cannot send mails to gmail

Question

Mickey Shahak 0

Hi,

Mails that I send to Gmail address do not arrive the recipient.

Mickey Shahak 0 Reputation points

2025-11-23T12:22:38.2866667+00:00

The problem us new (last week) It worked before. No changes were made in my Outlook. Problem with several Gmail addresses,

1 answer

Mickey Shahak 0 Reputation points

2025-11-23T12:22:38.2866667+00:00

The problem us new (last week) It worked before. No changes were made in my Outlook. Problem with several Gmail addresses,

Answer 1

Hi, I'm John! I will help you with this.

To help narrow down the issue:

Are you using Outlook for personal or Outlook for business?
Do you get any error message or bounce-back email when sending to Gmail? If yes, could you share the exact error? That will tell us if Gmail is blocking it or if Outlook is having trouble sending.
Have you tried sending from Outlook web https://outlook.live.com/mail as well? Could you test and let me know how it goes.

Another test:

Were those emails containing any document files or attachments? If so, may I know if the issue happens with a specific file format (like PDF, DOCX, ZIP, etc.)? Sometimes Gmail filters can block certain attachments.

Click "Add comment" to let me know.

Regards,

John J.D.