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Why Can't I Send Emails? Common Email Errors

Troubleshoot why you are unable to send emails.

Aimee avatar
Written by Aimee
Updated this week

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 support@leadsimple.com 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 support@leadsimple.com.

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 support@leadsimple.com and we will upgrade your account with our 3rd party email connection provider Nylas to ensure your connection is up to date.

"Limit Exceed for emails" or "Rate Limited Exceed! You can't send that many emails"

If you see this error when trying to send an email it could be due to an over due balance on your LeadSimple account as this does impact your rate limit. Please check to ensure that your billing is paid and up to date.

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

If you notice that your emails were sent from a sendmessenger.com 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 sendmessenger.com 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.

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

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. bob@example.com) but want it to look like it's coming from your primary support address (e.g. help@example.com).

NOTE: This set up 👆 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. bob@example.com) to "send as" or "send on behalf of" a different email address (e.g. help@example.com).

These instructions were taken from this article.

  • Login to the Microsoft 365 Admin Center as a Global Administrator or an Exchange Administrator (Custom Role): https://portal.office.com/adminportal

  • 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. help@example.com)

  • Select the Edit icon

  • Under Group Delegation, add the account running the workflow (e.g. bob@example.com) 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.

"Error Quota Exceeded" error when sending emails

If you use Microsoft as your email provider, you may run into this error code: "ErrorQuotaExceeded".

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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