This feature requires a Microsoft 365 administrator account. Select Run Tests: Outlook User Connectivity to download and run the diagnostic. The diagnostics perform automated checks to detect issues and provide possible solutions to fix them. So, if your ISP's SMTP server does not allow port 587, you won't be able to send e-mails until you change the SMTP port to 25. Run a Microsoft 365 Diagnostic: There are Microsoft diagnostics that you can run to troubleshoot connectivity issues. I've noticed that Microsoft has changed the default SMTP port in Outlook 2007 from 25 to 587. It can't only be me who is getting this error? Is it a known 'bug', or is there some logical explanation? I have searched for an answer on Google using the error code, but no luck so far in resolving the issue. I have always had this problem, both in the UK and now here in Thailand where I work. I don't see this as anything other than an Outlook problem (rather than a server problem) because if I close Outlook and start it up again (and I sometimes need to open the message in the Outbox and click 'Send' again), the message is then always sent. If you continue to receive this message, contact your server administrator or Internet service provider (ISP).' Task - Sending' reported error (0x80042109) : 'Outlook cannot connect to your outgoing (SMTP) e-mail server. Half the time I try to send emails I have written (Outlook 2007) I get the following error message:
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