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"Whoops! We can't send the email." Error Message
"Whoops! We can't send the email." Error Message

What to do if you see this error message from Microsoft when sending an email in LeadSimple

Matt avatar
Written by Matt
Updated over a week ago

If you use Microsoft, you might encounter this error message when you try to send an email from LeadSimple at some point in time: "Whoops! We can't send the email. To fix the issue, update permission settings of your email provider".

This happens when you are trying to send an email using an alias as your "from" address. You might do this if you want to send emails from LeadSimple using your personal email address (e.g. but want it to look like it's coming from your primary support address (e.g.

NOTE: This set up πŸ‘† does not always work with LeadSimple; we strongly recommend creating a dedicated Microsoft user account for each email address you want to send from in LeadSimple and connecting that email account directly to LeadSimple.

However, you can fix this error by updating your permissions in your Microsoft Exchange admin center to allow your email account (e.g. to "send as" or "send on behalf of" a different email address (e.g.

These instructions were taken from this article.

  • Login to the Microsoft 365 Admin Center as a Global Administrator or an Exchange Administrator (Custom Role):

  • Navigate to the Exchange Admin Center

  • Under Mailboxes > Recipients, locate the User or Group you want to impersonate when sending emails from this Microsoft account (e.g.

  • Select the Edit icon

  • Under Group Delegation, add the account running the workflow (e.g. to the appropriate role

    • Send As: Recipient perceives that the email is delivered from the impersonated user or group.

    • Send on Behalf: Recipient perceives that the email is delivered on behalf of the impersonated user or group.

Authorize send as User or Group Delegation Exchange

Note: Please be patient for these changes to take effect. It could take up to 30 minutes for the user or group delegation to take full effect. Retest workflow after sufficient time has passed.

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