Improve Reddit chat and media reliability

apps/dashboard/src/features/conversations/conversation-detail.tsx

@@ -27,7 +27,7 @@ function MessageHistory({ conversation }: { conversation: ConversationDetailResp
   return (
     <ol aria-label="Message history" className="conversation-messages">
       {conversation.messages.map((message) => (
-        <li className={message.isSelf ? 'is-self' : 'is-recipient'} key={`${message.timestamp}-${message.sender}-${message.text}`}>
+        <li className={message.isSelf ? 'is-self' : 'is-recipient'} key={message.eventId ?? `${message.timestamp}-${message.sender}-${message.text}`}>
           <div>
             <strong>{message.isSelf
               ? `You${conversation.owner ? ` (u/${conversation.owner.redditUsername})` : ''}`

extensions/reddit-session-exporter/README.md

@@ -14,4 +14,4 @@ This local Chrome extension exports `reddit.com` cookies and the current Reddit
 
 The extension observes only requests to Reddit's Matrix homeservers, verifies the captured token with Matrix `whoami`, reads Reddit cookies, and saves the combined export locally. It does not send the dump to any server; you upload it directly to your RedditBot dashboard.
 
-Before downloading, the extension independently resolves the current Reddit cookie identity and refuses the export unless its `t2` account ID matches Matrix `whoami`. Changing Reddit accounts clears the stored Matrix capture, so Reddit Chat must be reopened after every account switch.
+Before downloading, the extension independently resolves the current identity through the open `www.reddit.com` tab and refuses the export unless its `t2` account ID matches Matrix `whoami`. If you switch accounts, reload Reddit Chat so the extension captures that account's current Matrix token.

extensions/reddit-session-exporter/manifest.json

@@ -3,7 +3,7 @@
   "name": "RedditBot Session Exporter",
   "version": "1.1.1",
   "description": "Exports Reddit cookies and Reddit Chat credentials for a self-hosted RedditBot dashboard.",
-  "permissions": ["cookies", "downloads", "storage", "webRequest"],
+  "permissions": ["cookies", "downloads", "scripting", "storage", "webRequest"],
   "host_permissions": [
     "https://reddit.com/*",
     "https://*.reddit.com/*",

extensions/reddit-session-exporter/service-worker.js

@@ -26,27 +26,40 @@ chrome.webRequest.onBeforeSendHeaders.addListener(
     });
     await chrome.action.setBadgeText({ text: 'OK' });
     await chrome.action.setBadgeBackgroundColor({ color: '#198754' });
+    await chrome.action.setTitle({ title: 'Reddit Chat token captured. Click to export.' });
   },
   { urls: MATRIX_URLS },
   ['requestHeaders', 'extraHeaders'],
 );
 
-chrome.cookies.onChanged.addListener(async ({ cookie }) => {
-  if (!['reddit_session', 'token_v2'].includes(cookie.name)) return;
-  await chrome.storage.local.remove('matrixCapture');
-  await chrome.action.setBadgeText({ text: '' });
-  await chrome.action.setTitle({
-    title: 'Reddit account changed. Open Reddit Chat before exporting.',
-  });
-});
-
 async function getRedditIdentity() {
-  const response = await fetch('https://www.reddit.com/api/me.json', {
+  const tabs = await chrome.tabs.query({
-    credentials: 'include',
+    url: ['https://reddit.com/*', 'https://www.reddit.com/*'],
-    cache: 'no-store',
   });
-  if (!response.ok) throw new Error('Reddit cookies did not authenticate. Sign in and try again.');
+  const tab = tabs.find((candidate) => candidate.active) ?? tabs[0];
-  const payload = await response.json();
+  if (tab?.id === undefined) {
+    throw new Error('Keep a signed-in www.reddit.com tab open while exporting.');
+  }
+
+  const [{ result } = {}] = await chrome.scripting.executeScript({
+    target: { tabId: tab.id },
+    world: 'MAIN',
+    func: async () => {
+      try {
+        const response = await fetch('https://www.reddit.com/api/me.json', {
+          credentials: 'include',
+          cache: 'no-store',
+        });
+        if (!response.ok) return { error: 'Reddit cookies did not authenticate. Sign in and try again.' };
+        return { payload: await response.json() };
+      } catch {
+        return { error: 'Could not read the current Reddit account. Reload Reddit and try again.' };
+      }
+    },
+  });
+
+  if (result?.error) throw new Error(result.error);
+  const payload = result?.payload;
   const account = payload?.data ?? payload;
   if (!account?.name || !account?.id) {
     throw new Error('Reddit did not return an authenticated account identity.');
@@ -93,6 +106,8 @@ chrome.action.onClicked.addListener(async () => {
       ...createSessionExportDownload(cookies, { ...matrixCapture, userId: identity.user_id }),
       saveAs: true,
     });
+    await chrome.action.setBadgeText({ text: 'OK' });
+    await chrome.action.setTitle({ title: 'RedditBot session export created.' });
   } catch (error) {
     await showError(error instanceof Error ? error.message : 'Could not create the session dump.');
   }

