SOLVED Outlook 2016 sending issues

[RobynRene]

Hello- I can't get my Outlook 2016 (windows 10 on a dell pc) to send my emails. I am receiving without problems. error message just says cannot connect with my outgoing smtp server. have been on the phone with my service provider, my internet provider, microsoft support and Office 365 support with no resolution I've tried the sfc /scannow with no resolution. anyone have any other ideas? It's working on my iMac with the Mail app just fine

 

[Trouble]

Would you mind telling us, who you email service provider is?
Perhaps someone using the same provider may have a suggestion.
Usually these types of problems come down to configuring the details with respect to ports and encryption required by your provider which I assume you have on hand as you've contacted them for those details.

 

[RobynRene]

chicagowebs.com hosts my website and email

 

[Trouble]

I assume they have explained whether or not this box needs to be checked or unchecked?

As well as these setting....

 

[Tim Locke]

IN the setting screen for an account there is the option to test the settings. Outlook will go through a send receive sequence and give you an error on what is wrong. From your post I guess you have probably done that several times!
IIRC Outlook prefers IMAC. Is your connection IMAP or POP to the provider. If it is IMAP on the receiving end can you change that to POP if your provider supports it? Can you see what the numbers for ports and encryption are on the MAC ?