diff --git a/src/server/lib/github/__tests__/cacheRequest.test.ts b/src/server/lib/github/__tests__/cacheRequest.test.ts
index 247834c8..63636007 100644
--- a/src/server/lib/github/__tests__/cacheRequest.test.ts
+++ b/src/server/lib/github/__tests__/cacheRequest.test.ts
@@ -44,6 +44,7 @@ describe('cacheRequest', () => {
   let logger: {
     debug: jest.Mock;
     info: jest.Mock;
+    warn: jest.Mock;
     error: jest.Mock;
   };
 
@@ -54,6 +55,7 @@ describe('cacheRequest', () => {
     logger = {
       debug: jest.fn(),
       info: jest.fn(),
+      warn: jest.fn(),
       error: jest.fn(),
     };
     (redisClient.getRedis as jest.Mock).mockReturnValue(cache);
@@ -328,4 +330,78 @@ describe('cacheRequest', () => {
     expect(cache.hset).toHaveBeenCalledTimes(1);
     expect(cache.expire).not.toHaveBeenCalled();
   });
+
+  describe('transient failures', () => {
+    beforeEach(() => {
+      jest.useFakeTimers();
+    });
+
+    afterEach(() => {
+      jest.useRealTimers();
+    });
+
+    it('retries a GET that fails with a server error and returns the eventual response', async () => {
+      const endpoint = 'GET /repos/acme/widget/git/trees/abc123';
+      const response = { status: 200, headers: {}, data: { tree: [] } };
+      request
+        .mockRejectedValueOnce(Object.assign(new Error('other side closed'), { status: 500 }))
+        .mockResolvedValueOnce(response);
+
+      const pending = cacheRequest(endpoint, {}, { cache });
+      await jest.advanceTimersByTimeAsync(10_000);
+      const result = await pending;
+
+      expect(result).toBe(response);
+      expect(request).toHaveBeenCalledTimes(2);
+      expect(logger.warn).toHaveBeenCalledWith('GitHub: cache request retrying');
+      expect(getLogger).toHaveBeenCalledWith({ endpoint, status: 500 });
+      expect(cache.hset).toHaveBeenCalledTimes(1);
+    });
+
+    it('does not retry a non-GET endpoint, so a write is never duplicated', async () => {
+      const endpoint = 'POST /repos/acme/widget/deployments';
+      request.mockRejectedValue(Object.assign(new Error('other side closed'), { status: 500 }));
+
+      const assertion = expect(cacheRequest(endpoint, { data: { ref: 'main' } }, { cache })).rejects.toMatchObject({
+        message: 'GitHub API request failed',
+      });
+      await jest.advanceTimersByTimeAsync(10_000);
+      await assertion;
+
+      expect(request).toHaveBeenCalledTimes(1);
+      expect(logger.warn).not.toHaveBeenCalled();
+    });
+
+    it('still retries when a 304 refetch is what hits the server error', async () => {
+      const endpoint = 'GET /repos/acme/widget';
+      const response = { status: 200, headers: {}, data: { id: 17 } };
+      cache.hgetall.mockResolvedValue({ etag: '"stale-etag"', lastModified: '', data: 'not-json' });
+      request
+        .mockRejectedValueOnce(Object.assign(new Error('Not Modified'), { status: 304 }))
+        .mockRejectedValueOnce(Object.assign(new Error('other side closed'), { status: 500 }))
+        .mockResolvedValueOnce(response);
+
+      const pending = cacheRequest(endpoint, {}, { cache });
+      await jest.advanceTimersByTimeAsync(10_000);
+
+      expect(await pending).toBe(response);
+      expect(request).toHaveBeenCalledTimes(3);
+      expect(logger.warn).toHaveBeenCalledTimes(1);
+    });
+
+    it('retries only once, then gives up', async () => {
+      const endpoint = 'GET /repos/acme/widget';
+      request.mockRejectedValue(Object.assign(new Error('other side closed'), { status: 500 }));
+
+      const assertion = expect(cacheRequest(endpoint, {}, { cache })).rejects.toMatchObject({
+        message: 'GitHub API request failed',
+      });
+      await jest.advanceTimersByTimeAsync(10_000);
+      await assertion;
+
+      expect(request).toHaveBeenCalledTimes(2);
+      expect(logger.warn).toHaveBeenCalledTimes(1);
+      expect(logger.error).toHaveBeenCalledWith('GitHub: cache request failed');
+    });
+  });
 });
diff --git a/src/server/lib/github/cacheRequest.ts b/src/server/lib/github/cacheRequest.ts
index 733678fe..f96940f6 100644
--- a/src/server/lib/github/cacheRequest.ts
+++ b/src/server/lib/github/cacheRequest.ts
@@ -22,10 +22,12 @@ import { CacheRequestData } from 'server/lib/github/types';
 
 import { redisClient } from 'server/lib/dependencies';
 
+const TRANSIENT_RETRY_DELAY_MS = 10_000;
+
 export async function cacheRequest(
   endpoint: string,
   requestData = {} as CacheRequestData,
-  { cache = redisClient.getRedis(), ignoreCache = false } = {}
+  { cache = redisClient.getRedis(), ignoreCache = false, retried = false } = {}
 ) {
   const cacheKey = `github:req_cache:${endpoint}`;
   let cached;
@@ -73,11 +75,18 @@ export async function cacheRequest(
         getLogger({ endpoint, cacheHit: true }).debug('GitHub: cache request hit');
         return { data, cacheHit: true };
       } catch (error) {
-        return cacheRequest(endpoint, requestData, { cache, ignoreCache: true });
+        return cacheRequest(endpoint, requestData, { cache, ignoreCache: true, retried });
       }
     } else if (error?.status === 404) {
       getLogger().info(`GitHub: cache request not found endpoint=${endpoint}`);
       throw new Error('Resource not found');
+    } else if (!retried && endpoint.startsWith('GET ') && error?.status >= 500) {
+      // Octokit reports a dropped keep-alive socket as status 500, indistinguishable from a real 5xx.
+      // The wait is long enough to miss the same dead socket, and short enough that a sleeping
+      // retry does not outlive a worker's shutdown grace and leave its job to stall recovery.
+      getLogger({ endpoint, status: error.status }).warn('GitHub: cache request retrying');
+      await new Promise((resolve) => setTimeout(resolve, TRANSIENT_RETRY_DELAY_MS));
+      return cacheRequest(endpoint, requestData, { cache, ignoreCache, retried: true });
     } else {
       const errorHeaders = error?.response?.headers || error?.headers;
       getLogger({