edmund-release-and-operate

name

edmund-release-and-operate

description

Load when cutting or debugging an Edmund release, or operating the shipped app. Triggers: version bump (Info.plist CFBundleShortVersionString / CFBundleVersion), tagging vX.Y.Z, CHANGELOG.md release sections, release.yml / release.sh / build-app.sh, appcast.xml or Sparkle update failures ("improperly signed", update never offered), sign_update / EdDSA keys / SPARKLE_ED_PRIVATE_KEY / RELEASE_TOKEN, create-dmg or DMG naming problems, Gatekeeper "damaged" reports, launching the built app, reading ~/.edmund/logs, crash reports (edmd-*.ips), or roadmap/priority questions.

Edmund — release & operate

Date-stamped 2026-07-05. Verified against .github/workflows/release.yml, scripts/release.sh, scripts/build-app.sh, scripts/changelog-to-html.py, appcast.xml, Info.plist, CHANGELOG.md, docs/ARCHITECTURE.md §8/§13, and the Settings/CrashReporter sources. Where a doc and a script disagree, the script is the truth; disagreements are flagged inline.

House rule: releases happen only when the maintainer explicitly asks. Never tag, push, create a release, or merge on your own initiative — see edmund-change-control. Everything in §1–§4 below is a runbook for when the maintainer says "cut a release", not a standing instruction.

When NOT to use this skill

You actually need	Go to
Build/test commands, stale-build cures, launch mechanics in depth	edmund-build-and-env
Editing invariants, render pipeline, TextKit 2 rules	edmund-architecture-contract, textkit2-appkit-reference
Debugging a bug in the app itself	edmund-debugging-playbook, edmund-live-repro-and-diagnostics
Past incidents and why the sharp edges below exist	edmund-failure-archaeology
Debug flags / launch arguments	edmund-config-and-flags
Branch/commit/PR etiquette, what needs maintainer sign-off	edmund-change-control
Pre-merge QA method	edmund-validation-and-qa
README/website/positioning copy	edmund-docs-and-writing, edmund-external-positioning

---

1. Release flow — CI path (the normal one)

Ship via a tag; CI does the rest. In order:

1. Bump versions in Info.plist — both keys:
   • CFBundleShortVersionString — marketing version, e.g. 0.1.3
   • CFBundleVersion — build number, monotonic integer (0.1.3 = 4)
2. Add a ## [x.y.z] section to CHANGELOG.md — format is load-bearing, see §2. The version MUST match Info.plist exactly.
3. Merge to main and push (via the normal PR flow).
4. Tag and push the tag:

   git tag vX.Y.Z && git push origin vX.Y.Z
   

5. CI (.github/workflows/release.yml, trigger push: tags: 'v*', runner macos-14, job release / "Build & publish") runs the steps below.
6. Afterwards, verify per §4 post-flight.

release.yml step anatomy (actual step names)

Step	What it does	Sharp edge
actions/checkout@v5	fetch-depth: 0, token: ${{ secrets.RELEASE_TOKEN }}	The PAT must be on this step — see §3.4
maxim-lobanov/setup-xcode@v1	latest-stable Xcode
Cache .build	SPM cache keyed on Package.resolved
Build app bundle	./scripts/build-app.sh — release build, bundle assembly, Sparkle embed, bundle sealing	§3.2
actions/setup-node@v4	pins Node 20	create-dmg 8.x needs Node ≥ 20
Install create-dmg	npm install --global create-dmg (sindresorhus/create-dmg, not Homebrew's)	§3.5
Create DMG	reads VERSION from Info.plist, create-dmg build/Edmund.app build/ || true, renames "Edmund <v>.dmg" → Edmund-<v>.dmg, fails loudly if no dmg	§3.5
Sign archive (EdDSA)	finds sign_update in .build, key on stdin via --ed-key-file -, exports ED_SIG and LENGTH	§3.1
Create GitHub Release	awk-extracts the CHANGELOG section → gh release create "v${VERSION}" build/Edmund-${VERSION}.dmg --title "Edmund ${VERSION}" --notes-file … --latest	§2
Update appcast.xml	builds the new <item> (HTML <description> via scripts/changelog-to-html.py), inserts it before </channel>, commits as github-actions[bot], git push origin HEAD:main	§3.4

Local path (scripts/release.sh)

Mirrors CI: build-app.sh → create-dmg (+ rename) → EdDSA sign → update appcast.xml locally → gh release create. Two differences:

• Signing: with SPARKLE_ED_PRIVATE_KEY in the env it uses the stdin path (CI-style); otherwise sign_update pulls the key from the login keychain (put there by Sparkle's generate_keys) with no flag at all.
• The appcast commit/push is left to you. The script ends with the exact commands: git add appcast.xml && git commit -m 'Release <v>' && git push.

