diff --git a/packages/backend-core/src/queue/inMemoryQueue.ts b/packages/backend-core/src/queue/inMemoryQueue.ts
index 867388ae07..842d3243bc 100644
--- a/packages/backend-core/src/queue/inMemoryQueue.ts
+++ b/packages/backend-core/src/queue/inMemoryQueue.ts
@@ -3,6 +3,7 @@ import { newid } from "../utils"
 import { Queue, QueueOptions, JobOptions } from "./queue"
 import { helpers } from "@budibase/shared-core"
 import { Job, JobId, JobInformation } from "bull"
+import { cloneDeep } from "lodash"
 
 function jobToJobInformation(job: Job): JobInformation {
   let cron = ""
@@ -33,12 +34,13 @@ function jobToJobInformation(job: Job): JobInformation {
   }
 }
 
-interface JobMessage<T = any> extends Partial<Job<T>> {
+export interface TestQueueMessage<T = any> extends Partial<Job<T>> {
   id: string
   timestamp: number
   queue: Queue<T>
   data: any
   opts?: JobOptions
+  manualTrigger?: boolean
 }
 
 /**
@@ -47,12 +49,16 @@ interface JobMessage<T = any> extends Partial<Job<T>> {
  * internally to register when messages are available to the consumers - in can
  * support many inputs and many consumers.
  */
-class InMemoryQueue implements Partial<Queue> {
+export class InMemoryQueue<T = any> implements Partial<Queue<T>> {
   _name: string
   _opts?: QueueOptions
-  _messages: JobMessage[]
+  _messages: TestQueueMessage<T>[]
   _queuedJobIds: Set<string>
-  _emitter: NodeJS.EventEmitter<{ message: [JobMessage]; completed: [Job] }>
+  _emitter: NodeJS.EventEmitter<{
+    message: [TestQueueMessage<T>]
+    completed: [Job<T>]
+    removed: [TestQueueMessage<T>]
+  }>
   _runCount: number
   _addCount: number
 
@@ -82,7 +88,15 @@ class InMemoryQueue implements Partial<Queue> {
    */
   async process(concurrencyOrFunc: number | any, func?: any) {
     func = typeof concurrencyOrFunc === "number" ? func : concurrencyOrFunc
-    this._emitter.on("message", async message => {
+    this._emitter.on("message", async msg => {
+      const message = cloneDeep(msg)
+
+      // For the purpose of testing, don't trigger cron jobs immediately.
+      // Require the test to trigger them manually with timestamps.
+      if (!message.manualTrigger && message.opts?.repeat != null) {
+        return
+      }
+
       let resp = func(message)
 
       async function retryFunc(fnc: any) {
@@ -97,7 +111,7 @@ class InMemoryQueue implements Partial<Queue> {
       if (resp.then != null) {
         try {
           await retryFunc(resp)
-          this._emitter.emit("completed", message as Job)
+          this._emitter.emit("completed", message as Job<T>)
         } catch (e: any) {
           console.error(e)
         }
@@ -114,7 +128,6 @@ class InMemoryQueue implements Partial<Queue> {
     return this as any
   }
 
-  // simply puts a message to the queue and emits to the queue for processing
   /**
    * Simple function to replicate the add message functionality of Bull, putting
    * a new message on the queue. This then emits an event which will be used to
@@ -123,7 +136,13 @@ class InMemoryQueue implements Partial<Queue> {
    * a JSON message as this is required by Bull.
    * @param repeat serves no purpose for the import queue.
    */
-  async add(data: any, opts?: JobOptions) {
+  async add(data: T | string, optsOrT?: JobOptions | T) {
+    if (typeof data === "string") {
+      throw new Error("doesn't support named jobs")
+    }
+
+    const opts = optsOrT as JobOptions
+
     const jobId = opts?.jobId?.toString()
     if (jobId && this._queuedJobIds.has(jobId)) {
       console.log(`Ignoring already queued job ${jobId}`)
@@ -138,7 +157,7 @@ class InMemoryQueue implements Partial<Queue> {
     }
 
     const pushMessage = () => {
-      const message: JobMessage = {
+      const message: TestQueueMessage = {
         id: newid(),
         timestamp: Date.now(),
         queue: this as unknown as Queue,
@@ -164,13 +183,14 @@ class InMemoryQueue implements Partial<Queue> {
    */
   async close() {}
 
