diff --git a/src/selfhost/queue-common.ts b/src/selfhost/queue-common.ts
index 63fdd9a33a..3739a57263 100644
--- a/src/selfhost/queue-common.ts
+++ b/src/selfhost/queue-common.ts
@@ -1,3 +1,5 @@
+import { createHash } from "node:crypto";
+
 import { retryableJobDelayMs } from "../queue/retryable";
 import {
   LOW_REST_RATE_LIMIT_REMAINING,
@@ -650,7 +652,8 @@ function normalizedPathScope(value: unknown): string | null {
         .map((entry) => entry.trim()),
     ),
   ].sort();
-  return paths.length > 0 ? JSON.stringify(paths) : null;
+  if (paths.length === 0) return null;
+  return `sha256:${createHash("sha256").update(JSON.stringify(paths)).digest("hex")}`;
 }
 
 function boolFlag(value: unknown): string {
diff --git a/test/unit/selfhost-queue-common.test.ts b/test/unit/selfhost-queue-common.test.ts
index 8623b652cf..d5b267d21d 100644
--- a/test/unit/selfhost-queue-common.test.ts
+++ b/test/unit/selfhost-queue-common.test.ts
@@ -560,7 +560,7 @@ describe("self-host queue common helpers", () => {
           paths: ["README.md", "src/a.ts", "README.md"],
         }),
       ),
-    ).toBe('rag-index-repo:jsonbored/gittensory:["README.md","src/a.ts"]');
+    ).toBe("rag-index-repo:jsonbored/gittensory:sha256:8812e979fc698c98d98665ad4ccd8630e396dabdce08ebf87b41600c94bb1df5");
     expect(
       jobCoalesceKey(
         payload({
@@ -570,7 +570,7 @@ describe("self-host queue common helpers", () => {
           paths: ["a,b", "c"],
         }),
       ),
-    ).toBe('rag-index-repo:jsonbored/gittensory:["a,b","c"]');
+    ).toBe("rag-index-repo:jsonbored/gittensory:sha256:569c363fb7e855f85eeae4e4dc032d1f8d262191b68ade7297566486982b5183");
     expect(
       jobCoalesceKey(
         payload({
@@ -580,7 +580,27 @@ describe("self-host queue common helpers", () => {
           paths: ["a", "b,c"],
         }),
       ),
-    ).toBe('rag-index-repo:jsonbored/gittensory:["a","b,c"]');
+    ).toBe("rag-index-repo:jsonbored/gittensory:sha256:472ecd0a16762a33c3090345032fcadcfe6b34ee43a5cce5385fef8e72169c92");
+    const longPathKey = jobCoalesceKey(
+      payload({
+        type: "rag-index-repo",
+        requestedBy: "webhook",
+        repoFullName: "JSONbored/Gittensory",
+        paths: Array.from({ length: 100 }, (_, index) => `src/${index}-${"a".repeat(220)}.ts`),
+      }),
+    );
+    expect(longPathKey).toMatch(/^rag-index-repo:jsonbored\/gittensory:sha256:[a-f0-9]{64}$/);
+    expect(longPathKey?.length).toBe("rag-index-repo:jsonbored/gittensory:sha256:".length + 64);
+    expect(
+      jobCoalesceKey(
+        payload({
+          type: "rag-index-repo",
+          requestedBy: "webhook",
+          repoFullName: "JSONbored/Gittensory",
+          paths: [" ", null],
+        }),
+      ),
+    ).toBe("rag-index-repo:jsonbored/gittensory:full");
     expect(jobCoalesceKey(payload({ type: "prune-retention", requestedBy: "schedule", dryRun: true }))).toBe(
       "prune-retention:1",
     );
diff --git a/test/unit/selfhost-sqlite-queue.test.ts b/test/unit/selfhost-sqlite-queue.test.ts
index f111b93194..2e06d528b3 100644
--- a/test/unit/selfhost-sqlite-queue.test.ts
+++ b/test/unit/selfhost-sqlite-queue.test.ts
@@ -892,8 +892,8 @@ describe("createSqliteQueue (durable #980)", () => {
       "backfill-registered-repos:jsonbored/gittensory:light:1",
       "generate-weekly-value-report:operator:7",
       "generate-weekly-value-report:public:7",
-      'rag-index-repo:jsonbored/gittensory:["src/a.ts","src/b.ts"]',
-      'rag-index-repo:jsonbored/gittensory:["src/c.ts"]',
+      "rag-index-repo:jsonbored/gittensory:sha256:170cb2cfb288ab59ba4d35b2633120223c9acc6893fd5baec3465c434ad5bedf",
+      "rag-index-repo:jsonbored/gittensory:sha256:f4f9970f7a842b1b7b619cbd49f05da577a7d725ff1616ba2de8beed1ae5616f",
     ]);
     expect(rows.map((row) => JSON.parse(row.payload).requestedBy)).toEqual([
       "api",