Prereqs for the local path: gh auth status authenticated, npm create-dmg installed, swift build has run at least once (so sign_update exists under .build).

Stale doc: misc/how-to-release.md still says the artifact is a zip ("signs the zip", "Zip it to build/Edmund-1.0.zip"). That predates the DMG switch. The truth is DMG throughout — per release.yml, release.sh, and ARCHITECTURE §13. Trust the scripts, and fix that doc when touching it.

---

2. CHANGELOG format contract (release notes are machine-extracted)

Both release.yml and release.sh extract the GitHub Release body with:

awk "BEGIN{p=0} /^## \[${VERSION}\]/{p=1;next} p && /^## \[/{exit} p{print}" CHANGELOG.md

So the section header must start at column 0 as ## [x.y.z] — literally ## [0.1.3] — 2026-07-04 in house style (em dash + ISO date after the bracket is fine; the match only requires the ^## \[x.y.z\] prefix). Extraction runs until the next ^## [ line. If nothing matches, the release body falls back to "See CHANGELOG for details." — a silent-ish failure, so get the header right. (Version dots are unescaped in the regex; harmless in practice, don't rely on it.)

The Sparkle update-dialog notes come from the same section via scripts/changelog-to-html.py <version>, a deliberately tiny converter that only understands Keep-a-Changelog shapes:

• ### Added / ### Changed / ### Fixed → <h3> — use ###, not ##. The 0.1.2 appcast item literally shows <p>## Changed</p> because the section used ## subheads at release time; the converter passed them through as paragraphs.
• - / * bullets → <ul><li>; indented continuation lines fold into the previous bullet.
• `code` and **bold** are converted. Markdown links are NOT — [docs](docs/foo.md) appears literally in the update dialog (see the 0.1.2 item). Keep appcast-facing notes link-free or accept the raw brackets.
• Blank lines and --- are skipped; anything else becomes a <p>.
• Missing section → empty output → the <description> is simply omitted.

House format (verified from CHANGELOG.md): Keep a Changelog 1.1.0 + SemVer, newest first, sections separated by ---.

---

3. The sharp edges (each one killed or nearly killed a real release)

3.1 sign_update -s is FATAL — key goes on stdin

Sparkle deprecated -s <key>; for newly generated keys it prints a deprecation warning and exits 1 ("no longer supported"). This killed the first 0.1.0 release. The only correct invocation with a key-in-hand:

echo "$SPARKLE_ED_PRIVATE_KEY" | sign_update --ed-key-file - <dmg>

Both release.yml and release.sh do exactly this. Never "simplify" it back to -s. Output format: sparkle:edSignature="<sig>" length="<n>" — the scripts grep those two attributes out for the appcast item.

3.2 Bundle sealing (the "improperly signed" update failure)

At install time Sparkle re-validates the update's Apple code signature (SUUpdateValidator), independent of the EdDSA signature. A bundle that is code-signed but not sealed (no _CodeSignature/CodeResources) fails that check and every update dies with "The update is improperly signed and could not be validated" — which is exactly what broke the v0.1.0 → 0.1.1 update when the old script signed only the bare binary.

build-app.sh therefore signs inside-out and in a very deliberate order:

1. codesign --force --deep --sign - Sparkle.framework (nested XPC helpers must be signed before macOS will launch them),
2. codesign --force --deep --sign - --identifier "com.i7t5.edmd" on the whole .app while its root holds only Contents/ — codesign refuses to seal a bundle with extra items at the root,
3. copy the SwiftMath resource bundle to the .app root after sealing (its generated Bundle.module looks at Bundle.main.bundleURL; without it the app crashes on the first LaTeX render).

Consequence: codesign --verify (CLI) and --strict will complain about that one unsealed root item. That is expected and fine — Sparkle's actual check is non-strict (SecStaticCodeCheckValidityWithErrors with kSecCSCheckAllArchitectures) and tolerates it; verified end-to-end against that API. Do not "fix" the verify warning by moving the SwiftMath bundle or re-signing after the copy.

3.3 Keypair discipline

One EdDSA keypair, three places, all of which must agree:

Place	Used by
Info.plist SUPublicEDKey (0XdLbbuO…)	Every shipped app, to verify updates
Maintainer's login keychain	release.sh local signing (no flag)
GitHub secret SPARKLE_ED_PRIVATE_KEY	CI signing

If the signing key and SUPublicEDKey diverge, everything looks fine — the DMG signs without error — but every user's update fails signature verification. Sanity check when in doubt: sign_update --verify <dmg> <sig> against the Info.plist public key.

