Replace Sentry with Datadog monitoring (dd-sdk-ios)

.claude/skills/release/SKILL.md

@@ -1,6 +1,6 @@
 ---
 name: release
-description: Cut and publish a Blurt release (build, sign, notarize, staple, DMG, Sentry, GitHub). Use when the user asks to ship/release a new version. User-invoked only — it has real side effects (notarization, git tags, GitHub release, Sentry release).
+description: Cut and publish a Blurt release (build, sign, notarize, staple, DMG, Datadog, GitHub). Use when the user asks to ship/release a new version. User-invoked only — it has real side effects (notarization, git tags, GitHub release, Datadog dSYM upload).
 disable-model-invocation: true
 ---
 
@@ -12,9 +12,9 @@ the target version with the user before publishing** — publishing is hard to u
 ## Preconditions (verify first)
 
 - Clean working tree on an up-to-date `main` (releases ship from `main`).
-- `sentry-cli` **authenticated** — `sentry-cli login` session or `SENTRY_AUTH_TOKEN`
-  in the env. `release-build.sh` preflight fails fast otherwise. The Sentry org is
-  pinned as the **slug** (`alex-kroman`), not the numeric ID, or sentry-cli warns.
+- (Optional) `DATADOG_API_KEY` in the env for dSYM upload — needs Node/`npx`
+  (datadog-ci). `DATADOG_SITE` defaults to `datadoghq.com` (US1). If unset, the
+  build skips symbol upload with a warning rather than failing.
 - Notary profile `blurt-notary` exists (`xcrun notarytool store-credentials`).
 - Developer ID signing identity present in the keychain.
 
@@ -24,11 +24,11 @@ the target version with the user before publishing** — publishing is hard to u
    and build number in `App/Blurt/project.yml`, regenerates the project, and
    opens a PR (versions land on `main` via PR — `main` is branch-protected).
 2. **Build + sign + notarize** — `scripts/release-build.sh` does the whole Apple
-   path: `xcodebuild` Release → sign nested code **including embedded
-   frameworks** (`Sentry.framework` must get `--options runtime --timestamp`, or
-   notarization rejects it) → notarize → staple → DMG → verify. It also uploads
-   the dSYM to Sentry and creates/finalizes the matching Sentry release
-   (`dev.alex.blurt@<version>+<build>`).
+   path: `xcodebuild` Release → sign nested code **including any embedded
+   frameworks** (each must get `--options runtime --timestamp`, or notarization
+   rejects it) → notarize → staple → DMG → verify. If `DATADOG_API_KEY` is set it
+   also uploads the dSYM to Datadog (via `npx @datadog/datadog-ci`) so crashes
+   symbolicate.
 3. **Publish** — `scripts/release-publish.sh` creates the GitHub release and
    uploads `Blurt.dmg` (the README's download link points at
    `releases/latest/download/Blurt.dmg`).
@@ -41,7 +41,8 @@ the target version with the user before publishing** — publishing is hard to u
 - Notarization rejects any nested mach-o/framework lacking a **secure
   timestamp**; the build re-signs frameworks for this reason — don't remove that.
 - After a release, verify the DMG mounts, the app is stapled
-  (`xcrun stapler validate`), and the Sentry release shows the dSYM.
+  (`xcrun stapler validate`), and — if `DATADOG_API_KEY` was set — Datadog shows
+  the uploaded dSYM.
 - The post-build install step copies to `/Applications` (TCC needs a stable path);
   don't redirect it to DerivedData/`/tmp`.
 

.github/workflows/codeql.yml

@@ -69,7 +69,7 @@ jobs:
         with:
           persist-credentials: false
 
-      # Cache the resolved SwiftPM checkouts so we don't re-clone sentry-cocoa's
+      # Cache the resolved SwiftPM checkouts so we don't re-clone the SDKs'
       # full git history on every run. Keyed on the pinned Package.resolved, so a
       # dependency bump busts the cache. restore-keys lets an older cache seed a
       # partial hit when the pins change.

