Executive Summary

PyjamaHR enables you to send automated and personalized emails to candidates throughout your hiring process. However, sometimes emails marked as "sent" in PyjamaHR do not reach the recipient or fail to appear in your Sent folder. This article provides a comprehensive, actionable guide to diagnosing and resolving email delivery issues, based on real customer scenarios and the latest platform workflows.

Detailed Overview

What Is the Issue?

Customers report that emails sent from PyjamaHR:
- Are marked as "sent" in the platform but are not received by candidates.
- Do not appear in the sender’s Sent folder (Gmail, Outlook, custom SMTP).
- Sometimes only a portion of candidates receive emails (e.g., 30-40% delivery).
- Replies from candidates are not received or do not appear in PyjamaHR.
- Bulk emails or high-volume sends can trigger integration disconnects.

Why Does This Matter?

Effective communication with candidates is critical for a smooth hiring process. Missed emails can result in lost candidates, poor candidate experience, and increased manual work for recruiters.

How PyjamaHR Handles Email

Default Sending: If no email is integrated, PyjamaHR sends emails via its internal system (e.g., [email protected]).
Custom Integration: You can integrate your work email (Gmail, Outlook, custom SMTP) for better deliverability, branding, and tracking.
Email History: Sent emails should appear in the candidate’s mail history and, if integrated, in your own Sent folder.
Bulk Sending: Large batches may trigger provider limits or integration disconnects.

Step-by-Step Troubleshooting Guide

Prerequisites

Access to PyjamaHR with admin or recruiter permissions.
Access to your email account (Gmail, Outlook, or custom provider).
Candidate email addresses and job IDs for reference.

1. Check Email Integration Status

A. In PyjamaHR:
1. Go to Settings > Email.
2. Verify if your work email is integrated (shows as "Connected").
- If not, click Integrate Email and follow the prompts.
- For Gmail: Use OAuth login.
- For custom SMTP: Enter SMTP host, port, username, and password.

B. Common Issues:
- Integration can disconnect automatically (token expiry, provider security).
- After bulk sends, integration may revert to PyjamaHR’s internal email.

Screenshot Callout: Show the Settings > Email screen with integration status.

2. Test Email Delivery

Send a test email to your own address or a colleague via PyjamaHR.
Check:
- Does the recipient receive the email?
- Does it appear in your Sent folder (if integrated)?
- Does it show in the candidate’s mail history in PyjamaHR?

If not delivered:
- Check spam/junk folders.
- Confirm the recipient’s email address is correct.

3. Review Bulk Sending Limits

If sending to many candidates at once, some providers (especially Gmail, Outlook, custom SMTP) may throttle or block emails.
After a certain threshold (e.g., 10-20 emails), integration may disconnect and PyjamaHR will switch to its internal sender.
Re-authenticate your email integration if prompted.

Tip: For high-volume sends, stagger emails or use a dedicated work email with higher sending limits.

4. Check for Error Messages or Warnings

Look for any error banners in PyjamaHR after sending emails.
If you see "Authentication failed" or "Configuration switched back to PyjamaHR," re-integrate your email.
For custom SMTP, verify credentials (host, port, username, password).

5. Verify Email History and Sent Folder

In PyjamaHR, open the candidate profile and check the Mail tab for sent emails.
In your email provider (Gmail, Outlook), check the Sent folder.
If emails are missing from both, integration may have failed or disconnected.

6. Check Candidate Feedback

If candidates report not receiving emails, ask for screenshots or confirmation of their inbox/spam folders.
Collect affected candidate email addresses and job IDs for support escalation.

7. Review Notification Settings

PyjamaHR sends application confirmation and other notifications by default.
If you want to disable automatic notifications, contact support (this must be done by PyjamaHR staff).

8. Escalate to Support (If Needed)

Gather:
Candidate email addresses and job IDs.
Screenshots of your integration settings.
Details of when and how the issue occurred.
Contact PyjamaHR support via chat or email with this information.

Advanced Usage & Best Practices

Power User Tips

Always integrate your work email for best deliverability and tracking.
Monitor integration status after bulk sends—re-authenticate promptly if disconnected.
Use unique sender addresses for each recruiter to avoid throttling.
Regularly test by sending emails to yourself or a test candidate.
Check Mailgun logs (if available via support) for delivery confirmation.

Do’s and Don’ts

Do:
- Reconnect your email integration if prompted.
- Use strong, unique passwords for custom SMTP.
- Check both PyjamaHR and your email provider’s Sent folders.

Don’t:
- Ignore integration warnings or repeated disconnects.
- Use free/public email providers for high-volume sending.
- Rely solely on PyjamaHR’s internal sender for bulk or critical emails.

