The operation timed out waiting for a response from the sending (SMTP) server. If you continue to receive this message, contact your server administrator or Internet service provider (ISP).

I was getting below error while setting up an email account in Outlook using POP setup with SSL -
 
The operation timed out waiting for a response from the sending (SMTP) server. If you continue to receive this message, contact your server administrator or Internet service provider (ISP).

Note - Make sure, you're using correct incoming and outgoing mail server while configuring an email account.

Solution :-

On Outgoing Mail Servers tab, select the 'My server requires authentication box', use the default option of 'Use same settings as my incoming server' .
 
Click the Advanced tab, and under Server Port Numbers , enter the following information:

· In the Incoming mail (POP3) box, type 995.
· In the Outgoing mail (SMTP) box, type 465.
· Under both Outgoing mail (SMTP) and Incoming mail (POP3), select the ‘requires secure connection (SSL) ’ check box.
 
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