-  /**
-   * This removes a cron which has been implemented, this is part of Bull API.
-   * @param cronJobId The cron which is to be removed.
-   */
-  async removeRepeatableByKey(cronJobId: string) {
-    // TODO: implement for testing
-    console.log(cronJobId)
+  async removeRepeatableByKey(id: string) {
+    for (const [idx, message] of this._messages.entries()) {
+      if (message.id === id) {
+        this._messages.splice(idx, 1)
+        this._emitter.emit("removed", message)
+        return
+      }
+    }
   }
 
   async removeJobs(_pattern: string) {
@@ -193,6 +213,16 @@ class InMemoryQueue implements Partial<Queue> {
     return null
   }
 
+  manualTrigger(id: JobId) {
+    for (const message of this._messages) {
+      if (message.id === id) {
+        this._emitter.emit("message", { ...message, manualTrigger: true })
+        return
+      }
+    }
+    throw new Error(`Job with id ${id} not found`)
+  }
+
   on(event: string, callback: (...args: any[]) => void): Queue {
     // @ts-expect-error - this callback can be one of many types
     this._emitter.on(event, callback)
@@ -214,7 +244,9 @@ class InMemoryQueue implements Partial<Queue> {
   }
 
   async getRepeatableJobs() {
-    return this._messages.map(job => jobToJobInformation(job as Job))
+    return this._messages
+      .filter(job => job.opts?.repeat != null)
+      .map(job => jobToJobInformation(job as Job))
   }
 }
 
diff --git a/packages/backend-core/src/queue/index.ts b/packages/backend-core/src/queue/index.ts
index b7d565ba13..5603c40513 100644
--- a/packages/backend-core/src/queue/index.ts
+++ b/packages/backend-core/src/queue/index.ts
@@ -1,2 +1,3 @@
 export * from "./queue"
 export * from "./constants"
+export * from "./inMemoryQueue"
diff --git a/packages/server/src/automations/logging/index.ts b/packages/server/src/automations/logging/index.ts
index 9d16f15a67..ed8dd9db88 100644
--- a/packages/server/src/automations/logging/index.ts
+++ b/packages/server/src/automations/logging/index.ts
@@ -1,7 +1,7 @@
 import env from "../../environment"
 import { AutomationResults, Automation, App } from "@budibase/types"
 import { automations } from "@budibase/pro"
-import { db as dbUtils } from "@budibase/backend-core"
+import { db as dbUtils, logging } from "@budibase/backend-core"
 import sizeof from "object-sizeof"
 
 const MAX_LOG_SIZE_MB = 5
@@ -32,7 +32,16 @@ export async function storeLog(
   if (bytes / MB_IN_BYTES > MAX_LOG_SIZE_MB) {
     sanitiseResults(results)
   }
-  await automations.logs.storeLog(automation, results)
+  try {
+    await automations.logs.storeLog(automation, results)
+  } catch (e: any) {
+    if (e.status === 413 && e.request?.data) {
+      // if content is too large we shouldn't log it
+      delete e.request.data
+      e.request.data = { message: "removed due to large size" }
+    }
+    logging.logAlert("Error writing automation log", e)
+  }
 }
 
