diff --git a/src/servers/sidecar/create-proxy.ts b/src/servers/sidecar/create-proxy.ts
index b0fa94f5..a3984412 100644
--- a/src/servers/sidecar/create-proxy.ts
+++ b/src/servers/sidecar/create-proxy.ts
@@ -157,7 +157,21 @@ export function createSidecarProxy({
     const server = ctx.env as { timeout?: (req: Request, seconds: number) => void } | undefined;
     // `0` disables the idle timeout. With the switch on, an undeclared plugin falls back to the server's
     // own 60s default by not being touched at all.
-    const inbound = TIMEOUTS_ON ? timeoutSeconds : (timeoutSeconds ?? 0);
+    /*
+      Bun stores a per-request timeout in ONE BYTE. Anything above 255 seconds is clamped to 255 — so a
+      plugin declaring a generous 1800 got a SHORTER timeout than a plugin declaring nothing at all, which
+      falls through to 0 and is unlimited. Declaring the fix is what armed the bomb.
+
+      That is what killed every long transcription: 1800 became 255, the upload took a second, and the
+      connection dropped at 4m16s while whisperx went on and finished the job into a dead socket. Six
+      plugins declare more than 255 — transcribe and email at 1800, music at 1800, jellyfin at 3600,
+      minesweeper and photos at 600 — and all six were getting 255.
+
+      So anything Bun cannot represent becomes 0: a plugin asking for longer than Bun's maximum is asking
+      for "do not cut this off", and 0 is the only value that means it.
+    */
+    const requested = TIMEOUTS_ON ? timeoutSeconds : (timeoutSeconds ?? 0);
+    const inbound = requested !== undefined && requested > 255 ? 0 : requested;
     if (inbound !== undefined) {
       try {
         server?.timeout?.(ctx.req.raw, inbound);