.mcp.json

@@ -1,9 +1,5 @@
 {
   "mcpServers": {
-    "sentry": {
-      "type": "http",
-      "url": "https://mcp.sentry.dev/mcp"
-    },
     "assemblyai-docs": {
       "type": "http",
       "url": "https://mcp.assemblyai.com/docs"

App/Blurt/Blurt.xcodeproj/project.pbxproj

@@ -161,6 +161,7 @@
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+		6179B457E48877787CE028DA /* DatadogCrashReporting in Frameworks */ = {isa = PBXBuildFile; productRef = 45CD7152E18BFEE0F598216D /* DatadogCrashReporting */; };
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@@ -205,6 +206,7 @@
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+		82FCEE1383634F9B88976992 /* DatadogLogs in Frameworks */ = {isa = PBXBuildFile; productRef = 056BF2B5954A44C3AEEC6DD2 /* DatadogLogs */; };
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@@ -229,6 +231,7 @@
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 		8FE4B9B139BB9557FBC5589B /* OverlayWindowController.swift in Sources */ = {isa = PBXBuildFile; fileRef = A27D7F43295DE2A81EFFDDBC /* OverlayWindowController.swift */; };
+		9108B9B80FE4395A4D6D4F2C /* Monitoring.swift in Sources */ = {isa = PBXBuildFile; fileRef = B48B1FA4FF13F4A4B56BD27D /* Monitoring.swift */; };
 		91C1257866F6E2D4EE65BD09 /* WindowAccessor.swift in Sources */ = {isa = PBXBuildFile; fileRef = 6B2312DE4BC0F4F070830AD7 /* WindowAccessor.swift */; };
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@@ -354,7 +357,7 @@
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-		D6DFF322638007525EBA02B2 /* Sentry in Frameworks */ = {isa = PBXBuildFile; productRef = 39EB6BB06E04EA9CD2CDC3BA /* Sentry */; };
+		D6DFF322638007525EBA02B2 /* DatadogCore in Frameworks */ = {isa = PBXBuildFile; productRef = A0E6571699034CB1C08CB0C9 /* DatadogCore */; };
 		D750C1BF16502EEC92182ECD /* PermissionsStepView.swift in Sources */ = {isa = PBXBuildFile; fileRef = E8DE60178ABA2CC7F4EB6401 /* PermissionsStepView.swift */; };
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@@ -742,6 +745,7 @@
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 		B460358B22184090D1CCD18E /* juno-68-stop.m4a */ = {isa = PBXFileReference; path = "juno-68-stop.m4a"; sourceTree = "<group>"; };
+		B48B1FA4FF13F4A4B56BD27D /* Monitoring.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = Monitoring.swift; sourceTree = "<group>"; };
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@@ -865,13 +869,23 @@
 			files = (
 				0A7FB8A90BB7E7A5110A4F4D /* BlurtEngine in Frameworks */,
 				A34A51EDE26BC24EB08A3900 /* AppUpdater in Frameworks */,
-				D6DFF322638007525EBA02B2 /* Sentry in Frameworks */,
+				D6DFF322638007525EBA02B2 /* DatadogCore in Frameworks */,
+				82FCEE1383634F9B88976992 /* DatadogLogs in Frameworks */,
+				6179B457E48877787CE028DA /* DatadogCrashReporting in Frameworks */,
 			);
 			runOnlyForDeploymentPostprocessing = 0;
 		};
 /* End PBXFrameworksBuildPhase section */
 
