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Freshdesk allows you to connect your existing mailbox, such as Gmail, Microsoft 365, or another custom provider, to send and receive support emails. This article provides troubleshooting steps for common error scenarios and error messages that you may encounter while setting up and configuring custom email servers.


Prerequisites:

Ensure you have the following permissions:

  • Admin or agent access in Freshdesk.
  • Admin access to your custom email servers, such as Gmail or Microsoft.

Troubleshoot email errors

Custom email server errors in Freshdesk may fall into one of three categories:

  • Incorrect configuration (server name, port, or credentials)
  • Authentication issues (expired OAuth tokens or certificates)
  • Provider-side restrictions (IP whitelisting or sending limits)

The following table provides details on the different errors and the corresponding troubleshooting steps:

Error MessageReason for errorHow to resolve this?
Error while verifying the mailbox imap details. Please verify server name, port and credentials.

This occurs due to the following reasons:

  • Incorrect configuration, such as an invalid port number or wrong credentials
  • Invalid TLS certificate
  • Mailbox IP restrictions

  1. For Gmail or Microsoft Office 365 users:
    Ensure that IMAP is enabled in your Gmail or Microsoft Office 365 settings. For instructions, see Enable IMAP and SMTP settings.

  2. For other Custom Servers users:
    Verify the server name, port, and credentials for your custom email server. Ensure that you have entered the correct information on Freshdesk’s Email Settings page.

  3. Verify your TLS certificate

  4. Check email IP Whitelisting
    If the issue still persists, verify if the required Email IPs are whitelisted in your network or email server settings. This ensures that Freshdesk can securely connect to your email server.

Error refreshing access token.

This indicates that your OAuth token may have expired.Reauthenticate your access token on your account (Gmail or Microsoft 365) again.


To reauthenticate:

  1. Go to Admin Settings > Email > Custom Email Server.

  2. Click on the Sign-in button on the Email Configuration page.

    You will be redirected to your OAuth provider’s login page (Gmail or Microsoft 365).

  3. After successful login, a new access token will be automatically generated.
Specified IMAP mail server is not supported. Please use a different one.

This indicates that your client-side IMAP is disabled.

Ensure that the IDLE feature is enabled in the IMAP server settings of your accounts.  


To enable the IDLE feature in Microsoft 365, see Enable IDLE in Microsoft 365.


For other email accounts, check with your respective Email service providers.

Could not connect to the IMAP server. Please verify server name, port and credential.

This occurs due to any incorrect configuration.

For example, an invalid port number or mailbox IP restriction.

  1. For Gmail or Microsoft Office 365 users:
    Ensure that IMAP is enabled in your Gmail or Microsoft Office 365 settings. For instructions, see Enable IMAP and SMTP settings.

  2. For other Custom Servers users:
    Verify the server name, port, and credentials for your custom email server. Ensure that you have entered the correct information on Freshdesk’s Email Settings page.

  3. Check email IP Whitelisting
    If the issue still persists, verify if the required email IPs are whitelisted in your network or email server settings.

    This ensures that Freshdesk can securely connect to your email server. 
Error while authenticating the SMTP server. Please verify server name, port, and credentials

or

Error while authenticating the SMTP server. Please verify server

This occurs due to:

  • Incorrect configuration, such as invalid port number, and wrong credentials
  • Invalid TLS certificate
  • Mailbox IP restrictions


For Gmail or Microsoft Office 365 users:
  1. Ensure that SMTP is enabled in your Gmail or Microsoft Office 365 settings. For instructions, see Enable IMAP and SMTP settings.
  2. When setting up emails using Gmail, ensure to allow and grant read/write access permissions.


For other Custom Servers users:
Verify the server name, port, and credentials for your custom email server. Ensure that you have entered the correct information on Freshdesk’s Email Settings page.

You can also:
  1. Verify your TLS certificate

  2. Check email IP whitelisting
    If the issue still persists, verify if the required Email IPs are whitelisted in your network or email server settings. This ensures that Freshdesk can securely connect to your email server.
Error: Email sending limit exceededThis occurs to prevent the delivery of unsolicited bulk messages and ensure fair usage of our resources.Monitor your email sending volume to stay within the daily limit.

For Office 365 users:

Users and applications are currently restricted to sending 10,000 emails per day for Office 365. Additionally, a new daily External Recipient Rate (ERR) limit of 2,000 recipients for Outlook will be introduced in 2025. 


For Gmail users: 

If the daily sending limit is exceeded, the mailbox may be disconnected. For more information on Gmail sending limits, see Gmail Sending Limits.

Could not connect to the smtp server. Please verify server name, port and credentials.

This indicates that the TLS certificate expired or an unsupported TLS version is used on the client side. 

Update the TLS certificate of the email domain in your domain service provider.

Timed out while authenticating the SMTP server.

This occurs due to an invalid auth, port number or IP restriction.

For Gmail or Microsoft Office 365 users:

Ensure that IMAP is enabled in your Gmail or Microsoft Office 365 settings. For instructions, see Enable IMAP and SMTP settings.



For other Custom Servers users:

Verify the server name, port, and credentials for your custom email server. Ensure that you have entered the correct information in Freshdesk’s Email Settings page.

