diff --git a/.changeset/dev-ready-timeout.md b/.changeset/dev-ready-timeout.md
new file mode 100644
index 00000000..f02e99de
--- /dev/null
+++ b/.changeset/dev-ready-timeout.md
@@ -0,0 +1,5 @@
+---
+"@dawn-ai/cli": patch
+---
+
+`dawn dev` startup readiness timeout is now configurable via `DAWN_DEV_READY_TIMEOUT_MS` (default unchanged at 5s). Also de-flakes the dev-command disposal test that raced child startup against the readiness window in CI.
diff --git a/packages/cli/src/lib/dev/dev-session.ts b/packages/cli/src/lib/dev/dev-session.ts
index 24e490d3..7ecb4a88 100644
--- a/packages/cli/src/lib/dev/dev-session.ts
+++ b/packages/cli/src/lib/dev/dev-session.ts
@@ -263,7 +263,7 @@ class InternalDevSession {
 
     try {
       await child.waitForReady()
-      await waitForDevServerReady(this.url)
+      await waitForDevServerReady(this.url, { timeoutMs: readReadyTimeoutMs() })
     } catch (error) {
       await child.stop(readShutdownTimeoutMs())
 
@@ -399,3 +399,14 @@ function readShutdownTimeoutMs(): number {
   const parsedValue = Number(rawValue)
   return Number.isFinite(parsedValue) ? parsedValue : 1_000
 }
+
+function readReadyTimeoutMs(): number {
+  const rawValue = process.env.DAWN_DEV_READY_TIMEOUT_MS
+
+  if (!rawValue) {
+    return 5_000
+  }
+
+  const parsedValue = Number(rawValue)
+  return Number.isFinite(parsedValue) ? parsedValue : 5_000
+}
diff --git a/packages/cli/test/dev-command.test.ts b/packages/cli/test/dev-command.test.ts
index 4141fc61..15909d47 100644
--- a/packages/cli/test/dev-command.test.ts
+++ b/packages/cli/test/dev-command.test.ts
@@ -220,6 +220,7 @@ describe("dawn dev lifecycle", () => {
       env: {
         DAWN_DEV_CHILD_PID_PATH: pidPath,
         DAWN_DEV_CHILD_TEST_MODE: "report-ready-without-server",
+        DAWN_DEV_READY_TIMEOUT_MS: "15000",
       },
     })
     devProcesses.push(dev)
@@ -739,7 +740,7 @@ async function delay(ms: number): Promise<void> {
   await new Promise((resolve) => setTimeout(resolve, ms))
 }
 
-async function waitForPath(path: string, timeoutMs = 2_000): Promise<void> {
+async function waitForPath(path: string, timeoutMs = 10_000): Promise<void> {
   const startedAt = Date.now()
 
   while (Date.now() - startedAt < timeoutMs) {