 export async function checkAppMetadata(apps: App[]) {
diff --git a/packages/server/src/automations/tests/steps/cron-automations.spec.ts b/packages/server/src/automations/tests/steps/cron-automations.spec.ts
deleted file mode 100644
index 41de957c52..0000000000
--- a/packages/server/src/automations/tests/steps/cron-automations.spec.ts
+++ /dev/null
@@ -1,45 +0,0 @@
-import tk from "timekeeper"
-import "../../../environment"
-import * as automations from "../../index"
-import TestConfiguration from "../../../tests/utilities/TestConfiguration"
-import { createAutomationBuilder } from "../utilities/AutomationTestBuilder"
-
-const initialTime = Date.now()
-tk.freeze(initialTime)
-
-const oneMinuteInMs = 60 * 1000
-
-describe("cron automations", () => {
-  const config = new TestConfiguration()
-
-  beforeAll(async () => {
-    await automations.init()
-    await config.init()
-  })
-
-  afterAll(async () => {
-    await automations.shutdown()
-    config.end()
-  })
-
-  beforeEach(() => {
-    tk.freeze(initialTime)
-  })
-
-  it("should initialise the automation timestamp", async () => {
-    await createAutomationBuilder(config).onCron({ cron: "* * * * *" }).save()
-
-    tk.travel(Date.now() + oneMinuteInMs)
-    await config.publish()
-
-    const { data } = await config.getAutomationLogs()
-    expect(data).toHaveLength(1)
-    expect(data).toEqual([
-      expect.objectContaining({
-        trigger: expect.objectContaining({
-          outputs: { timestamp: initialTime + oneMinuteInMs },
-        }),
-      }),
-    ])
-  })
-})
diff --git a/packages/server/src/automations/tests/steps/loop.spec.ts b/packages/server/src/automations/tests/steps/loop.spec.ts
index f8af7dcf9f..88e641f5ff 100644
--- a/packages/server/src/automations/tests/steps/loop.spec.ts
+++ b/packages/server/src/automations/tests/steps/loop.spec.ts
@@ -21,6 +21,11 @@ describe("Attempt to run a basic loop automation", () => {
   })
 
   beforeEach(async () => {
+    const { automations } = await config.api.automation.fetch()
+    for (const automation of automations) {
+      await config.api.automation.delete(automation)
+    }
+
     table = await config.api.table.save(basicTable())
     await config.api.row.save(table._id!, {})
   })
diff --git a/packages/server/src/automations/tests/triggers/cron.spec.ts b/packages/server/src/automations/tests/triggers/cron.spec.ts
index 3bbbbf0b0b..90d29a60c1 100644
--- a/packages/server/src/automations/tests/triggers/cron.spec.ts
+++ b/packages/server/src/automations/tests/triggers/cron.spec.ts
@@ -1,6 +1,15 @@
 import { createAutomationBuilder } from "../utilities/AutomationTestBuilder"
 import TestConfiguration from "../../../tests/utilities/TestConfiguration"
-import { captureAutomationResults } from "../utilities"
+import {
+  captureAutomationMessages,
+  captureAutomationRemovals,
+  captureAutomationResults,
+  triggerCron,
+} from "../utilities"
+import { automations } from "@budibase/pro"
+import { AutomationData, AutomationStatus } from "@budibase/types"
+import { MAX_AUTOMATION_RECURRING_ERRORS } from "../../../constants"
+import { queue } from "@budibase/backend-core"
 
 describe("cron trigger", () => {
   const config = new TestConfiguration()
@@ -13,6 +22,13 @@ describe("cron trigger", () => {
     config.end()
   })
 
+  beforeEach(async () => {
+    const { automations } = await config.api.automation.fetch()
+    for (const automation of automations) {
+      await config.api.automation.delete(automation)
+    }
+  })
+
   it("should queue a Bull cron job", async () => {
     const { automation } = await createAutomationBuilder(config)
       .onCron({ cron: "* * * * *" })
@@ -21,12 +37,12 @@ describe("cron trigger", () => {
       })
       .save()
 
-    const jobs = await captureAutomationResults(automation, () =>
+    const messages = await captureAutomationMessages(automation, () =>
       config.api.application.publish()
     )
-    expect(jobs).toHaveLength(1)
+    expect(messages).toHaveLength(1)
 
