diff --git a/packages/cli/src/shared/agent-setup.ts b/packages/cli/src/shared/agent-setup.ts
index 0b3677a6..d84d7912 100644
--- a/packages/cli/src/shared/agent-setup.ts
+++ b/packages/cli/src/shared/agent-setup.ts
@@ -51,7 +51,7 @@ async function installAgent(
 ): Promise<void> {
   logStep(`Installing ${agentName}...`);
   const r = await asyncTryCatch(() =>
-    withRetry(`${agentName} install`, () => wrapSshCall(runner.runServer(installCmd, timeoutSecs)), 2, 10),
+    withRetry(`${agentName} install`, () => wrapSshCall(runner.runServer(installCmd, timeoutSecs)), 4, 10, true),
   );
   if (!r.ok) {
     logError(`${agentName} installation failed`);
@@ -82,8 +82,9 @@ async function uploadConfigFile(runner: CloudRunner, content: string, remotePath
             );
           })(),
         ),
-      2,
+      4,
       5,
+      true,
     ),
   );
   tryCatchIf(isOperationalError, () => unlinkSync(tmpFile));
diff --git a/packages/cli/src/shared/ui.ts b/packages/cli/src/shared/ui.ts
index 2de35f68..cbcfa47f 100644
--- a/packages/cli/src/shared/ui.ts
+++ b/packages/cli/src/shared/ui.ts
@@ -213,6 +213,7 @@ export async function withRetry<T>(
   fn: () => Promise<Result<T>>,
   maxAttempts = 3,
   delaySec = 5,
+  exponential = false,
 ): Promise<T> {
   for (let attempt = 1; attempt <= maxAttempts; attempt++) {
     const result = await fn(); // throws → not retried (non-retryable)
@@ -222,8 +223,9 @@ export async function withRetry<T>(
     if (attempt >= maxAttempts) {
       throw result.error;
     }
-    logWarn(`${label} failed (attempt ${attempt}/${maxAttempts}), retrying in ${delaySec}s...`);
-    await new Promise((r) => setTimeout(r, delaySec * 1000));
+    const delay = exponential ? delaySec * 2 ** (attempt - 1) : delaySec;
+    logWarn(`${label} failed (attempt ${attempt}/${maxAttempts}), retrying in ${delay}s...`);
+    await new Promise((r) => setTimeout(r, delay * 1000));
   }
   throw new Error("unreachable");
 }