diff --git a/cli/src/shared/agent-setup.ts b/cli/src/shared/agent-setup.ts
index b1366cb6..8df68fc4 100644
--- a/cli/src/shared/agent-setup.ts
+++ b/cli/src/shared/agent-setup.ts
@@ -4,7 +4,7 @@
 import { writeFileSync, unlinkSync } from "node:fs";
 import { tmpdir } from "node:os";
 import { join } from "node:path";
-import { logInfo, logWarn, logError, logStep, prompt, jsonEscape } from "./ui";
+import { logInfo, logWarn, logError, logStep, prompt, jsonEscape, withRetry } from "./ui";
 import type { AgentConfig } from "./agents";
 
 // Re-export so cloud modules can re-export from here
@@ -28,7 +28,12 @@ export async function installAgent(
 ): Promise<void> {
   logStep(`Installing ${agentName}...`);
   try {
-    await runner.runServer(installCmd, timeoutSecs);
+    await withRetry(
+      `${agentName} install`,
+      () => runner.runServer(installCmd, timeoutSecs),
+      2,
+      10,
+    );
   } catch {
     logError(`${agentName} installation failed`);
     throw new Error(`${agentName} install failed`);
@@ -45,11 +50,18 @@ export async function uploadConfigFile(runner: CloudRunner, content: string, rem
     mode: 0o600,
   });
 
-  const tempRemote = `/tmp/spawn_config_${Date.now()}`;
   try {
-    await runner.uploadFile(tmpFile, tempRemote);
-    await runner.runServer(
-      `mkdir -p $(dirname "${remotePath}") && chmod 600 '${tempRemote}' && mv '${tempRemote}' "${remotePath}"`,
+    await withRetry(
+      "config upload",
+      async () => {
+        const tempRemote = `/tmp/spawn_config_${Date.now()}`;
+        await runner.uploadFile(tmpFile, tempRemote);
+        await runner.runServer(
+          `mkdir -p $(dirname "${remotePath}") && chmod 600 '${tempRemote}' && mv '${tempRemote}' "${remotePath}"`,
+        );
+      },
+      2,
+      5,
     );
   } finally {
     try {
diff --git a/cli/src/shared/orchestrate.ts b/cli/src/shared/orchestrate.ts
index dc66b8f2..7ef1ade3 100644
--- a/cli/src/shared/orchestrate.ts
+++ b/cli/src/shared/orchestrate.ts
@@ -3,7 +3,7 @@
 
 import type { AgentConfig } from "./agents";
 import { generateEnvConfig } from "./agents";
-import { logInfo, logStep, logWarn } from "./ui";
+import { logInfo, logStep, logWarn, withRetry } from "./ui";
 import { getOrPromptApiKey, getModelIdInteractive } from "./oauth";
 import type { CloudRunner } from "./agent-setup";
 import { offerGithubAuth } from "./agent-setup";
@@ -64,10 +64,16 @@ export async function runOrchestration(cloud: CloudOrchestrator, agent: AgentCon
   const envContent = generateEnvConfig(agent.envVars(apiKey));
   const envB64 = Buffer.from(envContent).toString("base64");
   try {
-    await cloud.runner.runServer(
-      `printf '%s' '${envB64}' | base64 -d > ~/.spawnrc && chmod 600 ~/.spawnrc; ` +
-        `grep -q 'source ~/.spawnrc' ~/.bashrc 2>/dev/null || echo '[ -f ~/.spawnrc ] && source ~/.spawnrc' >> ~/.bashrc; ` +
-        `grep -q 'source ~/.spawnrc' ~/.zshrc 2>/dev/null || echo '[ -f ~/.spawnrc ] && source ~/.spawnrc' >> ~/.zshrc`,
+    await withRetry(
+      "env setup",
+      () =>
+        cloud.runner.runServer(
+          `printf '%s' '${envB64}' | base64 -d > ~/.spawnrc && chmod 600 ~/.spawnrc; ` +
+            `grep -q 'source ~/.spawnrc' ~/.bashrc 2>/dev/null || echo '[ -f ~/.spawnrc ] && source ~/.spawnrc' >> ~/.bashrc; ` +
+            `grep -q 'source ~/.spawnrc' ~/.zshrc 2>/dev/null || echo '[ -f ~/.spawnrc ] && source ~/.spawnrc' >> ~/.zshrc`,
+        ),
+      2,
+      5,
     );
   } catch {
     logWarn("Environment setup had errors");
@@ -79,7 +85,7 @@ export async function runOrchestration(cloud: CloudOrchestrator, agent: AgentCon
   // 10. Agent-specific configuration
   if (agent.configure) {
     try {
-      await agent.configure(apiKey, modelId);
+      await withRetry("agent config", () => agent.configure!(apiKey, modelId), 2, 5);
     } catch {
       logWarn("Agent configuration failed (continuing with defaults)");
     }
diff --git a/cli/src/shared/ui.ts b/cli/src/shared/ui.ts
index e8fbafba..6c8507dc 100644
--- a/cli/src/shared/ui.ts
+++ b/cli/src/shared/ui.ts
@@ -149,6 +149,25 @@ export function openBrowser(url: string): void {
   logStep(`Please open: ${url}`);
 }
 
+/** Generic async retry helper. Retries `fn` up to `maxAttempts` times with a delay between attempts. */
+export async function withRetry<T>(
+  label: string,
+  fn: () => Promise<T>,
+  maxAttempts = 3,
+  delaySec = 5,
+): Promise<T> {
+  for (let attempt = 1; attempt <= maxAttempts; attempt++) {
+    try {
+      return await fn();
+    } catch (err) {
+      if (attempt >= maxAttempts) throw err;
+      logWarn(`${label} failed (attempt ${attempt}/${maxAttempts}), retrying in ${delaySec}s...`);
+      await new Promise((r) => setTimeout(r, delaySec * 1000));
+    }
+  }
+  throw new Error("unreachable");
+}
+
 /** JSON-escape a string (returns the quoted JSON string). */
 export function jsonEscape(s: string): string {
   return JSON.stringify(s);