-    const repeat = jobs[0].opts?.repeat
+    const repeat = messages[0].opts?.repeat
     if (!repeat || !("cron" in repeat)) {
       throw new Error("Expected cron repeat")
     }
@@ -49,4 +65,85 @@ describe("cron trigger", () => {
       },
     })
   })
+
+  it("should stop if the job fails more than 3 times", async () => {
+    const { automation } = await createAutomationBuilder(config)
+      .onCron({ cron: "* * * * *" })
+      .queryRows({
+        // @ts-expect-error intentionally sending invalid data
+        tableId: null,
+      })
+      .save()
+
+    const [message] = await captureAutomationMessages(automation, () =>
+      config.api.application.publish()
+    )
+
+    await config.withProdApp(async () => {
+      let results: queue.TestQueueMessage<AutomationData>[] = []
+      const removed = await captureAutomationRemovals(automation, async () => {
+        results = await captureAutomationResults(automation, async () => {
+          for (let i = 0; i < MAX_AUTOMATION_RECURRING_ERRORS; i++) {
+            triggerCron(message)
+          }
+        })
+      })
+
+      expect(removed).toHaveLength(1)
+      expect(removed[0].id).toEqual(message.id)
+
+      expect(results).toHaveLength(5)
+
+      const search = await automations.logs.logSearch({
+        automationId: automation._id,
+        status: AutomationStatus.STOPPED_ERROR,
+      })
+      expect(search.data).toHaveLength(1)
+      expect(search.data[0].status).toEqual(AutomationStatus.STOPPED_ERROR)
+    })
+  })
+
+  it("should fill in the timestamp if one is not provided", async () => {
+    const runner = await createAutomationBuilder(config)
+      .onCron({ cron: "* * * * *" })
+      .serverLog({
+        text: "Hello, world!",
+      })
+      .save()
+
+    await config.api.application.publish()
+
+    const results = await captureAutomationResults(
+      runner.automation,
+      async () => {
+        await runner.trigger({ timeout: 1000, fields: {} })
+      }
+    )
+    expect(results).toHaveLength(1)
+    expect(results[0].data.event.timestamp).toBeWithin(
+      Date.now() - 1000,
+      Date.now() + 1000
+    )
+  })
+
+  it("should use the given timestamp if one is given", async () => {
+    const timestamp = 1234
+    const runner = await createAutomationBuilder(config)
+      .onCron({ cron: "* * * * *" })
+      .serverLog({
+        text: "Hello, world!",
+      })
+      .save()
+
+    await config.api.application.publish()
+
+    const results = await captureAutomationResults(
+      runner.automation,
+      async () => {
+        await runner.trigger({ timeout: 1000, fields: {}, timestamp })
+      }
+    )
+    expect(results).toHaveLength(1)
+    expect(results[0].data.event.timestamp).toEqual(timestamp)
+  })
 })
diff --git a/packages/server/src/automations/tests/utilities/AutomationTestBuilder.ts b/packages/server/src/automations/tests/utilities/AutomationTestBuilder.ts
index d707430a35..a95e58f69d 100644
--- a/packages/server/src/automations/tests/utilities/AutomationTestBuilder.ts
+++ b/packages/server/src/automations/tests/utilities/AutomationTestBuilder.ts
@@ -220,10 +220,34 @@ class AutomationRunner<TStep extends AutomationTriggerStepId> {
   async trigger(
     request: TriggerAutomationRequest
   ): Promise<TriggerAutomationResponse> {
-    return await this.config.api.automation.trigger(
-      this.automation._id!,
-      request
-    )
+    if (!this.config.prodAppId) {
+      throw new Error(
+        "Automations can only be triggered in a production app context, call config.api.application.publish()"
+      )
+    }
+    // Because you can only trigger automations in a production app context, we
+    // wrap the trigger call to make tests a bit cleaner. If you really want to
+    // test triggering an automation in a dev app context, you can use the
+    // automation API directly.
+    return await this.config.withProdApp(async () => {
+      try {
+        return await this.config.api.automation.trigger(
+          this.automation._id!,
+          request
+        )
+      } catch (e: any) {
+        if (e.cause.status === 404) {
+          throw new Error(
+            `Automation with ID ${
+              this.automation._id
+            } not found in app ${this.config.getAppId()}. You may have forgotten to call config.api.application.publish().`,
+            { cause: e }
+          )
+        } else {
+          throw e
+        }
+      }
+    })
   }
 }
 
