What's happening?
Microsoft (which operates Outlook.com, Hotmail.com, Live.com, and many business email addresses) uses automated spam filtering that can temporarily delay or block emails from legitimate senders.
This affects thousands of businesses that send email at scale — not just CheckCherry.
When this happens, a small percentage of emails to Microsoft-hosted addresses may be delayed or not delivered on the first attempt. Emails to Gmail, Yahoo, and other providers are not affected.
How do I know if an email was affected?
If a recipient using an Outlook, Hotmail, or Live email address reports they didn't receive an expected email (such as a proposal, booking confirmation, or payment receipt), this may be the cause. You can check the status of sent emails in your Activity Log.
What is CheckCherry doing about it?
We actively monitor our email deliverability and maintain excellent sender reputation scores with all major email providers, including Microsoft. Our complaint rate is below 0.1% and we follow all email authentication best practices (SPF, DKIM, DMARC). We are in direct contact with both Microsoft and our email infrastructure provider to resolve temporary blocks as quickly as possible.
What can I do in the meantime?
Resend the email. Temporary blocks usually clear within minutes. Going to the event or lead and resending the message will typically go through on the second attempt.
Ask your client to check their spam/junk folder. Occasionally Microsoft will deliver the email but route it to junk.
Use an alternative contact method. If an email is time-sensitive, consider following up via SMS through CheckCherry or calling the client directly.
Add to safe senders. Ask clients who regularly miss emails to add your sending address to their Outlook safe senders list.
Is my data or account affected?
No. Your account, data, and all other functionality are completely unaffected. This is strictly a temporary email delivery issue with Microsoft's spam filtering infrastructure.