diff --git a/src/cli/run/runner.ts b/src/cli/run/runner.ts
index a648417af..30e46688f 100644
--- a/src/cli/run/runner.ts
+++ b/src/cli/run/runner.ts
@@ -6,6 +6,8 @@ import { createEventState, processEvents, serializeError } from "./events"
 
 const POLL_INTERVAL_MS = 500
 const DEFAULT_TIMEOUT_MS = 0
+const SESSION_CREATE_MAX_RETRIES = 3
+const SESSION_CREATE_RETRY_DELAY_MS = 1000
 
 export async function run(options: RunOptions): Promise<number> {
   const {
@@ -45,13 +47,49 @@ export async function run(options: RunOptions): Promise<number> {
     })
 
     try {
-      const sessionRes = await client.session.create({
-        body: { title: "oh-my-opencode run" },
-      })
+      // Retry session creation with exponential backoff
+      // Server might not be fully ready even after "listening" message
+      let sessionID: string | undefined
+      let lastError: unknown
+
+      for (let attempt = 1; attempt <= SESSION_CREATE_MAX_RETRIES; attempt++) {
+        const sessionRes = await client.session.create({
+          body: { title: "oh-my-opencode run" },
+        })
+
+        if (sessionRes.error) {
+          lastError = sessionRes.error
+          console.error(pc.yellow(`Session create attempt ${attempt}/${SESSION_CREATE_MAX_RETRIES} failed:`))
+          console.error(pc.dim(`  Error: ${serializeError(sessionRes.error)}`))
+
+          if (attempt < SESSION_CREATE_MAX_RETRIES) {
+            const delay = SESSION_CREATE_RETRY_DELAY_MS * attempt
+            console.log(pc.dim(`  Retrying in ${delay}ms...`))
+            await new Promise((resolve) => setTimeout(resolve, delay))
+            continue
+          }
+        }
+
+        sessionID = sessionRes.data?.id
+        if (sessionID) {
+          break
+        }
+
+        // No error but also no session ID - unexpected response
+        lastError = new Error(`Unexpected response: ${JSON.stringify(sessionRes, null, 2)}`)
+        console.error(pc.yellow(`Session create attempt ${attempt}/${SESSION_CREATE_MAX_RETRIES}: No session ID returned`))
+
+        if (attempt < SESSION_CREATE_MAX_RETRIES) {
+          const delay = SESSION_CREATE_RETRY_DELAY_MS * attempt
+          console.log(pc.dim(`  Retrying in ${delay}ms...`))
+          await new Promise((resolve) => setTimeout(resolve, delay))
+        }
+      }
 
-      const sessionID = sessionRes.data?.id
       if (!sessionID) {
-        console.error(pc.red("Failed to create session"))
+        console.error(pc.red("Failed to create session after all retries"))
+        console.error(pc.dim(`Last error: ${serializeError(lastError)}`))
+        cleanup()
         return 1
       }