diff --git a/packages/server/src/automations/tests/utilities/index.ts b/packages/server/src/automations/tests/utilities/index.ts
index 44f6d3b8ca..4b41f1d977 100644
--- a/packages/server/src/automations/tests/utilities/index.ts
+++ b/packages/server/src/automations/tests/utilities/index.ts
@@ -6,6 +6,7 @@ import { Knex } from "knex"
 import { getQueue } from "../.."
 import { Job } from "bull"
 import { helpers } from "@budibase/shared-core"
+import { queue } from "@budibase/backend-core"
 
 let config: TestConfiguration
 
@@ -20,6 +21,17 @@ export function afterAll() {
   config.end()
 }
 
+export function getTestQueue(): queue.InMemoryQueue<AutomationData> {
+  return getQueue() as unknown as queue.InMemoryQueue<AutomationData>
+}
+
+export function triggerCron(message: Job<AutomationData>) {
+  if (!message.opts?.repeat || !("cron" in message.opts.repeat)) {
+    throw new Error("Expected cron message")
+  }
+  getTestQueue().manualTrigger(message.id)
+}
+
 export async function runInProd(fn: any) {
   env._set("NODE_ENV", "production")
   let error
@@ -34,23 +46,99 @@ export async function runInProd(fn: any) {
   }
 }
 
+export async function captureAllAutomationRemovals(f: () => Promise<unknown>) {
+  const messages: Job<AutomationData>[] = []
+  const queue = getQueue()
+
+  const messageListener = async (message: Job<AutomationData>) => {
+    messages.push(message)
+  }
+
+  queue.on("removed", messageListener)
+  try {
+    await f()
+    // Queue messages tend to be send asynchronously in API handlers, so there's
+    // no guarantee that awaiting this function will have queued anything yet.
+    // We wait here to make sure we're queued _after_ any existing async work.
+    await helpers.wait(100)
+  } finally {
+    queue.off("removed", messageListener)
+  }
+
+  return messages
+}
+
+export async function captureAutomationRemovals(
+  automation: Automation | string,
+  f: () => Promise<unknown>
+) {
+  const messages = await captureAllAutomationRemovals(f)
+  return messages.filter(
+    m =>
+      m.data.automation._id ===
+      (typeof automation === "string" ? automation : automation._id)
+  )
+}
+
+export async function captureAllAutomationMessages(f: () => Promise<unknown>) {
+  const messages: Job<AutomationData>[] = []
+  const queue = getQueue()
+
+  const messageListener = async (message: Job<AutomationData>) => {
+    messages.push(message)
+  }
+
+  queue.on("message", messageListener)
+  try {
+    await f()
+    // Queue messages tend to be send asynchronously in API handlers, so there's
+    // no guarantee that awaiting this function will have queued anything yet.
+    // We wait here to make sure we're queued _after_ any existing async work.
+    await helpers.wait(100)
+  } finally {
+    queue.off("message", messageListener)
+  }
+
+  return messages
+}
+
+export async function captureAutomationMessages(
+  automation: Automation | string,
+  f: () => Promise<unknown>
+) {
+  const messages = await captureAllAutomationMessages(f)
+  return messages.filter(
+    m =>
+      m.data.automation._id ===
+      (typeof automation === "string" ? automation : automation._id)
+  )
+}
+
 /**
  * Capture all automation runs that occur during the execution of a function.
  * This function will wait for all messages to be processed before returning.
  */
 export async function captureAllAutomationResults(
   f: () => Promise<unknown>
-): Promise<Job<AutomationData>[]> {
-  const runs: Job<AutomationData>[] = []
+): Promise<queue.TestQueueMessage<AutomationData>[]> {
+  const runs: queue.TestQueueMessage<AutomationData>[] = []
   const queue = getQueue()
-  let messagesReceived = 0
+  let messagesOutstanding = 0
 