3.4 Appcast push to protected main — RELEASE_TOKEN

The workflow's last step commits appcast.xml and pushes to main, which requires the test status check. The default GITHUB_TOKEN / github-actions[bot] is not an admin, so that push is rejected with GH006 … protected branch hook declined. Branch protection has enforce_admins: false, so an admin's push bypasses the check — hence the fine-grained admin PAT in the RELEASE_TOKEN secret (Contents: read/write), set as the token: on the checkout step, not on the push. That placement matters: actions/checkout persists an http.<host>.extraheader credential that overrides inline-URL credentials, so rewriting the push URL would keep pushing with the bot token anyway.

RELEASE_TOKEN expires 2027-06-27. Rotate it before then or every release fails at the appcast push while the GitHub Release itself succeeds (a confusing half-shipped state — see §4 post-flight).

3.5 create-dmg quirks

• It's the npm package create-dmg (sindresorhus), installed via npm install --global create-dmg. Homebrew's create-dmg is a different tool with an incompatible CLI. Requires Node ≥ 20 (CI pins it).
• It exits 2 when it can't Developer-ID-sign/notarize the image (Edmund ships ad-hoc) but still produces the .dmg. Both scripts run it with || true and then verify the file exists, failing loudly only if no dmg was produced. Don't remove the || true; don't trust the exit code.
• Output is named "Edmund <version>.dmg" — with a space. Both scripts rename to Edmund-<version>.dmg (hyphen), which is the name the appcast enclosure URL expects. If a rename is skipped, the release asset URL 404s for every updater.

---

4. Pre-flight and post-flight

Pre-flight (distilled from misc/before-you-release.md — read it too)

• swift test green on main, not just the branch; git status clean.
• No debug flags / launch args left on (repro drivers, verbose tracing — see edmund-config-and-flags, ARCHITECTURE §8).
• Visual sanity: build and screencapture the editor in light and dark mode; click through everything the CHANGELOG claims ("fixed X" → actually reproduce X and confirm).
• CHANGELOG.md has ## [x.y.z] — YYYY-MM-DD for this release and the version matches Info.plist (CFBundleShortVersionString); ### subheads, not ## (§2).
• CFBundleVersion bumped (monotonic int).
• RELEASE_TOKEN not expired (2027-06-27).
• Local path only: gh auth status ok; keychain key matches SUPublicEDKey (§3.3).

Post-flight

• GitHub Release vX.Y.Z exists with the right notes and the Edmund-<v>.dmg asset (hyphenated name).
• appcast.xml on main got the new <item> — with <description>, correct sparkle:version (= CFBundleVersion) and enclosure URL.
• Nothing to do for user prompts: Sparkle checks roughly daily; existing users see the update within ~24 h. Don't panic if it isn't instant.

If the Release exists but the appcast commit is missing, the release half-shipped (usually §3.4). Fix the token, then add the <item> manually or re-run the job.

---

5. Gatekeeper story (why users see "damaged")

Edmund is ad-hoc signed, not notarized (no $99/yr Developer ID). First launch of a downloaded copy trips Gatekeeper with the "app is damaged" dialog. This is expected; the app is fine. The README documents both workarounds (verified, README ~line 53):

• xattr -dr com.apple.quarantine /Applications/Edmund.app, or
• right-click → Open.

Known upgrade path (open/candidate, not scheduled): Developer ID certificate

• notarization would remove the prompt entirely and also clean up the non-strict-sealing compromise in §3.2. Don't promise it in user-facing text.

---

6. Operating the app

Launching

open Edmund.app foregrounds a running instance instead of relaunching — you'll stare at old code. And never pkill -x edmd blindly: the maintainer's own Edmund session may be running (the Mach-O is edmd for both). Check first (pgrep -x edmd), kill only PIDs you started, or launch the binary directly: build/Edmund.app/Contents/MacOS/edmd file.md &. Full launch / stale-build / screencapture mechanics: edmund-build-and-env.

Logs — ~/.edmund/logs/edmund-YYYY-MM-DD.log

• One file per day, human-readable lines tagged LEVEL [category] (categories: app, document, io, render, compose, selection, lazy, callout, edit — grep by concern).
• Controlled by Settings ▸ Advanced ▸ Diagnostics ("Save diagnostic logs"). The toggle defaults OFF (AppSettings.diagnosticLogging defaults false) — i.e. opt-in in the shipped app, despite Log.swift's header comment calling it "always-on (opt-out)"; the code is the truth. (The UserDefaults keys are named settings.general.* for legacy reasons; the UI lives in Advanced.)
• Retention picker ("Clear logs after:") next to the toggle; a separate "Verbose editor tracing" opt-in gates keystroke-level trace lines — leave off except during repros (edmund-live-repro-and-diagnostics).
• Release builds write info and up; DEBUG builds also write debug.
• Logs may contain document text; they never leave the machine.

