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My Agent Platform

Email isn't syncing

If your agent can’t read your email, or only sees old emails, work through these in order.

1. Is the connection healthy?

Section titled “1. Is the connection healthy?”

The fastest way to check is to use the built-in health probe:

  1. Go to Settings → Integrations → Email.
  2. Find the inbox in the list — each row has a live status dot and a Check button.
  3. Click Check. The dashboard probes IMAP health against your provider in real time and reports one of: IMAP OK (green), auth_failed (red — password rotated or wrong), or an error string explaining a connection failure.

You can also ask your agent directly (“Can you read my inbox right now?”), but the status card is faster and more precise — it tells you the specific failure mode instead of a vague “I couldn’t reach it.”

2. Authentication errors

Section titled “2. Authentication errors”

The most common issue. Your app password isn’t working.

Why app passwords fail:

  • You generated a new one at your email provider and forgot to update it here
  • Your provider rotated / expired your app password
  • You pasted the password with spaces still in it (Gmail’s 16-character code has spaces when displayed but should be entered without spaces)
  • Your provider requires 2-factor authentication first — and you haven’t set it up yet

Fix (fastest path — use Reconnect, not Disconnect):

  1. Go to your provider’s security settings (Gmail: myaccount.google.com/apppasswords, iCloud: appleid.apple.com, etc.)
  2. Generate a NEW app password specifically labeled “My Agent Platform”
  3. Copy it without spaces
  4. In the dashboard, go to Settings → Integrations → Email, find the broken account, and click Reconnect. A password field appears inline — paste the new app password and confirm. This preserves all the stored metadata and skips the full add-account wizard.
  5. The status dot flips to IMAP OK within a few seconds.

If Reconnect refuses to save, fall back to Disconnect and then Add email account with the new password. This nukes the stored state and rebuilds it.

3. “Can’t reach server” errors

Section titled “3. “Can’t reach server” errors”

Means the IMAP server is unreachable from our infrastructure.

Possible causes:

  • Your email provider is down — check their status page
  • IMAP is disabled for your account — some corporate Google Workspace admins disable IMAP. Ask your IT.
  • IP-based blocking — rare, but some providers block connections from unfamiliar IP ranges. Reconnecting usually fixes this.

4. “Connected but not syncing”

Section titled “4. “Connected but not syncing””

If the status is green but your agent says “I don’t see any new emails”:

  • Give it 60 seconds. IMAP sync isn’t instant after a connection is established.
  • Try asking explicitly: “Check my inbox right now and tell me the 5 most recent emails.” This forces a fresh sync.
  • Check the email folder the agent is looking at. By default it reads INBOX. If your provider uses a different folder name (some Exchange servers use “Inbox” with capitalization or localized names), tell your agent explicitly: “Look in my ‘Correo’ folder.”

5. Specific provider issues

Section titled “5. Specific provider issues”

Gmail / Google Workspace

Section titled “Gmail / Google Workspace”
  • 2-Step Verification must be ON — required before you can generate an app password
  • “Less secure app access” was deprecated years ago and isn’t what you want. Always use app passwords.
  • Workspace admins can block IMAP — ask your admin if imap.gmail.com:993 is blocked for your domain

Outlook / Office 365

Section titled “Outlook / Office 365”
  • Modern Authentication (OAuth) is Microsoft’s preferred path, but it’s painful for third parties. We use app passwords via legacy authentication.
  • Your organization may have disabled legacy auth. If so, you’ll get “authentication failed” even with a correct app password. This is a Microsoft-side restriction.

iCloud

Section titled “iCloud”
  • You need Two-Factor Authentication on your Apple ID before app-specific passwords are even offered
  • Apple occasionally expires app-specific passwords without warning — just regenerate

Yahoo

Section titled “Yahoo”
  • Yahoo has been aggressive about disabling legacy IMAP access for old accounts. If your account was created before 2010, you may hit issues.
  • App passwords are labeled “Third-party app passwords” in Yahoo’s settings

6. My agent sees old emails but nothing new

Section titled “6. My agent sees old emails but nothing new”

Usually a sync state issue. Fix:

  • Disconnect and reconnect — nuclear but effective. Your agent re-initializes the IMAP state.
  • Check if your email provider is throttling us. If you have a huge inbox (50,000+ emails), the initial sync can take hours.

7. “The agent sent an email and it didn’t arrive”

Section titled “7. “The agent sent an email and it didn’t arrive””

Check your Sent folder in your actual email client. If it’s in Sent, it was delivered by your SMTP server but the recipient’s provider may have:

  • Spam-filtered it — ask them to check their spam folder
  • Rejected it — check the Sent folder; if the original shows a delivery failure, there’ll be a bounce notification
  • Quarantined it — corporate filters (Mimecast, Proofpoint) sometimes hold unexpected messages

8. Nuclear options

Section titled “8. Nuclear options”

If nothing above works:

  1. Go to Settings → Integrations → Email, find the broken inbox, and click Disconnect
  2. Wait 60 seconds
  3. Revoke the app password on your email provider’s security settings
  4. Generate a completely new app password
  5. Click Add email account and reconnect from scratch

This clears out any stale connection state on our side.