Fixing Connected Account Problems

A connected account not syncing, or asking you to reconnect? Common fixes for password, app-password, and server errors when connecting Gmail, Yahoo, or IMAP.

Article details

Type, difficulty, plans, and last updated info.

Type
Guide
Difficulty
Beginner
Plans
Nano · Starter · Pro · Agency
Last updated
Sep 9, 2026

Connected accounts usually work without attention. If one stops syncing or asks you to reconnect, use the message you see to choose the right fix.

Reconnect needed or an amber dot

An amber dot or Reconnect needed means the saved sign-in details need attention. A changed provider password, revoked app password, or Microsoft access token that needs new consent can cause this. Open Settings → Connected accounts, choose the account, update the requested sign-in details, and test it again. TrekMail tests the connection before saving the update.

Authentication failed

Check the sign-in method required by the provider. Gmail, Yahoo, AOL, and iCloud use an app password for this connection, not the normal login password. Copy the whole value and make sure the provider still offers app passwords for the account. Replace any browser-filled username with the exact address of the mailbox you are connecting.

Sending works but receiving does not, or the reverse

Reading uses the IMAP server and sending uses the SMTP server. Compare the host name, port, encryption, username, and app-password requirement for the failing side with the provider's mail-client setup page. The connection starts from TrekMail's servers, not your phone or laptop, so changing local Wi-Fi or mobile data will not alter the result.

Cannot reach the server or a timeout

Confirm that the server name is correct and that the provider offers IMAP and SMTP. Some basic plans turn IMAP off by default, so enable it in the provider's settings if necessary. A server your organization runs must be reachable from the public internet; a private office-only address cannot be connected.

Certificate error

TrekMail requires a current public certificate that matches the server's host name. A self-signed, expired, or mismatched certificate cannot be accepted. Ask the provider or server administrator to renew the certificate and confirm the correct host name, then test again. Do not use an IP address to bypass a certificate error.

Outlook.com or Microsoft 365 needs reconnecting

Microsoft accounts use secure Microsoft sign-in, not a password, and their access is normally refreshed automatically. If an Outlook, Hotmail, or Microsoft 365 account needs reconnecting, you may have changed the Microsoft password, revoked access, or need to renew consent. Open Settings → Connected accounts, choose the account, then select Reconnect with Microsoft. The account keeps its settings. Microsoft sign-in is not offered on a branded White Label host. See Add Your Outlook.com Account to TrekMail for the full flow.

Microsoft 365 asks for admin approval

Personal Outlook.com and Hotmail accounts connect on their own. Work or school Microsoft 365 mailboxes are controlled by the organization. If Microsoft says an administrator must approve access, or IMAP is off for the mailbox, ask the IT administrator to allow it and try again.

Still stuck?

Open a support ticket and include the provider and the exact message you see. Do not include a password or app password.

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