package-lock.json

@@ -11,7 +11,7 @@
       "dependencies": {
         "@tanstack/react-query": "^5.90.20",
         "axios": "^1.13.2",
-        "better-sqlite3": "^12.5.0",
+        "better-sqlite3": "^13.0.3",
         "dotenv": "^17.2.3",
         "express": "^5.2.1",
         "openai": "^6.15.0",
@@ -2258,26 +2258,6 @@
         "node": ">= 6"
       }
     },
-    "node_modules/base64-js": {
-      "version": "1.5.1",
-      "resolved": "https://registry.npmjs.org/base64-js/-/base64-js-1.5.1.tgz",
-      "integrity": "sha512-AKpaYlHn8t4SVbOHCy+b5+KKgvR4vrsD8vbvrbiQJps7fKDTkjkDry6ji0rUJjC0kzbNePLwzxq8iypo41qeWA==",
-      "funding": [
-        {
-          "type": "github",
-          "url": "https://github.com/sponsors/feross"
-        },
-        {
-          "type": "patreon",
-          "url": "https://www.patreon.com/feross"
-        },
-        {
-          "type": "consulting",
-          "url": "https://feross.org/support"
-        }
-      ],
-      "license": "MIT"
-    },
     "node_modules/baseline-browser-mapping": {
       "version": "2.11.12",
       "resolved": "https://registry.npmjs.org/baseline-browser-mapping/-/baseline-browser-mapping-2.11.12.tgz",
@@ -2292,17 +2272,15 @@
       }
     },
     "node_modules/better-sqlite3": {
-      "version": "12.5.0",
+      "version": "13.0.3",
-      "resolved": "https://registry.npmjs.org/better-sqlite3/-/better-sqlite3-12.5.0.tgz",
+      "resolved": "https://registry.npmjs.org/better-sqlite3/-/better-sqlite3-13.0.3.tgz",
-      "integrity": "sha512-WwCZ/5Diz7rsF29o27o0Gcc1Du+l7Zsv7SYtVPG0X3G/uUI1LqdxrQI7c9Hs2FWpqXXERjW9hp6g3/tH7DlVKg==",
+      "integrity": "sha512-RbOBxmLBG8uvFUc15X9+9SFemKcQ0WBuISBVkpuiaUB2qblC8UWlHEjdWVoZ8AdhSwmoEgsiXKfopX0CQxaACQ==",
-      "hasInstallScript": true,
       "license": "MIT",
       "dependencies": {
-        "bindings": "^1.5.0",
+        "node-addon-api": "^8.0.0"
-        "prebuild-install": "^7.1.1"
       },
       "engines": {
-        "node": "20.x || 22.x || 23.x || 24.x || 25.x"
+        "node": ">=22"
       }
     },
     "node_modules/bidi-js": {
@@ -2315,26 +2293,6 @@
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       }
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-      "license": "MIT",
-      "dependencies": {
-        "file-uri-to-path": "1.0.0"
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-      "integrity": "sha512-1W07cM9gS6DcLperZfFSj+bWLtaPGSOHWhPiGzXmvVJbRLdG82sH/Kn8EtW1VqWVA54AKf2h5k5BbnIbwF3h6w==",
-      "license": "MIT",
-      "dependencies": {
-        "buffer": "^5.5.0",
-        "inherits": "^2.0.4",
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     "node_modules/body-parser": {
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       "resolved": "https://registry.npmjs.org/body-parser/-/body-parser-2.3.0.tgz",
@@ -2406,30 +2364,6 @@
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-      "funding": [
-        {
-          "type": "github",
-          "url": "https://github.com/sponsors/feross"
-        },
-        {
-          "type": "patreon",
-          "url": "https://www.patreon.com/feross"
-        },
-        {
-          "type": "consulting",
-          "url": "https://feross.org/support"
-        }
-      ],
-      "license": "MIT",
-      "dependencies": {
-        "base64-js": "^1.3.1",
-        "ieee754": "^1.1.13"
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@@ -2499,12 +2433,6 @@
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@@ -2717,30 +2645,6 @@
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-      "license": "MIT",
-      "dependencies": {
-        "mimic-response": "^3.1.0"
-      },
-      "engines": {
-        "node": ">=10"
-      },
-      "funding": {
-        "url": "https://github.com/sponsors/sindresorhus"
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-    "node_modules/deep-extend": {
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-      "resolved": "https://registry.npmjs.org/deep-extend/-/deep-extend-0.6.0.tgz",
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-      "engines": {
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@@ -2769,15 +2673,6 @@
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-      "license": "Apache-2.0",
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@@ -2847,15 +2742,6 @@
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@@ -3004,15 +2890,6 @@
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@@ -3229,12 +3100,6 @@
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@@ -3328,12 +3193,6 @@
         "url": "https://github.com/privatenumber/get-tsconfig?sponsor=1"
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@@ -3483,26 +3342,6 @@
         "url": "https://opencollective.com/express"
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-        },
