Hello @Syed Fazal Hassan ,
Based on your error message, I would like to confirm with you whether you have made any changes to the server recently? It is recommended that you first test the connection to the remote SMTP server using telnet on port 25 to ensure that port 25 is not blocked or filtered by the firewall or ISP, as it may be that your ISP blocks the port. Here are some similar cases for your reference: https://techcommunity.microsoft.com/t5/exchange/444-4-4-1-error/m-p/3278252 https://thesysadminchannel.com/solved-exchange-failed-to-connect-winsock-error-code-10060-win32-error-code-10060/(Please Note: Since the web site is not hosted by Microsoft, the link may change without notice. Microsoft does not guarantee the accuracy of this information.)
In addition, for further troubleshooting, could you provide the output of using ipconfig /all on the Exchange Server?
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