Troubleshooting & Common Issues

1. Emails Not Delivered to Candidates

Possible Causes: Integration disconnected, provider throttling, incorrect recipient address, spam filtering.
Solution: Re-integrate email, verify credentials, check spam, stagger bulk sends.

2. Emails Not Appearing in Sent Folder

Possible Causes: Not using integrated email, integration disconnected mid-send.
Solution: Integrate your work email, re-authenticate if disconnected.

3. Only Some Candidates Receive Emails

Possible Causes: Provider limits, spam filtering, invalid addresses.
Solution: Check bounce reports (via support), verify addresses, stagger sends.

4. Replies from Candidates Not Received

Possible Causes: Notification settings, integration not set up, reply-to address misconfigured.
Solution: Ensure correct integration, check notification settings, contact support if replies are missing.

5. Authentication Failed on Custom SMTP

Possible Causes: Incorrect credentials, port, or host.
Solution: Double-check SMTP settings, share screenshots with support if needed.

6. Emails Going to Promotions/Spam

Possible Causes: Sending from generic or new domains, lack of integration, email content.
Solution: Integrate your work email, personalize content, ask recipients to whitelist your address.

7. Bulk Sending Switches to PyjamaHR Internal Email

Possible Causes: Provider limits reached, token expiry.
Solution: Monitor integration status, re-authenticate, consider using a dedicated email for bulk sends.

8. No Confirmation Emails Sent to Applicants

Possible Causes: Integration not set up, notifications disabled.
Solution: Integrate your email, contact support to adjust notification settings.

Comprehensive FAQ

1. Why are my emails marked as sent in PyjamaHR but not received by candidates?
Integration may have disconnected, or emails may be filtered as spam. Re-integrate your email and ask candidates to check spam folders.

2. Why don’t my sent emails appear in my Gmail/Outlook Sent folder?
Only emails sent via an integrated account appear in your Sent folder. If integration disconnects, PyjamaHR sends via its internal system, which won’t show in your Sent folder.

3. Why do only some candidates receive my emails?
You may have hit provider sending limits, or some addresses may be invalid. Stagger sends and verify addresses.

4. Why do replies from candidates not show up in PyjamaHR?
Replies are sent to your registered email if integrated. If not, check your email provider’s inbox and spam folders.

5. How do I re-integrate my email if it disconnects?
Go to Settings > Email, click "Integrate Email," and follow the prompts.

6. What should I do if I get an "Authentication failed" error?
Double-check your SMTP credentials (host, port, username, password). Share a screenshot with support if the issue persists.

7. Can I disable automatic confirmation emails to applicants?
Yes, but only PyjamaHR support can do this. Contact support to request this change.

8. Why do emails go to the Promotions or Spam folder?
This is determined by the recipient’s email provider. Integrating your work email and personalizing content can help.

9. What happens if I send too many emails at once?
Your provider may throttle or block further sends, and PyjamaHR may switch to its internal sender. Stagger bulk sends and monitor integration status.

10. How can I track email delivery status?
Check the candidate’s mail history in PyjamaHR and your Sent folder (if integrated). For advanced tracking, contact support for Mailgun logs.

11. Why did my email integration switch back to PyjamaHR’s internal email?
This can happen after bulk sends or token expiry. Re-integrate your email to restore functionality.

12. How do I get notified if my integration disconnects?
Currently, you must check integration status manually. If you notice emails not appearing in your Sent folder, re-authenticate promptly.

13. Can I use any email provider for integration?
Yes, as long as you have SMTP details. Some providers may have stricter limits or security checks.

14. What information should I provide to support for unresolved issues?
Candidate email addresses, job IDs, screenshots of your integration settings, and a description of the issue.

Email Integration: How to Integrate Gmail for Emails
Bulk Emailing: Best practices for mass communication.
Candidate Communication Tracking: Using the Mail tab in candidate profiles.
Notification Settings: Customizing automatic emails (contact support).
Job Board Integrations: Ensure jobs are published for maximum candidate reach.

Recommended Next Steps:
- Regularly review your email integration status.
- Test email delivery after any changes.
- Train your team on best practices for bulk sending.
- Contact support proactively with detailed information if issues persist.

Still having trouble?
If you’ve followed all troubleshooting steps and emails are still not delivered, please contact PyjamaHR support with detailed information for priority assistance.

Your feedback helps us improve!
If you have suggestions for this guide or need further help, please reach out to [email protected].

Troubleshooting E-mails Sent but Not Delivered in PyjamaHR: Step-by-Step Guide