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-          "type": "consulting",
-          "url": "https://feross.org/support"
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@@ -4048,18 +3607,6 @@
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       }
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-    "node_modules/mimic-response": {
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-      "resolved": "https://registry.npmjs.org/mimic-response/-/mimic-response-3.1.0.tgz",
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@@ -4070,21 +3617,6 @@
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-      "license": "MIT",
-      "funding": {
-        "url": "https://github.com/sponsors/ljharb"
-      }
-    },
-    "node_modules/mkdirp-classic": {
-      "version": "0.5.3",
-      "resolved": "https://registry.npmjs.org/mkdirp-classic/-/mkdirp-classic-0.5.3.tgz",
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-      "license": "MIT"
-    },
     "node_modules/ms": {
       "version": "2.1.3",
       "resolved": "https://registry.npmjs.org/ms/-/ms-2.1.3.tgz",
@@ -4186,12 +3718,6 @@
         "node": "^10 || ^12 || ^13.7 || ^14 || >=15.0.1"
       }
     },
-    "node_modules/napi-build-utils": {
-      "version": "2.0.0",
-      "resolved": "https://registry.npmjs.org/napi-build-utils/-/napi-build-utils-2.0.0.tgz",
-      "integrity": "sha512-GEbrYkbfF7MoNaoh2iGG84Mnf/WZfB0GdGEsM8wz7Expx/LlWf5U8t9nvJKXSp3qr5IsEbK04cBGhol/KwOsWA==",
-      "license": "MIT"
-    },
     "node_modules/negotiator": {
       "version": "1.0.0",
       "resolved": "https://registry.npmjs.org/negotiator/-/negotiator-1.0.0.tgz",
@@ -4201,16 +3727,13 @@
         "node": ">= 0.6"
       }
     },
-    "node_modules/node-abi": {
+    "node_modules/node-addon-api": {
-      "version": "3.85.0",
+      "version": "8.9.1",
-      "resolved": "https://registry.npmjs.org/node-abi/-/node-abi-3.85.0.tgz",
+      "resolved": "https://registry.npmjs.org/node-addon-api/-/node-addon-api-8.9.1.tgz",
-      "integrity": "sha512-zsFhmbkAzwhTft6nd3VxcG0cvJsT70rL+BIGHWVq5fi6MwGrHwzqKaxXE+Hl2GmnGItnDKPPkO5/LQqjVkIdFg==",
+      "integrity": "sha512-4eUQWVPCUUUiBjLnHS3cXWeC6ryoPUc0U3rP7IuzapoGbzMqd/r6KKO0clr0b+snQhsrueFEhCZDdK+LK7hxKg==",
       "license": "MIT",
-      "dependencies": {
-        "semver": "^7.3.5"
-      },
       "engines": {
-        "node": ">=10"
+        "node": "^18 || ^20 || >= 21"
       }
     },
     "node_modules/node-releases": {
@@ -4465,32 +3988,6 @@
         "node": "^10 || ^12 || >=14"
       }
     },
-    "node_modules/prebuild-install": {
-      "version": "7.1.3",
-      "resolved": "https://registry.npmjs.org/prebuild-install/-/prebuild-install-7.1.3.tgz",
-      "integrity": "sha512-8Mf2cbV7x1cXPUILADGI3wuhfqWvtiLA1iclTDbFRZkgRQS0NqsPZphna9V+HyTEadheuPmjaJMsbzKQFOzLug==",
-      "license": "MIT",
-      "dependencies": {
-        "detect-libc": "^2.0.0",
-        "expand-template": "^2.0.3",
-        "github-from-package": "0.0.0",
-        "minimist": "^1.2.3",
-        "mkdirp-classic": "^0.5.3",
-        "napi-build-utils": "^2.0.0",
-        "node-abi": "^3.3.0",
-        "pump": "^3.0.0",
-        "rc": "^1.2.7",
-        "simple-get": "^4.0.0",
-        "tar-fs": "^2.0.0",
-        "tunnel-agent": "^0.6.0"
-      },
-      "bin": {
-        "prebuild-install": "bin.js"
-      },
-      "engines": {
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-      }
-    },
     "node_modules/pretty-format": {
       "version": "27.5.1",
       "resolved": "https://registry.npmjs.org/pretty-format/-/pretty-format-27.5.1.tgz",
@@ -4529,16 +4026,6 @@
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       }
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-      "version": "3.0.3",
-      "resolved": "https://registry.npmjs.org/pump/-/pump-3.0.3.tgz",
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-      "license": "MIT",
-      "dependencies": {
-        "end-of-stream": "^1.1.0",
-        "once": "^1.3.1"
-      }
-    },
     "node_modules/punycode": {
       "version": "2.3.1",
       "resolved": "https://registry.npmjs.org/punycode/-/punycode-2.3.1.tgz",
@@ -4589,21 +4076,6 @@
         "node": ">= 0.10"
       }
     },
-    "node_modules/rc": {
-      "version": "1.2.8",
-      "resolved": "https://registry.npmjs.org/rc/-/rc-1.2.8.tgz",
-      "integrity": "sha512-y3bGgqKj3QBdxLbLkomlohkvsA8gdAiUQlSBJnBhfn+BPxg4bc62d8TcBW15wavDfgexCgccckhcZvywyQYPOw==",
-      "license": "(BSD-2-Clause OR MIT OR Apache-2.0)",
-      "dependencies": {
-        "deep-extend": "^0.6.0",
-        "ini": "~1.3.0",
-        "minimist": "^1.2.0",
-        "strip-json-comments": "~2.0.1"
-      },
-      "bin": {
-        "rc": "cli.js"
-      }
-    },
     "node_modules/react": {
       "version": "19.2.8",