-  const completedListener = async (job: Job<AutomationData>) => {
+  const completedListener = async (
+    job: queue.TestQueueMessage<AutomationData>
+  ) => {
     runs.push(job)
-    messagesReceived--
+    messagesOutstanding--
   }
-  const messageListener = async () => {
-    messagesReceived++
+  const messageListener = async (
+    message: queue.TestQueueMessage<AutomationData>
+  ) => {
+    // Don't count cron messages, as they don't get triggered automatically.
+    if (!message.manualTrigger && message.opts?.repeat != null) {
+      return
+    }
+    messagesOutstanding++
   }
   queue.on("message", messageListener)
   queue.on("completed", completedListener)
@@ -61,9 +149,18 @@ export async function captureAllAutomationResults(
     // We wait here to make sure we're queued _after_ any existing async work.
     await helpers.wait(100)
   } finally {
+    const waitMax = 10000
+    let waited = 0
     // eslint-disable-next-line no-unmodified-loop-condition
-    while (messagesReceived > 0) {
+    while (messagesOutstanding > 0) {
       await helpers.wait(50)
+      waited += 50
+      if (waited > waitMax) {
+        // eslint-disable-next-line no-unsafe-finally
+        throw new Error(
+          `Timed out waiting for automation runs to complete. ${messagesOutstanding} messages waiting for completion.`
+        )
+      }
     }
     queue.off("completed", completedListener)
     queue.off("message", messageListener)
diff --git a/packages/server/src/automations/utils.ts b/packages/server/src/automations/utils.ts
index 83665fc975..9af166bcf9 100644
--- a/packages/server/src/automations/utils.ts
+++ b/packages/server/src/automations/utils.ts
@@ -72,7 +72,7 @@ export async function processEvent(job: AutomationJob) {
 
       const task = async () => {
         try {
-          if (isCronTrigger(job.data.automation)) {
+          if (isCronTrigger(job.data.automation) && !job.data.event.timestamp) {
             // Requires the timestamp at run time
             job.data.event.timestamp = Date.now()
           }
diff --git a/packages/server/src/tests/utilities/TestConfiguration.ts b/packages/server/src/tests/utilities/TestConfiguration.ts
index 1f464b2ea4..edb397169d 100644
--- a/packages/server/src/tests/utilities/TestConfiguration.ts
+++ b/packages/server/src/tests/utilities/TestConfiguration.ts
@@ -261,11 +261,13 @@ export default class TestConfiguration {
   async withApp<R>(app: App | string, f: () => Promise<R>) {
     const oldAppId = this.appId
     this.appId = typeof app === "string" ? app : app.appId
-    try {
-      return await f()
-    } finally {
-      this.appId = oldAppId
-    }
+    return await context.doInAppContext(this.appId, async () => {
+      try {
+        return await f()
+      } finally {
+        this.appId = oldAppId
+      }
+    })
   }
 
   async withProdApp<R>(f: () => Promise<R>) {
diff --git a/packages/server/src/threads/automation.ts b/packages/server/src/threads/automation.ts
index 174efa0fe0..f854635559 100644
--- a/packages/server/src/threads/automation.ts
+++ b/packages/server/src/threads/automation.ts
@@ -155,23 +155,12 @@ class Orchestrator {
     return step
   }
 
-  async getMetadata(): Promise<AutomationMetadata> {
-    const metadataId = generateAutomationMetadataID(this.automation._id!)
-    const db = context.getAppDB()
-    let metadata: AutomationMetadata
-    try {
-      metadata = await db.get(metadataId)
-    } catch (err) {
-      metadata = {
-        _id: metadataId,
-        errorCount: 0,
-      }
-    }
-    return metadata
+  isCron(): boolean {
+    return isRecurring(this.automation)
   }
 
   async stopCron(reason: string) {
-    if (!this.job.opts.repeat) {
+    if (!this.isCron()) {
       return
     }
     logging.logWarn(
@@ -192,45 +181,37 @@ class Orchestrator {
     await storeLog(automation, this.executionOutput)
   }
 
-  async checkIfShouldStop(metadata: AutomationMetadata): Promise<boolean> {
-    if (!metadata.errorCount || !this.job.opts.repeat) {
-      return false
-    }
-    if (metadata.errorCount >= MAX_AUTOMATION_RECURRING_ERRORS) {
-      await this.stopCron("errors")
-      return true
-    }
-    return false
+  async getMetadata(): Promise<AutomationMetadata> {
+    const metadataId = generateAutomationMetadataID(this.automation._id!)
+    const db = context.getAppDB()
+    const metadata = await db.tryGet<AutomationMetadata>(metadataId)
+    return metadata || { _id: metadataId, errorCount: 0 }
   }
 
