Why Clients Are Not Receiving Your Emails (T183, Messages, Authorization, Document Requests) | CloudTax EFILE

If your clients are not receiving emails from CloudTax EFILE, it is usually caused by an issue with your email connection settings.

This can prevent important communications from being delivered, including:

• T183 signature requests
• Secure messages
• Document requests
• Authorization requests
• Client invitations
​

When the email connection fails, our EFILE software cannot send these notifications to your clients.

You may notice one or more of the following:

• Clients report they never received a T183 signing request
• Clients cannot see document requests
• Authorization requests are not delivered
• Secure messages are not arriving
• Test invitations sent to yourself do not arrive
• A red Email Delivery Error appears in Settings

In most cases, this happens when the connected Gmail or Google Workspace account can no longer authenticate with CloudTax.

The most common cause is a Gmail authentication error.

For example, you may see an error similar to: 535-5.7.8 Username and Password not accepted

This means Google rejected the login credentials used by the email connection.

This can happen if:

• Your email password changed
• Google security settings blocked the connection
• Two factor authentication was enabled without using an app password
• The connection token expired

Follow these steps to reconnect your email account.

Go to Dashboard → Settings → Email

Check if you see an Email Delivery Error message.

Click Disconnect on the Gmail / Google Workspace connection.

Reconnect the email account and follow the authentication prompts.

Click Test Connection to confirm that email sending works.

Once a test email is successfully sent, the error message will automatically disappear.

After reconnecting your email, you can confirm everything works by:

• Sending yourself a test message
• Sending a document request
• Sending a T183 signature request

If the email arrives successfully, your connection is working properly again.

If clients are still not receiving emails after reconnecting:

If the issue continues, please contact CloudTax Support and include a screenshot of your Settings → Email page.

Our team will help you restore your email connection quickly so your clients can receive their requests and documents without interruption.