diff --git a/extensions/bluebubbles/src/send.test.ts b/extensions/bluebubbles/src/send.test.ts
index 412fdff03cd..527774412b1 100644
--- a/extensions/bluebubbles/src/send.test.ts
+++ b/extensions/bluebubbles/src/send.test.ts
@@ -1041,23 +1041,62 @@ describe("send", () => {
         }
       });
 
-      it("does not refresh when no reply or effect is requested", async () => {
-        // Cache expired but no Private API features needed — skip refresh
+      // Plain-text sends also need the cache populated so `isMacOS26OrHigher`
+      // can read `os_version` from the same `serverInfoCache`. Without a
+      // refresh on cold/expired cache, macOS 26 detection would silently
+      // miss and force-route would fall back to broken AppleScript.
+      // (Greptile/Codex PR #69070)
+      it("refreshes cache for plain-text sends when status is unknown", async () => {
+        // First call returns null (cache cold/expired). The refresh path
+        // fetches server info; plain-text send still uses AppleScript when
+        // Private API is disabled on the server — but the refresh ran.
+        privateApiStatusMock.mockReturnValueOnce(null).mockReturnValueOnce(false);
+        fetchServerInfoMock.mockResolvedValueOnce({ private_api: false });
         mockResolvedHandleTarget();
-        mockSendResponse({ data: { guid: "msg-plain" } });
+        mockSendResponse({ data: { guid: "msg-plain-refreshed" } });
 
         const result = await sendMessageBlueBubbles("+15551234567", "Plain message", {
           serverUrl: "http://localhost:1234",
           password: "test",
         });
 
-        expect(result.messageId).toBe("msg-plain");
-        expect(fetchServerInfoMock).not.toHaveBeenCalled();
+        expect(result.messageId).toBe("msg-plain-refreshed");
+        expect(fetchServerInfoMock).toHaveBeenCalledTimes(1);
         const sendCall = mockFetch.mock.calls[1];
         const body = JSON.parse(sendCall[1].body);
         expect(body.method).toBe("apple-script");
       });
 
+      // Cold cache + macOS 26 + Private API enabled on refresh — the
+      // refresh populates the cache, `isMacOS26OrHigher` returns true, and
+      // plain-text routes through Private API instead of broken AppleScript.
+      // (Greptile/Codex PR #69070)
+      it("force-routes macOS 26 plain-text through Private API after cold-cache refresh", async () => {
+        privateApiStatusMock.mockReturnValueOnce(null).mockReturnValueOnce(true);
+        fetchServerInfoMock.mockResolvedValueOnce({
+          private_api: true,
+          os_version: "26.0",
+        });
+        isMacOS26OrHigherMock.mockReturnValue(true);
+        mockResolvedHandleTarget();
+        mockSendResponse({ data: { guid: "msg-macos26-refreshed" } });
+
+        try {
+          const result = await sendMessageBlueBubbles("+15551234567", "Plain message", {
+            serverUrl: "http://localhost:1234",
+            password: "test",
+          });
+
+          expect(result.messageId).toBe("msg-macos26-refreshed");
+          expect(fetchServerInfoMock).toHaveBeenCalledTimes(1);
+          const sendCall = mockFetch.mock.calls[1];
+          const body = JSON.parse(sendCall[1].body);
+          expect(body.method).toBe("private-api");
+        } finally {
+          isMacOS26OrHigherMock.mockReturnValue(false);
+        }
+      });
+
       it("degrades gracefully when refresh returns null (server unreachable)", async () => {
         // Cache expired, refresh returns null (server info unavailable)
         fetchServerInfoMock.mockResolvedValueOnce(null);
diff --git a/extensions/bluebubbles/src/send.ts b/extensions/bluebubbles/src/send.ts
index 4d6c725506e..a2506a73ca5 100644
--- a/extensions/bluebubbles/src/send.ts
+++ b/extensions/bluebubbles/src/send.ts
@@ -482,10 +482,14 @@ export async function sendMessageBlueBubbles(
   const wantsReplyThread = normalizeOptionalString(opts.replyToMessageGuid) !== undefined;
   const wantsEffect = Boolean(effectId);
 
-  // Lazy refresh: when the cache has expired and Private API features are needed,
-  // fetch server info before making the decision. This prevents silent degradation
-  // of reply threading and effects after the 10-minute cache TTL expires. (#43764)
-  if (privateApiStatus === null && (wantsReplyThread || wantsEffect)) {
+  // Lazy refresh: when the cache has expired, fetch server info before
+  // making the decision. Originally scoped to reply/effect features (#43764)
+  // to avoid silent degradation after the 10-minute cache TTL expires. Now
+  // always fires on null status, because `isMacOS26OrHigher()` reads from
+  // the same cache and plain-text sends on macOS 26 need Private API too —
+  // without this, `forceOnMacOS26` silently falls back to broken AppleScript
+  // after TTL expiry or on a cold cache. (#64480, Greptile/Codex PR #69070)
+  if (privateApiStatus === null) {
     try {
       await fetchBlueBubblesServerInfo({
         baseUrl,