diff --git a/.changeset/loud-actors-remember.md b/.changeset/loud-actors-remember.md
new file mode 100644
index 000000000..f53652196
--- /dev/null
+++ b/.changeset/loud-actors-remember.md
@@ -0,0 +1,5 @@
+---
+"trigger.dev": patch
+---
+
+Default to retrying enabled in dev when running init
diff --git a/packages/cli-v3/src/templates/trigger.config.ts.template b/packages/cli-v3/src/templates/trigger.config.ts.template
index cf1ea31e7..b524e950e 100644
--- a/packages/cli-v3/src/templates/trigger.config.ts.template
+++ b/packages/cli-v3/src/templates/trigger.config.ts.template
@@ -4,7 +4,7 @@ export const config: TriggerConfig = {
   project: "${projectRef}",
   logLevel: "log",
   retries: {
-    enabledInDev: false,
+    enabledInDev: true,
     default: {
       maxAttempts: 3,
       minTimeoutInMs: 1000,