       "resolved": "https://registry.npmjs.org/react/-/react-19.2.8.tgz",
@@ -4881,18 +4353,6 @@
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       "license": "MIT"
     },
-    "node_modules/semver": {
-      "version": "7.7.3",
-      "resolved": "https://registry.npmjs.org/semver/-/semver-7.7.3.tgz",
-      "integrity": "sha512-SdsKMrI9TdgjdweUSR9MweHA4EJ8YxHn8DFaDisvhVlUOe4BF1tLD7GAj0lIqWVl+dPb/rExr0Btby5loQm20Q==",
-      "license": "ISC",
-      "bin": {
-        "semver": "bin/semver.js"
-      },
-      "engines": {
-        "node": ">=10"
-      }
-    },
     "node_modules/send": {
       "version": "1.2.1",
       "resolved": "https://registry.npmjs.org/send/-/send-1.2.1.tgz",
@@ -5068,51 +4528,6 @@
         "url": "https://github.com/sponsors/isaacs"
       }
     },
-    "node_modules/simple-concat": {
-      "version": "1.0.1",
-      "resolved": "https://registry.npmjs.org/simple-concat/-/simple-concat-1.0.1.tgz",
-      "integrity": "sha512-cSFtAPtRhljv69IK0hTVZQ+OfE9nePi/rtJmw5UjHeVyVroEqJXP1sFztKUy1qU+xvz3u/sfYJLa947b7nAN2Q==",
-      "funding": [
-        {
-          "type": "github",
-          "url": "https://github.com/sponsors/feross"
-        },
-        {
-          "type": "patreon",
-          "url": "https://www.patreon.com/feross"
-        },
-        {
-          "type": "consulting",
-          "url": "https://feross.org/support"
-        }
-      ],
-      "license": "MIT"
-    },
-    "node_modules/simple-get": {
-      "version": "4.0.1",
-      "resolved": "https://registry.npmjs.org/simple-get/-/simple-get-4.0.1.tgz",
-      "integrity": "sha512-brv7p5WgH0jmQJr1ZDDfKDOSeWWg+OVypG99A/5vYGPqJ6pxiaHLy8nxtFjBA7oMa01ebA9gfh1uMCFqOuXxvA==",
-      "funding": [
-        {
-          "type": "github",
-          "url": "https://github.com/sponsors/feross"
-        },
-        {
-          "type": "patreon",
-          "url": "https://www.patreon.com/feross"
-        },
-        {
-          "type": "consulting",
-          "url": "https://feross.org/support"
-        }
-      ],
-      "license": "MIT",
-      "dependencies": {
-        "decompress-response": "^6.0.0",
-        "once": "^1.3.1",
-        "simple-concat": "^1.0.0"
-      }
-    },
     "node_modules/source-map-js": {
       "version": "1.2.1",
       "resolved": "https://registry.npmjs.org/source-map-js/-/source-map-js-1.2.1.tgz",
@@ -5212,15 +4627,6 @@
         "node": ">=8"
       }
     },
-    "node_modules/strip-json-comments": {
-      "version": "2.0.1",
-      "resolved": "https://registry.npmjs.org/strip-json-comments/-/strip-json-comments-2.0.1.tgz",
-      "integrity": "sha512-4gB8na07fecVVkOI6Rs4e7T6NOTki5EmL7TUduTs6bu3EdnSycntVJ4re8kgZA+wx9IueI2Y11bfbgwtzuE0KQ==",
-      "license": "MIT",
-      "engines": {
-        "node": ">=0.10.0"
-      }
-    },
     "node_modules/symbol-tree": {
       "version": "3.2.4",
       "resolved": "https://registry.npmjs.org/symbol-tree/-/symbol-tree-3.2.4.tgz",
@@ -5241,34 +4647,6 @@
         "url": "https://github.com/sponsors/sindresorhus"
       }
     },
-    "node_modules/tar-fs": {
-      "version": "2.1.4",
-      "resolved": "https://registry.npmjs.org/tar-fs/-/tar-fs-2.1.4.tgz",
-      "integrity": "sha512-mDAjwmZdh7LTT6pNleZ05Yt65HC3E+NiQzl672vQG38jIrehtJk/J3mNwIg+vShQPcLF/LV7CMnDW6vjj6sfYQ==",
-      "license": "MIT",
-      "dependencies": {
-        "chownr": "^1.1.1",
-        "mkdirp-classic": "^0.5.2",
-        "pump": "^3.0.0",
-        "tar-stream": "^2.1.4"
-      }
-    },
-    "node_modules/tar-stream": {
-      "version": "2.2.0",
-      "resolved": "https://registry.npmjs.org/tar-stream/-/tar-stream-2.2.0.tgz",
-      "integrity": "sha512-ujeqbceABgwMZxEJnk2HDY2DlnUZ+9oEcb1KzTVfYHio0UE6dG71n60d8D2I4qNvleWrrXpmjpt7vZeF1LnMZQ==",
-      "license": "MIT",
-      "dependencies": {
-        "bl": "^4.0.3",
-        "end-of-stream": "^1.4.1",
-        "fs-constants": "^1.0.0",
-        "inherits": "^2.0.3",
-        "readable-stream": "^3.1.1"
-      },
-      "engines": {
-        "node": ">=6"
-      }
-    },
     "node_modules/text-hex": {
       "version": "1.0.0",
       "resolved": "https://registry.npmjs.org/text-hex/-/text-hex-1.0.0.tgz",
@@ -5418,18 +4796,6 @@
         "node": "^8.16.0 || ^10.6.0 || >=11.0.0"
       }
     },
-    "node_modules/tunnel-agent": {
-      "version": "0.6.0",
-      "resolved": "https://registry.npmjs.org/tunnel-agent/-/tunnel-agent-0.6.0.tgz",
-      "integrity": "sha512-McnNiV1l8RYeY8tBgEpuodCC1mLUdbSN+CYBL7kJsJNInOP8UjDDEwdk6Mw60vdLLrr5NHKZhMAOSrR2NZuQ+w==",
-      "license": "Apache-2.0",
-      "dependencies": {
-        "safe-buffer": "^5.0.1"
-      },
-      "engines": {
-        "node": "*"
-      }
-    },
     "node_modules/type-fest": {
       "version": "5.8.0",
       "resolved": "https://registry.npmjs.org/type-fest/-/type-fest-5.8.0.tgz",