 /* Begin PBXGroup section */
+		0093069C3061D45801274652 /* Monitoring */ = {
+			isa = PBXGroup;
+			children = (
+				B48B1FA4FF13F4A4B56BD27D /* Monitoring.swift */,
+			);
+			path = Monitoring;
+			sourceTree = "<group>";
+		};
 		10E2E11380C974390308C1D2 /* Products */ = {
 			isa = PBXGroup;
 			children = (
@@ -896,6 +910,7 @@
 				7D6DE85EA50E7CD4CC977211 /* Branding */,
 				DF92BBDB4B9C15FAE100B783 /* Hotkey */,
 				8C67CBF637D85C0F642E53B5 /* MenuBar */,
+				0093069C3061D45801274652 /* Monitoring */,
 				912505E1D0FBD5D5CA591BA2 /* Overlay */,
 				DB755555AE4E89FE376399BF /* Resources */,
 				C9A477A17B95181CF6FCCB13 /* Shared */,
@@ -1448,7 +1463,9 @@
 			packageProductDependencies = (
 				371215E93A9C2CE60C6347BB /* BlurtEngine */,
 				B7FF7A7170C36BAABD1ECC90 /* AppUpdater */,
-				39EB6BB06E04EA9CD2CDC3BA /* Sentry */,
+				A0E6571699034CB1C08CB0C9 /* DatadogCore */,
+				056BF2B5954A44C3AEEC6DD2 /* DatadogLogs */,
+				45CD7152E18BFEE0F598216D /* DatadogCrashReporting */,
 			);
 			productName = Blurt;
 			productReference = 5E2309BDEF30ED9EFED5B849 /* Blurt.app */;
@@ -1485,7 +1502,7 @@
 			minimizedProjectReferenceProxies = 1;
 			packageReferences = (
 				1B0B6EAFD1174B4B9140D250 /* XCRemoteSwiftPackageReference "AppUpdater" */,
-				A70C65ACE504420011952EBA /* XCRemoteSwiftPackageReference "sentry-cocoa" */,
+				0F8ABF4083EB1DDD289350B7 /* XCRemoteSwiftPackageReference "dd-sdk-ios" */,
 				BFFF3588F0D8C2D0EEF7BC75 /* XCLocalSwiftPackageReference "../.." */,
 			);
 			preferredProjectObjectVersion = 77;
@@ -1955,6 +1972,7 @@
 				B5A7CEA6517E5A1E4D77623F /* FloatingPanel.swift in Sources */,
 				F42E6D4E62345772C5A49A08 /* HotkeyStepView.swift in Sources */,
 				AD32046355138298E7FC40D0 /* MenuBarScene.swift in Sources */,
+				9108B9B80FE4395A4D6D4F2C /* Monitoring.swift in Sources */,
 				9437C292A6D7FE533338073D /* OverlayView.swift in Sources */,
 				8FE4B9B139BB9557FBC5589B /* OverlayWindowController.swift in Sources */,
 				D750C1BF16502EEC92182ECD /* PermissionsStepView.swift in Sources */,
@@ -2231,33 +2249,43 @@
 /* End XCLocalSwiftPackageReference section */
 
 /* Begin XCRemoteSwiftPackageReference section */
-		1B0B6EAFD1174B4B9140D250 /* XCRemoteSwiftPackageReference "AppUpdater" */ = {
+		0F8ABF4083EB1DDD289350B7 /* XCRemoteSwiftPackageReference "dd-sdk-ios" */ = {
 			isa = XCRemoteSwiftPackageReference;
-			repositoryURL = "https://github.com/mxcl/AppUpdater";
+			repositoryURL = "https://github.com/DataDog/dd-sdk-ios";
 			requirement = {
 				kind = upToNextMajorVersion;
-				minimumVersion = 2.1.1;
+				minimumVersion = 3.13.0;
 			};
 		};
-		A70C65ACE504420011952EBA /* XCRemoteSwiftPackageReference "sentry-cocoa" */ = {
+		1B0B6EAFD1174B4B9140D250 /* XCRemoteSwiftPackageReference "AppUpdater" */ = {
 			isa = XCRemoteSwiftPackageReference;
-			repositoryURL = "https://github.com/getsentry/sentry-cocoa";
+			repositoryURL = "https://github.com/mxcl/AppUpdater";
 			requirement = {
 				kind = upToNextMajorVersion;
-				minimumVersion = 9.19.0;
+				minimumVersion = 2.1.1;
 			};
 		};
 /* End XCRemoteSwiftPackageReference section */
 