-  async updateMetadata(metadata: AutomationMetadata) {
-    const output = this.executionOutput,
-      automation = this.automation
-    if (!output || !isRecurring(automation)) {
-      return
-    }
-    const count = metadata.errorCount
-    const isError = isErrorInOutput(output)
-    // nothing to do in this scenario, escape
-    if (!count && !isError) {
-      return
-    }
-    if (isError) {
-      metadata.errorCount = count ? count + 1 : 1
-    } else {
-      metadata.errorCount = 0
-    }
+  async incrementErrorCount() {
     const db = context.getAppDB()
-    try {
-      await db.put(metadata)
-    } catch (err) {
-      logging.logAlertWithInfo(
-        "Failed to write automation metadata",
-        db.name,
-        automation._id!,
-        err
-      )
+    let err: Error | undefined = undefined
+    for (let attempt = 0; attempt < 10; attempt++) {
+      const metadata = await this.getMetadata()
+      metadata.errorCount ||= 0
+      metadata.errorCount++
+
+      try {
+        await db.put(metadata)
+        return metadata.errorCount
+      } catch (error: any) {
+        err = error
+        await helpers.wait(1000 + Math.random() * 1000)
+      }
     }
+
+    logging.logAlertWithInfo(
+      "Failed to update error count in automation metadata",
+      db.name,
+      this.automation._id!,
+      err
+    )
+    return undefined
   }
 
   updateExecutionOutput(id: string, stepId: string, inputs: any, outputs: any) {
@@ -293,18 +274,6 @@ class Orchestrator {
         await enrichBaseContext(this.context)
         this.context.user = this.currentUser
 
-        let metadata
-
-        // check if this is a recurring automation,
-        if (isProdAppID(this.appId) && isRecurring(this.automation)) {
-          span?.addTags({ recurring: true })
-          metadata = await this.getMetadata()
-          const shouldStop = await this.checkIfShouldStop(metadata)
-          if (shouldStop) {
-            span?.addTags({ shouldStop: true })
-            return
-          }
-        }
         const start = performance.now()
 
         await this.executeSteps(this.automation.definition.steps)
@@ -320,23 +289,22 @@ class Orchestrator {
           }
         )
 
-        try {
-          await storeLog(this.automation, this.executionOutput)
-        } catch (e: any) {
-          if (e.status === 413 && e.request?.data) {
-            // if content is too large we shouldn't log it
-            delete e.request.data
-            e.request.data = { message: "removed due to large size" }
-          }
-          logging.logAlert("Error writing automation log", e)
-        }
+        let errorCount = 0
         if (
           isProdAppID(this.appId) &&
-          isRecurring(this.automation) &&
-          metadata
+          this.isCron() &&
+          isErrorInOutput(this.executionOutput)
         ) {
-          await this.updateMetadata(metadata)
+          errorCount = (await this.incrementErrorCount()) || 0
         }
+
+        if (errorCount >= MAX_AUTOMATION_RECURRING_ERRORS) {
+          await this.stopCron("errors")
+          span?.addTags({ shouldStop: true })
+        } else {
+          await storeLog(this.automation, this.executionOutput)
+        }
+
         return this.executionOutput
       }
     )
@@ -763,7 +731,7 @@ export async function executeInThread(
   })) as AutomationResponse
 }
 
-export const removeStalled = async (job: Job) => {
+export const removeStalled = async (job: Job<AutomationData>) => {
   const appId = job.data.event.appId
   if (!appId) {
     throw new Error("Unable to execute, event doesn't contain app ID.")
diff --git a/packages/types/src/api/web/app/automation.ts b/packages/types/src/api/web/app/automation.ts
index f72966d100..6b6c63a261 100644
--- a/packages/types/src/api/web/app/automation.ts
+++ b/packages/types/src/api/web/app/automation.ts
@@ -65,6 +65,7 @@ export interface ClearAutomationLogResponse {
 
 export interface TriggerAutomationRequest {
   fields: Record<string, any>
+  timestamp?: number
   // time in seconds
   timeout: number
 }