Crash reports — ~/Library/Logs/DiagnosticReports/edmd-*.ips

• macOS names crash reports after the Mach-O executable: look for edmd-<timestamp>.ips, not "Edmund-…".
• Uploading is opt-in and currently INERT. The Settings toggle is commented out in Sources/edmd/Settings/AdvancedSettingsView.swift ("dormant until the receiving server exists"), and CrashReporter.reportingEndpoint is a placeholder (https://REPLACE-ME.invalid/crash). Nothing is ever sent in shipped builds. Don't tell users crash reporting exists; don't uncomment the toggle without a real server. Code: Sources/EdmundCore/Diagnostics/CrashReporter.swift.
• Reading works only because Edmund is not sandboxed; adopting App Sandbox would force a MetricKit rewrite (noted in CrashReporter's header).
• Triage of a user's .ips: it's JSON — a one-line metadata header, then the report body. Look at exception (type/signal), faultingThread, and walk that thread's frames for images named edmd or Sparkle. Ad-hoc builds ship no dSYM, so expect addresses rather than symbol names for app frames; correlate with ~/.edmund/logs from the same timestamp instead. .ips files embed the user's home path and device model — treat as mildly personal data.

Update mechanics (user side)

• SUFeedURL = https://raw.githubusercontent.com/I7T5/Edmund/main/appcast.xml — the raw-GitHub URL of the checked-in appcast; committing to main is publishing.
• SUEnableAutomaticChecks is true; no custom interval is set, so Sparkle uses its default ~24 h cadence (plus a check on launch).
• Sparkle downloads the DMG enclosure, verifies EdDSA against SUPublicEDKey, mounts the DMG, re-validates the Apple code signature (§3.2), installs.

---

7. Versioning & appcast conventions

Thing	Convention	Current (2026-07-05)
Git tag	vX.Y.Z	v0.1.3 pending its tag; last released 0.1.2
CFBundleShortVersionString	SemVer marketing version	0.1.3
CFBundleVersion	monotonic integer, +1 per release	4
CHANGELOG	Keep a Changelog 1.1.0, ## [x.y.z] — YYYY-MM-DD, ### subheads, --- separators	—

appcast.xml (checked into repo root): RSS 2.0 with the sparkle: namespace. One <channel> (title/link/description/language) containing one <item> per release. Items are inserted before </channel>, so the file reads oldest → newest; Sparkle doesn't care about order — it picks by version. Per item:

<item>
    <title>Edmund 0.1.2</title>
    <pubDate>Fri, 03 Jul 2026 19:03:59 +0000</pubDate>
    <description><![CDATA[ …HTML from changelog-to-html.py… ]]></description>
    <enclosure url="https://github.com/I7T5/Edmund/releases/download/v0.1.2/Edmund-0.1.2.dmg"
               sparkle:version="3"                <!-- CFBundleVersion -->
               sparkle:shortVersionString="0.1.2" <!-- marketing version -->
               sparkle:edSignature="…"
               length="7608991"
               type="application/x-apple-diskimage"/>
</item>

<description> is optional (omitted when the CHANGELOG section is missing).

---

8. Roadmap context (for release-content judgment)

• Edmund is in beta (0.1.x line, first public release 0.1.0 on 2026-06-27). Small, frequent releases.
• v0.2.0 goal: "Polished editing experience" (misc/backlog.md § Now).
• Priority ordering: Marketing = Bugs >= UI/UX > Features — when deciding what makes a release, bug fixes and polish beat new features.
• Long-range plan (v1.0 = onboarding + full GFM + extensions groundwork): docs/ROADMAP.md; working backlog with per-bug detail: misc/backlog.md.

---

Provenance and maintenance

Written 2026-07-05 from direct reads of: .github/workflows/release.yml, scripts/release.sh, scripts/build-app.sh, scripts/changelog-to-html.py, appcast.xml, CHANGELOG.md, Info.plist, README.md, docs/ARCHITECTURE.md (§8, §13), misc/how-to-release.md, misc/before-you-release.md, docs/ROADMAP.md, misc/backlog.md, Sources/EdmundCore/Diagnostics/CrashReporter.swift, Sources/EdmundCore/Diagnostics/Log.swift, Sources/edmd/Settings/AdvancedSettingsView.swift, Sources/edmd/Settings/AppSettings.swift.

Known stale docs at time of writing: misc/how-to-release.md (zip vs DMG, §1); Log.swift header ("always-on (opt-out)" vs the actual default-off toggle, §6). Minor oddity, deliberate: build-app.sh signs with --identifier "com.i7t5.edmd" while the bundle id is com.i7t5.edmund.

Re-verify when any of these change: release.yml step names or secrets, build-app.sh signing order, the CHANGELOG header format (the awk regex in two places must match it), SUFeedURL, RELEASE_TOKEN rotation (hard deadline 2027-06-27), notarization status, or the crash-report server going live (which un-inerts §6's crash uploading and this skill's wording).