package.json

@@ -26,7 +26,7 @@
   "dependencies": {
     "@tanstack/react-query": "^5.90.20",
     "axios": "^1.13.2",
-    "better-sqlite3": "^12.5.0",
+    "better-sqlite3": "^13.0.3",
     "dotenv": "^17.2.3",
     "express": "^5.2.1",
     "openai": "^6.15.0",

packages/api-contracts/src/chats.ts

@@ -8,6 +8,7 @@ export const ChatMediaSchema = z.strictObject({
   fileName: z.string(),
 });
 export const ChatMessageSchema = z.strictObject({
+  eventId: z.string().optional(),
   sender: z.string(),
   text: z.string(),
   timestamp: z.number(),

src/services/chat/service.ts

@@ -17,6 +17,7 @@ import type { AccountAuthGate } from '../account-auth-context.js';
 
 const ACTIVE_WINDOW_MS = 96 * 60 * 60 * 1000;
 const ROOM_URL_PREFIX = 'https://chat.reddit.com/room/';
+const OPTIMISTIC_RECONCILIATION_WINDOW_MS = 2_000;
 
 export interface TokenRefresher {
   /**
@@ -221,6 +222,19 @@ export class ChatService {
 
   async loadCache(): Promise<void> {
     await this.cache.load();
+    let repairedDuplicateMessages = 0;
+    for (const chat of this.cache.get()) {
+      if (!chat.messages || chat.messages.length < 2) continue;
+      const normalized = this.normalizeMessages(chat.messages, true);
+      repairedDuplicateMessages += chat.messages.length - normalized.length;
+      chat.messages = normalized;
+    }
+    if (repairedDuplicateMessages > 0) {
+      this.logger.info(
+        `[chat] removed ${repairedDuplicateMessages} legacy optimistic message duplicate(s) from cache`,
+      );
+      await this.cache.save();
+    }
     for (const chat of this.cache.get()) {
       const t2 = this.extractT2(chat);
       if (t2 && chat.username && !chat.username.startsWith('t2_')) {
@@ -632,7 +646,7 @@ export class ChatService {
           url: ROOM_URL_PREFIX + encodeURIComponent(roomId),
           roomId,
           messages: [
-            { sender: 'Me', text: message, timestamp: Date.now(), isSelf: true },
+            { eventId, sender: 'Me', text: message, timestamp: Date.now(), isSelf: true },
           ],
           originMessage: message,
         };
@@ -822,6 +836,7 @@ export class ChatService {
         const body = (e.content.body as string | undefined) ?? '';
         const mxc = typeof e.content.url === 'string' ? (e.content.url as string) : null;
         return {
+          eventId: e.event_id,
           sender: e.sender === this.matrix.userId ? 'Me' : this.shortenSender(e.sender),
           text: body || (mxc ? '[Image]' : ''),
           timestamp: e.origin_server_ts,
@@ -833,13 +848,87 @@ export class ChatService {
 
