diff --git a/src/selfhost/sentry.ts b/src/selfhost/sentry.ts
index 4edefda0ee..d19199bb53 100644
--- a/src/selfhost/sentry.ts
+++ b/src/selfhost/sentry.ts
@@ -87,6 +87,10 @@ export function captureReviewFailure(
   });
 }
 
+// The structured-log fields worth indexing as Sentry tags — the dimensions operators filter + group by. Only
+// string|number values are tagged; everything else stays in the full "log" context.
+const SENTRY_LOG_TAG_KEYS = ["repo", "repository", "installationId", "installation_id", "pull", "pullNumber", "pr", "project", "kind", "deliveryId"] as const;
+
 /** Forward a structured console line to Sentry when it is an ERROR-level log. The engine logs operational
  *  failures (orb_broker_unavailable, gate-check errors, relay drops, …) as JSON strings, often via console.error.
  *  No-op when Sentry is off, the line isn't a JSON object string, or its level isn't error/fatal — routine logs
@@ -104,16 +108,22 @@ export function forwardStructuredLogToSentry(line: unknown): void {
   const level = obj.level;
   if (level !== "error" && level !== "fatal") return;
   const severity = level === "fatal" ? "fatal" : "error";
-  const title =
-    typeof obj.event === "string"
-      ? obj.event
-      : typeof obj.message === "string"
-        ? obj.message
-        : "error";
+  const event = typeof obj.event === "string" ? obj.event : undefined;
+  // Lead the Sentry title with the real failure detail (message → error), not just the event slug, so an operator
+  // sees WHAT broke straight from the issue list instead of having to open the context blob.
+  const detail = typeof obj.message === "string" ? obj.message : typeof obj.error === "string" ? obj.error : undefined;
+  const title = event ? (detail ? `${event}: ${detail}` : event) : (detail ?? "error");
   Sentry.withScope((scope) => {
     scope.setLevel(severity);
     scope.setContext("log", obj);
-    if (typeof obj.event === "string") scope.setTag("event", obj.event);
+    if (event) scope.setTag("event", event);
+    // Index the dimensions operators filter + group by, so issues are findable without digging into the context.
+    for (const key of SENTRY_LOG_TAG_KEYS) {
+      const value = obj[key];
+      if (typeof value === "string" || typeof value === "number") scope.setTag(key, String(value));
+    }
+    // Group recurrences of ONE failure into a single issue (by event, not the variable detail that's in the title).
+    if (event) scope.setFingerprint(["gittensory-log", event]);
     Sentry!.captureMessage(title, severity);
   });
 }
diff --git a/test/unit/selfhost-sentry.test.ts b/test/unit/selfhost-sentry.test.ts
index 07316c1f27..fa283d1235 100644
--- a/test/unit/selfhost-sentry.test.ts
+++ b/test/unit/selfhost-sentry.test.ts
@@ -2,7 +2,7 @@ import { describe, it, expect, vi, beforeEach } from "vitest";
 
 // Mock @sentry/node so the dynamic import inside initSentry() resolves to spies. Hoisted so vi.mock can see it.
 const mocks = vi.hoisted(() => {
-  const scope = { setContext: vi.fn(), setLevel: vi.fn(), setTag: vi.fn() };
+  const scope = { setContext: vi.fn(), setLevel: vi.fn(), setTag: vi.fn(), setFingerprint: vi.fn() };
   return {
     scope,
     init: vi.fn(),
@@ -212,6 +212,26 @@ describe("forwardStructuredLogToSentry — central console.log → Sentry error
     );
   });
 
+  it("leads the title with the real error detail + indexes filterable tags + fingerprints by event (#observability)", async () => {
+    await initSentry({ SENTRY_DSN: "d" } as unknown as NodeJS.ProcessEnv);
+    forwardStructuredLogToSentry(
+      JSON.stringify({
+        level: "error",
+        event: "orb_broker_unavailable",
+        error: "The operation was aborted due to timeout",
+        repo: "JSONbored/gittensory",
+        installationId: 143010787,
+      }),
+    );
+    // The issue TITLE now carries the actual failure, not just the event slug — no hunting through the context blob.
+    expect(mocks.captureMessage).toHaveBeenCalledWith("orb_broker_unavailable: The operation was aborted due to timeout", "error");
+    // The present log dimensions become filterable tags.
+    expect(mocks.scope.setTag).toHaveBeenCalledWith("repo", "JSONbored/gittensory");
+    expect(mocks.scope.setTag).toHaveBeenCalledWith("installationId", "143010787");
+    // Recurrences of one failure group into a single issue by event.
+    expect(mocks.scope.setFingerprint).toHaveBeenCalledWith(["gittensory-log", "orb_broker_unavailable"]);
+  });
+
   it("forwards a level:fatal log titled by message (no event ⇒ no tag)", async () => {
     await initSentry({ SENTRY_DSN: "d" } as unknown as NodeJS.ProcessEnv);
     forwardStructuredLogToSentry(