 /* Begin XCSwiftPackageProductDependency section */
+		056BF2B5954A44C3AEEC6DD2 /* DatadogLogs */ = {
+			isa = XCSwiftPackageProductDependency;
+			package = 0F8ABF4083EB1DDD289350B7 /* XCRemoteSwiftPackageReference "dd-sdk-ios" */;
+			productName = DatadogLogs;
+		};
 		371215E93A9C2CE60C6347BB /* BlurtEngine */ = {
 			isa = XCSwiftPackageProductDependency;
 			productName = BlurtEngine;
 		};
-		39EB6BB06E04EA9CD2CDC3BA /* Sentry */ = {
+		45CD7152E18BFEE0F598216D /* DatadogCrashReporting */ = {
+			isa = XCSwiftPackageProductDependency;
+			package = 0F8ABF4083EB1DDD289350B7 /* XCRemoteSwiftPackageReference "dd-sdk-ios" */;
+			productName = DatadogCrashReporting;
+		};
+		A0E6571699034CB1C08CB0C9 /* DatadogCore */ = {
 			isa = XCSwiftPackageProductDependency;
-			package = A70C65ACE504420011952EBA /* XCRemoteSwiftPackageReference "sentry-cocoa" */;
-			productName = Sentry;
+			package = 0F8ABF4083EB1DDD289350B7 /* XCRemoteSwiftPackageReference "dd-sdk-ios" */;
+			productName = DatadogCore;
 		};
 		B7FF7A7170C36BAABD1ECC90 /* AppUpdater */ = {
 			isa = XCSwiftPackageProductDependency;

App/Blurt/Blurt/AppCoordinator.swift

@@ -2,7 +2,6 @@ import AVFoundation
 import BlurtEngine
 import Foundation
 import Observation
-import Sentry
 
 @MainActor
 @Observable
@@ -328,18 +327,18 @@ final class AppCoordinator {
     }
     wasRecording = isRecording
 
-    // A .failed phase is a handled error (it doesn't crash the app), so Sentry's
-    // automatic crash reporting never sees it — report the genuine faults here.
+    // A .failed phase is a handled error (it doesn't crash the app), so the
+    // crash reporter never sees it — report the genuine faults here.
     if case .failed(let error) = phase {
-      reportFaultToSentry(error)
+      reportFault(error)
     }
   }
 
-  /// Reports a pipeline failure to Sentry, but only the genuine faults. The
+  /// Reports a pipeline failure to Datadog, but only the genuine faults. The
   /// permission- and key-missing cases are expected setup states the wizard
   /// already guides the user through, so reporting them would just be noise. The
   /// underlying error rides along as context for the wrapped cases.
-  private func reportFaultToSentry(_ error: BlurtError) {
+  private func reportFault(_ error: BlurtError) {
     switch error {
     case .microphonePermissionDenied, .accessibilityPermissionMissing, .apiKeyMissing:
       return
@@ -348,15 +347,13 @@ final class AppCoordinator {
       // but it's not a fault to report regardless — there was simply nowhere to type.
       return
     case .targetAppLost:
-      SentrySDK.capture(error: error)
+      Monitoring.reportError(error)
     case .sttFailed(let underlying), .audioCaptureFailed(let underlying):
       // A dropped/absent network connection isn't a Blurt fault — it's the
       // user being offline mid-dictation. The pipeline still surfaces a .failed
-      // phase to them; we just don't page Sentry about it.
+      // phase to them; we just don't report it.
       if Self.isConnectivityError(underlying) { return }
-      SentrySDK.capture(error: error) { scope in
-        scope.setExtra(value: String(describing: underlying), key: "underlying_error")
-      }
+      Monitoring.reportError(error, attributes: ["underlying_error": String(describing: underlying)])
     }
   }