   private mergeNewMessages(chat: ActiveChat, newMessages: ChatMessage[]): void {
     if (!chat.messages || chat.messages.length === 0) return;
-    const seen = new Set(chat.messages.map((m) => `${m.timestamp}|${m.sender}`));
+    chat.messages = this.normalizeMessages([...chat.messages, ...newMessages]);
-    for (const msg of newMessages) {
+  }
-      const key = `${msg.timestamp}|${msg.sender}`;
+
-      if (seen.has(key)) continue;
+  /**
-      chat.messages.push(msg);
+   * Matrix event IDs are authoritative. The content/time fallback only
-      seen.add(key);
+   * exists to repair cache entries written before ChatMessage stored them.
+   */
+  private normalizeMessages(
+    messages: ChatMessage[],
+    repairLegacyOpeningDuplicate = false,
+  ): ChatMessage[] {
+    const normalized: ChatMessage[] = [];
+    const eventIndexes = new Map<string, number>();
+    const fallbackKeys = new Set<string>();
+
+    for (const message of messages) {
+      if (message.eventId) {
+        const existingIndex = eventIndexes.get(message.eventId);
+        if (existingIndex !== undefined) {
+          const existing = normalized[existingIndex];
+          normalized[existingIndex] = {
+            ...existing,
+            ...message,
+            media: message.media ?? existing.media,
+          };
+          continue;
+        }
+
+        const optimisticIndex = normalized.findIndex((candidate) =>
+          !candidate.eventId
+          && candidate.isSelf
+          && message.isSelf
+          && candidate.sender === message.sender
+          && candidate.text === message.text
+          && Math.abs(candidate.timestamp - message.timestamp)
+            <= OPTIMISTIC_RECONCILIATION_WINDOW_MS,
+        );
+        if (optimisticIndex !== -1) {
+          normalized[optimisticIndex] = {
+            ...normalized[optimisticIndex],
+            ...message,
+            media: message.media ?? normalized[optimisticIndex].media,
+          };
+          eventIndexes.set(message.eventId, optimisticIndex);
+          continue;
+        }
+
+        eventIndexes.set(message.eventId, normalized.length);
+        normalized.push(message);
+        continue;
+      }
+
+      const fallbackKey = `${message.timestamp}|${message.sender}|${message.text}`;
+      if (fallbackKeys.has(fallbackKey)) continue;
+      fallbackKeys.add(fallbackKey);
+      normalized.push(message);
     }
+
+    normalized.sort((a, b) => a.timestamp - b.timestamp);
+
+    // Before event IDs were persisted, startConversation cached a Date.now()
+    // copy and /sync appended the same opening send with the server timestamp.
+    // Restrict legacy repair to the opening pair and self-authored text so two
+    // genuine repeated messages elsewhere in a conversation remain intact.
+    if (repairLegacyOpeningDuplicate && normalized.length >= 2) {
+      const first = normalized[0];
+      const second = normalized[1];
+      if (
+        !first.eventId
+        && !second.eventId
+        && first.isSelf
+        && second.isSelf
+        && first.sender === second.sender
+        && first.text === second.text
+        && second.timestamp - first.timestamp <= OPTIMISTIC_RECONCILIATION_WINDOW_MS
+      ) {
+        normalized.splice(1, 1);
+      }
+    }
+
+    return normalized;
   }
 
   private async loadDetails(chat: ActiveChat): Promise<void> {
@@ -866,6 +955,7 @@ export class ChatService {
       const body = (e.content.body as string | undefined) ?? '';
       const mxc = typeof e.content.url === 'string' ? (e.content.url as string) : null;
       return {
+        eventId: e.event_id,
         sender: e.sender === this.matrix.userId ? 'Me' : this.shortenSender(e.sender),
         text: body || (mxc ? '[Image]' : ''),
         timestamp: e.origin_server_ts,
@@ -890,9 +980,10 @@ export class ChatService {
       }
     }
 
