diff --git a/.changeset/stale-cache-recovery.md b/.changeset/stale-cache-recovery.md
new file mode 100644
index 00000000..b8c9367d
--- /dev/null
+++ b/.changeset/stale-cache-recovery.md
@@ -0,0 +1,5 @@
+---
+"twilio-run": patch
+---
+
+Automatically recover from stale `.twiliodeployinfo` cache entries during deploy. When a cached service SID references a service that was deleted externally (via Console or API), the deploy now detects the 20404 error, clears the stale cache entry, and retries the deployment instead of failing with a confusing error message.
diff --git a/packages/twilio-run/src/commands/deploy.ts b/packages/twilio-run/src/commands/deploy.ts
index 62034037..0c6c135d 100644
--- a/packages/twilio-run/src/commands/deploy.ts
+++ b/packages/twilio-run/src/commands/deploy.ts
@@ -20,6 +20,7 @@ import {
 } from '../flags';
 import { printConfigInfo, printDeployedResources } from '../printers/deploy';
 import { HttpError, saveLatestDeploymentData } from '../serverless-api/utils';
+import { clearDeployInfoCache } from '../utils/deployInfoCache';
 import {
   getDebugFunction,
   getOraSpinner,
@@ -123,7 +124,31 @@ export async function handler(
     client.on('status-update', (evt) => {
       spinner.text = evt.message + '\n';
     });
-    const result = await client.deployLocalProject(config);
+
+    let result;
+    try {
+      result = await client.deployLocalProject(config);
+    } catch (deployErr) {
+      // If the cached service SID is stale (service was deleted externally),
+      // clear the cache and retry without the stale SID
+      const isStaleService = config.serviceSid && deployErr.code === 20404;
+      if (isStaleService) {
+        const accountSid = config.username.startsWith('AC')
+          ? config.username
+          : externalCliOptions?.accountSid;
+        logger.warn(
+          `Cached service ${config.serviceSid} not found (it may have been deleted). Clearing cache and retrying.`
+        );
+        if (accountSid) {
+          clearDeployInfoCache(config.cwd, accountSid, config.region);
+        }
+        config.serviceSid = undefined;
+        result = await client.deployLocalProject(config);
+      } else {
+        throw deployErr;
+      }
+    }
+
     spinner.text = 'Serverless project successfully deployed\n';
     spinner.succeed();
     printDeployedResources(config, result, config.outputFormat);
diff --git a/packages/twilio-run/src/utils/deployInfoCache.ts b/packages/twilio-run/src/utils/deployInfoCache.ts
index 9218b18d..d9618211 100644
--- a/packages/twilio-run/src/utils/deployInfoCache.ts
+++ b/packages/twilio-run/src/utils/deployInfoCache.ts
@@ -58,6 +58,30 @@ export function getDeployInfoCache(
   return {};
 }
 
+export function clearDeployInfoCache(
+  baseDir: string,
+  username: string,
+  region: string = 'us1',
+  deployInfoCacheFileName: string = '.twiliodeployinfo'
+): void {
+  const fullPath = path.resolve(baseDir, deployInfoCacheFileName);
+  debug('Clearing stale deploy info cache entry for %s:%s', username, region);
+  const currentDeployInfoCache = getDeployInfoCache(
+    baseDir,
+    deployInfoCacheFileName
+  );
+
+  delete currentDeployInfoCache[`${username}:${region}`];
+  delete currentDeployInfoCache[username];
+
+  try {
+    const data = JSON.stringify(currentDeployInfoCache, null, '\t');
+    fs.writeFileSync(fullPath, data, 'utf8');
+  } catch (err) {
+    debug('Failed to clear deploy info cache entry');
+  }
+}
+
 export function updateDeployInfoCache(
   baseDir: string,
   username: string,