host "Update succeeded"
 }
 catch {
@@ -270,7 +315,7 @@ catch {
 finally {
     # 5. Always restart the tray so the user is not stranded after a failed
     #    update. If the new tray bundle is in place, we get the new version;
-    #    if extraction failed, we get the old one back — better than nothing.
+    #    if extraction failed, we get the old one back - better than nothing.
     $trayExe = Join-Path $InstallDir 'PlaudTools.exe'
     if (Test-Path $trayExe) {
         try {
@@ -280,7 +325,7 @@ finally {
             Write-Host "Could not restart tray: $($_.Exception.Message)"
         }
     } else {
-        Write-Host "Tray exe missing at $trayExe — cannot restart"
+        Write-Host "Tray exe missing at $trayExe - cannot restart"
     }
 
     try { Stop-Transcript | Out-Null } catch {}

diff --git a/src/plaud_tools/tray/app.py b/src/plaud_tools/tray/app.py
@@ -409,22 +409,43 @@ def _show_update_failure(r: str = reason, lp: str = log_path) -> None:
             except Exception:
                 logging.warning("Could not read update failure sentinel", exc_info=True)
 
-        # If relaunched after an in-app update, open HomeWindow with a success message.
+        # If relaunched after an in-app update, open HomeWindow with a success
+        # message — but ONLY if the running version actually matches the version
+        # the update claimed to install. The sentinel proves the updater ran its
+        # success path; this guard additionally proves the new bits are actually
+        # the ones now executing. Without it, a silently-failed or partially
+        # applied update (stale dist-info, killed updater, etc.) would falsely
+        # announce success while the tray is still on the old version.
         sentinel = Path(tempfile.gettempdir()) / "plaud_just_updated.txt"
         if sentinel.exists():
             try:
                 updated_to = sentinel.read_text(encoding="utf-8").strip()
                 sentinel.unlink(missing_ok=True)
+                version_matches = updated_to == APP_VERSION
+                if not version_matches:
+                    logging.warning(
+                        "Update sentinel claims v%s but running version is v%s — "
+                        "the update did not take effect; suppressing success banner.",
+                        updated_to,
+                        APP_VERSION,
+                    )
                 if self._session and self._home_win:
 
-                    def _show_update_success(v: str = updated_to) -> None:
+                    def _show_update_status(v: str = updated_to, ok: bool = version_matches) -> None:
                         # Re-check for mypy: outer guard `if self._home_win` doesn't
                         # narrow inside a nested def captured by a closure.
                         if self._home_win is not None:
                             self._home_win.show()
-                            self._home_win._set_status(f"Updated to v{v} successfully.", ok=True)
-
-                    root.after(500, _show_update_success)
+                            if ok:
+                                self._home_win._set_status(f"Updated to v{v} successfully.", ok=True)
+                            else:
+                                self._home_win._set_status(
+                                    f"Update to v{v} did not complete — still on "
+                                    f"v{APP_VERSION}. See logs for details.",
+                                    ok=False,
+                                )
+
+                    root.after(500, _show_update_status)
             except Exception:
                 logging.warning("Could not read update sentinel", exc_info=True)