-    chat.messages = this.mediaService
+    const attachedMessages = this.mediaService
       ? await this.mediaService.attachMedia(chat, scraped)
       : scraped.map(({ mediaUrls: _ignored, ...m }) => m as ChatMessage);
+    chat.messages = this.normalizeMessages(attachedMessages);
 
     if (chat.messages.length === 0) {
       this.logger.debug(`[chat] no messages in ${chat.roomName}`);

src/services/chat/types.ts

@@ -1,4 +1,6 @@
 export interface ChatMessage {
+  /** Stable Matrix identity used to reconcile optimistic sends with /sync. */
+  eventId?: string;
   sender: string;
   text: string;
   timestamp: number;

src/services/media.ts

@@ -76,6 +76,7 @@ export class MediaService {
     for (const message of messages) {
       const media = await this.downloadMessageMedia(chat, message);
       updated.push({
+        eventId: message.eventId,
         sender: message.sender,
         text: message.text,
         timestamp: message.timestamp,

src/web/routes/media.ts

@@ -31,7 +31,8 @@ export function createMediaRouter(ctx: WebContext): Router {
       const byRoom = new Map(liveChats.map((c) => [`${c.accountId}:${c.roomId ?? ''}`, c] as const));
 
       res.json(items.map((item) => {
-        const live = item.chatRoomId ? byRoom.get(`${item.accountId ?? ''}:${item.chatRoomId}`) : undefined;
+        const { accountId, ...publicItem } = item;
+        const live = item.chatRoomId ? byRoom.get(`${accountId ?? ''}:${item.chatRoomId}`) : undefined;
         const username = resolveRedditUsername(
           live?.username ?? item.chatUsername,
           ctx.services.chat,
@@ -39,11 +40,11 @@ export function createMediaRouter(ctx: WebContext): Router {
         const sender = /^(me|you)$/i.test(item.sender)
           ? 'You'
           : resolveRedditUsername(item.sender, ctx.services.chat) ?? username ?? 'Unknown Reddit user';
-        const account = item.accountId
+        const account = accountId
-          ? ctx.services.redditAccounts?.get(item.accountId)
+          ? ctx.services.redditAccounts?.get(accountId)
           : null;
         return {
-          ...item,
+          ...publicItem,
           chatUsername: username,
           sender,
           urlPath: `/media/${item.relativePath.split(/[\\/]/).map(encodeURIComponent).join('/')}`,

tests/chat-service-text-sync.test.ts

@@ -85,7 +85,7 @@ describe('ChatService text delta sync', () => {
     const [conversation] = await service.getCachedConversations();
     expect(conversation.messages).toEqual([
       { sender: 'alice', text: 'hello', timestamp: now - 1_000, isSelf: false },
-      { sender: 'Me', text: 'AI-assisted reply', timestamp: now, isSelf: true },
+      { eventId: '$sent', sender: 'Me', text: 'AI-assisted reply', timestamp: now, isSelf: true },
     ]);
 
     const persisted = JSON.parse(await fs.readFile(cacheFile, 'utf-8')) as {
@@ -93,4 +93,139 @@ describe('ChatService text delta sync', () => {
     };
     expect(persisted.chats[0].messages).toHaveLength(2);
   });
+
+  it('reconciles an optimistic opening message with its Matrix event', async () => {
+    const directory = await fs.mkdtemp(path.join(os.tmpdir(), 'chat-text-reconcile-'));
+    temporaryDirectories.push(directory);
+    const cacheFile = path.join(directory, 'chat-cache.json');
+    const serverTimestamp = Date.now();
+    await fs.writeFile(cacheFile, JSON.stringify({
+      version: 1,
+      savedAt: serverTimestamp,
+      chats: [{
+        username: 'alice',
+        roomName: 'alice',
+        roomId: '!alice:example.test',
+        lastMessageTime: serverTimestamp + 80,
+        lastMessageSnippet: 'hello',
+        isFromUs: true,
+        unread: false,
+        messages: [{
+          eventId: '$opening',
+          sender: 'Me',
+          text: 'hello',
+          timestamp: serverTimestamp + 80,
+          isSelf: true,
+        }],
+      }],
+      nextBatch: 's1',
+      lastDeltaSyncAt: serverTimestamp,
+    }), 'utf-8');
+
+    const logger = createMockLogger();
+    const matrix = new MatrixClient({
+      homeserver: 'https://matrix.example.test',
+      accessToken: 'token',
+      userId: '@me:example.test',
+      capturedAt: serverTimestamp,
+    }, logger, { minRequestIntervalMs: 0 });
+    matrix.sync = vi.fn(async () => ({
+      next_batch: 's2',
+      rooms: {
+        join: {
+          '!alice:example.test': {
+            timeline: {
+              events: [{
+                event_id: '$opening',
+                type: 'm.room.message',
+                sender: '@me:example.test',
+                origin_server_ts: serverTimestamp,
+                content: { msgtype: 'm.text', body: 'hello' },
+              }],
+            },
+          },
+        },
+      },
+    })) as typeof matrix.sync;
+
+    const service = new ChatService(
+      matrix,
+      logger,
+      undefined,
+      undefined,
+      undefined,
+      undefined,
+      new ChatCache(logger, cacheFile),
+      undefined,
+      undefined,
+      authenticatedAccountAuth,
+    );
+    await service.loadCache();
+    await service.refreshTopChats();
+
+    const [conversation] = await service.getCachedConversations();
+    expect(conversation.messages).toEqual([{
+      eventId: '$opening',
+      sender: 'Me',
+      text: 'hello',
+      timestamp: serverTimestamp,
+      isSelf: true,
+    }]);
+  });
+
+  it('repairs a legacy cached opening-message duplicate', async () => {
+    const directory = await fs.mkdtemp(path.join(os.tmpdir(), 'chat-text-legacy-repair-'));
+    temporaryDirectories.push(directory);
+    const cacheFile = path.join(directory, 'chat-cache.json');
+    const serverTimestamp = Date.now();
+    const message = { sender: 'Me', text: 'hello', isSelf: true };
+    await fs.writeFile(cacheFile, JSON.stringify({
+      version: 1,
+      savedAt: serverTimestamp,
+      chats: [{
+        username: 'alice',
+        roomName: 'alice',
+        roomId: '!alice:example.test',
+        lastMessageTime: serverTimestamp,
+        lastMessageSnippet: 'hello',
+        isFromUs: true,
+        unread: false,
+        messages: [
+          { ...message, timestamp: serverTimestamp + 80 },
+          { ...message, timestamp: serverTimestamp },
+        ],
+      }],
+      nextBatch: 's1',
+      lastDeltaSyncAt: serverTimestamp,
+    }), 'utf-8');
+
+    const logger = createMockLogger();
+    const matrix = new MatrixClient({
+      homeserver: 'https://matrix.example.test',
+      accessToken: 'token',
+      userId: '@me:example.test',
+      capturedAt: serverTimestamp,
+    }, logger, { minRequestIntervalMs: 0 });
+    const service = new ChatService(
+      matrix,
+      logger,
+      undefined,
+      undefined,
+      undefined,
+      undefined,
+      new ChatCache(logger, cacheFile),
+      undefined,
+      undefined,
+      authenticatedAccountAuth,
+    );
+
+    await service.loadCache();
+
+    const [conversation] = await service.getCachedConversations();
+    expect(conversation.messages).toEqual([{ ...message, timestamp: serverTimestamp }]);
+    const persisted = JSON.parse(await fs.readFile(cacheFile, 'utf-8')) as {
+      chats: Array<{ messages: unknown[] }>;
+    };
+    expect(persisted.chats[0].messages).toHaveLength(1);
+  });
 });