We're sorry, something went wrong. Please try again later.

Please contact us at support@freshdesk.com with the HAR logs. To know how to generate HAR files on different browsers, check Generate HTTP Archive (HAR) files.

Freshdesk is unable to send emails for custom mailbox; Please reauthorize.
You may receive an email notification with this error when there is a timeout error and Freshdesk tries to connect with the SMTP server of your mailbox. 
Reauthorize your custom mailbox. For instructions, see  Reauthorize Mailbox.
Something went wrong. We are unable to connect to your custom mailbox. View details.

This occurs when Freshdesk tries to connect to your mailbox and if the connection is not passed successfully.

Reauthorize your custom mailbox. For instructions, see Reauthorize Mailbox.

If the issue still persists, you can try the following alternate troubleshooting steps:
  1. Go to Admin > Channels > Email.
  2. Temporarily, assign a different support email or create and assign a dummy email as the primary support email using the STAR icon. The original support email that requires reauthorization will now become the secondary email.
  3. Reauthorize the secondary email (support@domain.com).
  4. Once this is done, click on the star icon again to revert the previously designated support email to the primary status.
Since you have connected Freshworks mail server, your email alias cannot be in public domainThis happens when you choose the Freshworks mail server to set up emails but have added an email address on a public domain like Gmail or Microsoft Office.

This is because 

Freshdesk cannot sign emails on behalf of public email domains.


Due to DMARC enforcement by public domains, this can affect email delivery may be affected, causing your emails to be dropped or sent to spam.

If you want to use your existing emails in the public domain, choose the appropriate server type (Gmail, Microsoft Office 365, or Custom server).
Your authentication has expired. Please sign in againYour email authentication has expired.Reauthenticate your email and try again.
This email ID is already configured on this account. Add an email alias or use a different email ID. This occurs when you add an existing email ID.Try adding a different email ID or use an email alias.


Enable IMAP and SMTP settings

To resolve IMAP- or SMTP-related errors, ensure both protocols are enabled on your mailbox.


Enable IDLE in Microsoft 365

If you use Microsoft Office 365 as a custom mail server, check if SMTP is enabled on your mailbox.

  1. Open the Microsoft 365 admin center using Office 365 credentials and go to Users > Active users.
  2. Select the user with the custom mailbox configuration, and in the pop-up that appears, click the Mail tab.
  3. In the Email Apps section, click Manage Email Apps.
  4. In the Manage email apps pane, ensure “IMAP” and “Authenticated SMTP” options are enabled.
  5. Click Save.
Note: Most Microsoft Office 365 tenants have SMTP authentication disabled by default. You can enable it if required. It takes about 30 minutes for the permissions to take effect. For more details, see Enable or disable authenticated client SMTP.


Enable IMAP and SMTP in Gmail

To check your IMAP and SMTP settings in Gmail, go to your Gmail account > Settings and confirm both protocols are enabled.

Generate HTTP Archive (HAR) files

If an error persists after you've tried the resolutions in this article, send the HAR logs to support@freshdesk.com. A HA


Generate HAR file in Google Chrome

To generate a HAR file in Chrome, follow these steps:

  1. Close all incognito windows in Google Chrome.
  2. Open a new incognito window in Google Chrome.
  3. Go to View > Developer > Developer Tools.
  4. In the Developer Tools pane, choose the Network tab.
  5. Enable the Preserve Log checkbox to record all interactions.
  6. Visit the page and complete the steps that trigger the issue.
  7. Choose the Network tab.
  8. Click the down arrow to export the HAR file.
  9. Save the HAR file.

Generate HAR file Safari

To generate a HAR file in Safari, follow these steps:

  1. Go to Safari > Preferences > Advanced, and ensure that Show Develop menu in menu bar is selected.
  2. Go to File > Open New Private Window.
  3. In the Developer menu, select Show Web Inspector, and go to the Network tab.
  4. Click Filter and select Preserve Log.
  5. Go to the page where the issue occurs.
  6. Select Develop > Show Web Inspector. The Web Inspector window appears.
  7. Complete the steps on the page that trigger the issue.
  8. Select the Network tab.
  9. Click Export in the top-right corner and save the HAR file.

Generate HAR file in Firefox

To generate a HAR file in Firefox, follow these steps:

  1. Close all private windows in Firefox.
  2. Open a new private window in Firefox.
  3. Go to Tools > Developer > Network (Ctrl + Shift + E).
  4. Click Network and select Persist Logs.
  5. Visit the page and complete the steps that trigger the issue.
  6. On the Network tab, right-click and select Save All As HAR.
  7. Save the HAR file.

Generate HAR file in Microsoft Edge

To generate a HAR file in Microsoft Edge, follow these steps:

  1. Close all InPrivate windows in Microsoft Edge.
  2. Open a new InPrivate window (Ctrl + Shift + N).
  3. Go to Settings and more and choose More Tools > Developer Tools.
  4. Start a profiling session on the Network tab of the Developer Tools toolbar.
  5. Go to the page and complete the steps that trigger the issue.
  6. Select Export as HAR (Ctrl + S) and save the HAR file.