Email Integration
Connect Gmail to Job Tracker and understand how Autopilot handles application emails and verification codes.
Last updated 19 days ago
Gmail integration is available to all Simplify users. Connect it from Settings → Email Integration to view recruiting conversations and approve suggested status updates in Job Tracker. Autopilot uses a separate email proxy on Letterfern, our partner domain, to handle supported application verification codes and forward application mail.
Gmail integration and the email proxy
We built Gmail integration because recruiting conversations often live apart from application records. Matching a conversation to its job lets you read it and decide what to do next without copying information between your inbox and tracker. The proxy solves a different task: receiving application mail and verification codes at the address used by Autopilot.
Connect Gmail
Open Settings and find Email Integration.
Choose Enable Email Integration.
Sign in to the Google account you want to connect and review the requested permissions.
Complete the connection and wait for the initial sync. Your connected Gmail address appears in Settings afterward.
The initial sync matches recruiting mail with your tracked applications and can take time. Use the account that receives the relevant conversations. Your connected Gmail address and the email on your Simplify account are separate settings.
View recruiting conversations
Open an application in Job Tracker.
Select Emails and browse the matched threads.
Open a thread to read it. You can archive conversations you no longer need visible.
Threads are shown with the most recent conversations first and marked read when opened. Matching depends on the email and application information, so do not assume every inbox message will appear under a tracked job.
Review suggested status updates
When a matched message suggests a change such as an interview invitation or rejection, Simplify can recommend a tracker status update. Choose Approve to apply it, Decline to dismiss it, or Approve All when you want to accept the pending suggestions.
A recommendation is a proposed change to your tracker, not a message sent to the recruiter. Read the email and verify the application before approving, especially if you have several roles at the same company.
Compose and send email
Open the tracked application’s Emails tab and choose Compose.
Enter the recipients and subject. Suggested contacts can come from conversations associated with that application.
Write your message, or use Ask AI with Simplify+ to generate a draft.
Review the recipients and final text, then choose Send.
You can minimize the compose window while referring to other application information. Generating a draft does not send it; sending is a separate action.
Generate a draft with Simplify+
In the compose window, choose Ask AI and describe the message or choose a template for your current stage:
Application: follow up or ask for a referral.
Assessment: request a deadline extension.
Interview: thank the interviewer, follow up, reschedule, or decline.
Offer: negotiate, accept, request more time, or decline.
No longer in consideration: send a final thank-you.
We grouped templates by stage so the draft starts with the right purpose. Add specific details such as a conversation topic or a deadline. Edit the draft before sending, and check any names, dates, compensation figures, and commitments.
How Autopilot handles one-time passwords
Some application systems email a one-time password (OTP), also called a verification or security code, before an application can continue. On supported applications, Simplify creates or reuses an email proxy and uses it as the application’s contact email.
The application system emails the code to the proxy.
Simplify receives the message and matches the code to the application.
Autopilot enters the code and continues the application automatically.
The proxy comes from Letterfern (letterfern.com), Simplify’s partner domain for job application emails. You may see the full address ending in @resend.letterfern.com on an application. That address belongs to this application email service; you do not need to replace your regular Simplify account email with it.
Where application mail goes
Regular messages sent to the proxy, such as application confirmations or recruiter correspondence, are forwarded to your current Simplify account email. Forwarded messages identify the original sender and direct replies to their reply address. Verification messages may be handled automatically without being forwarded.
Keep your Simplify account email up to date and check its inbox and spam folder for application mail. The proxy works without Gmail integration and can forward to a non-Gmail address. It is not a separate Gmail inbox you need to sign in to.
Automatic code handling depends on support for the application system and receipt of a usable code. If verification cannot be completed and the run fails, open the employer’s application and finish manually with Copilot.
Disconnect Gmail
Open Settings → Email Integration.
Choose Disable Email Integration and confirm. If a sync is running, wait for it to finish first.
This disconnects the Gmail integration. It does not disable Autopilot’s separate email proxy. Reconnecting Gmail starts a new initial sync.
If email is missing or the connection fails
Check the connected Gmail address in Settings and that the job is in your tracker. Allow the initial sync to finish and check the original inbox for the conversation. If a forwarded proxy message is missing, check the current email on your Simplify account and its spam folder instead.
For a persistent problem, contact support with the application and the affected connection or forwarding route. For how connected email data is processed, read the Privacy Policy.
Related articles
Was this helpful?
Still need help? Share an idea