diff --git a/packages/server/src/api/controllers/deploy/index.ts b/packages/server/src/api/controllers/deploy/index.ts
index 5d4603b864..6ef4c8f6fc 100644
--- a/packages/server/src/api/controllers/deploy/index.ts
+++ b/packages/server/src/api/controllers/deploy/index.ts
@@ -16,6 +16,7 @@ import {
   UserCtx,
   DeploymentStatus,
   DeploymentProgressResponse,
+  Automation,
 } from "@budibase/types"
 import sdk from "../../../sdk"
 import { builderSocket } from "../../../websockets"
@@ -76,17 +77,24 @@ async function initDeployedApp(prodAppId: any) {
   const db = context.getProdAppDB()
   console.log("Reading automation docs")
   const automations = (
-    await db.allDocs(
+    await db.allDocs<Automation>(
       getAutomationParams(null, {
         include_docs: true,
       })
     )
-  ).rows.map((row: any) => row.doc)
+  ).rows.map(row => row.doc!)
   await clearMetadata()
   const { count } = await disableAllCrons(prodAppId)
   const promises = []
   for (let automation of automations) {
-    promises.push(enableCronTrigger(prodAppId, automation))
+    promises.push(
+      enableCronTrigger(prodAppId, automation).catch(err => {
+        throw new Error(
+          `Failed to enable CRON trigger for automation "${automation.name}": ${err.message}`,
+          { cause: err }
+        )
+      })
+    )
   }
   const results = await Promise.all(promises)
   const enabledCount = results
diff --git a/packages/server/src/automations/utils.ts b/packages/server/src/automations/utils.ts
index 1fa346be19..f0492c79d8 100644
--- a/packages/server/src/automations/utils.ts
+++ b/packages/server/src/automations/utils.ts
@@ -182,7 +182,7 @@ export async function enableCronTrigger(appId: any, automation: Automation) {
     !automation.disabled
   ) {
     const inputs = trigger.inputs as CronTriggerInputs
-    const cronExp = inputs.cron
+    const cronExp = inputs.cron || ""
     const validation = helpers.cron.validate(cronExp)
     if (!validation.valid) {
       throw new Error(