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Why Can't I Send Emails?

Troubleshoot why you are unable to send emails.

Aimee avatar
Written by Aimee
Updated over a week ago

Having trouble sending emails? Review the errors below and click on them to see their fixes. If you don't see your error listed, check out this article and then reach out to and we'll investigate with you.

Emails appear to send but the recipient never receives them

This can happen with Microsoft/Outlook accounts when your email account has two different emails - one as your User Principal Name (essentially your username) and another as your Mail Nickname (your actual email address).

You will need to login using your User Principal Name address instead of your actual email address when connecting your email account to send emails through LeadSimple.

Reach out to Microsoft or your IT help desk if you need help identifying whether you have a separate User Principle Name and Mail Nickname.

"Error encountered when sending using Gmail API"

Sometimes when you try to send an email through LeadSimple, you may run into the error "Error encountered when sending using Gmail API".

This error is an issue caused by Gmail with connected gmail accounts. You may find that it is an intermittent problem - we are working with Gmail to implement a fix. If it persists, contact us at

Remember that you can always email leads inside your gmail inbox and those emails will be synced back to the lead in the system.

"PERMISSION_DENIED: Request had insufficient authentication scopes"

You might encounter this error when the first time you connected your email you didn’t give Lead Simple enough permissions. To fix this, all you need to do is reconnect your email and check all the boxes on the Gmail page when you connect your account.

"Access Denied: You need to reconnect your email account"

When you try to send an email through LeadSimple, you may sometimes encounter an error that says "Access Denied: You need to reconnect your email account".

This means that your email account has become disconnected from LeadSimple so the software can't send emails from that email address until you reconnect it.

Reconnect it following these steps.

"Required SMTP STARTTLS not Supported"

This error can appear on emails hosted by RackSpace.

The first step to try is to delete and reconnect your email.

If that doesn't work, open a support ticket with Rackspace and let them know LeadSimple is receiving this error from them when sending an email. They typically resolve these errors in 1-2 days.

"Account cancelled or trial expired"

If you see this error when trying to send an email, reach out and we will upgrade your account with our 3rd party email connection provider Nylas to ensure your connection is up to date.

My emails are going out from a email rather than my email account

If you notice that your emails were sent from a email account rather than your email account, you will need to do one of three things:

  • Reconnect your email account to LeadSimple (if it is disconnected)

  • Connect your individual work email as a direct email account in LeadSimple instead of a shared email account

  • Set one of your emails (shared or direct) as your default email account on your profile.

LeadSimple uses as a fallback email service when you do not have an email account connected or do not have a default email set on your profile.

How to Reconnect Your Email

First, go to your profile page by clicking your name in the top left.

Scroll down to Email Accounts and find your disconnected email account.

Next, click "Reconnect" next to the email account. You may be prompted to provide additional information so simply follow them when they appear.

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