tests/chat-service-username-persist.test.ts

@@ -94,6 +94,9 @@ describe('ChatService username persistence', () => {
     const chat = await svc.startConversation('alice', 'hello', 't2_abc123');
 
     expect(chat?.username).toBe('alice');
+    expect(chat?.messages).toEqual([
+      expect.objectContaining({ eventId: '$event', text: 'hello', isSelf: true }),
+    ]);
     expect(usernameResolver.resolveUsernameToT2).not.toHaveBeenCalled();
     expect(matrix.sendInitialDirectMessage).toHaveBeenCalledWith(
       '@t2_abc123:reddit.com',

tests/web/media-route.test.ts

@@ -1,6 +1,7 @@
 import express from 'express';
 import type { AddressInfo } from 'node:net';
 import { afterEach, describe, expect, it, vi } from 'vitest';
+import { MediaResponseSchema } from '../../packages/api-contracts/src/media.js';
 import type { WebContext } from '../../src/web/context.js';
 import { createMediaRouter } from '../../src/web/routes/media.js';
 
@@ -63,4 +64,35 @@ describe('media route username presentation', () => {
     expect(JSON.stringify(body)).not.toContain('t2_missing');
     expect(body[0]).toMatchObject({ chatUsername: null, sender: 'Unknown Reddit user' });
   });
+
+  it('keeps the internal account ID out of the public media item', async () => {
+    const context = {
+      logger: { error: vi.fn() },
+      services: {
+        media: { getMediaItems: vi.fn().mockResolvedValue([{
+          accountId: 't2_owner', id: 'one', chatUsername: 'alice', chatRoomId: 'room-one', sender: 'alice',
+          timestamp: 1, originalUrl: 'mxc://one', fileName: 'one.jpg', relativePath: 'one.jpg', createdAt: 2,
+        }]) },
+        chat: {
+          getCachedConversations: vi.fn().mockResolvedValue([]),
+          resolveSenderDisplay: vi.fn((identity: string) => identity),
+        },
+        redditAccounts: {
+          get: vi.fn().mockReturnValue({ accountId: 't2_owner', redditUsername: 'owner' }),
+        },
+      },
+    } as unknown as WebContext;
+    const app = express().use('/api', createMediaRouter(context));
+
+    const response = await request(app, '/api/media');
+    const body: unknown = await response.json();
+
+    expect(MediaResponseSchema.parse(body)).toEqual([
+      expect.objectContaining({
+        id: 'one',
+        owner: { accountId: 't2_owner', redditUsername: 'owner' },
+      }),
+    ]);
+    expect(body).not.toEqual([expect.objectContaining({ accountId: expect.anything() })]);
+  });
 });