I also had to set up an "App Password" in GMail and use that generated 
password in the MLO Tools/Options/E-mail Account dialog, in the password 
field.
I used the instructions here from Google, and they worked fine for me.  
https://support.google.com/accounts/answer/185833?hl=en 
These instructions from Lifewire give more details and screen shots:
https://www.lifewire.com/get-a-password-to-access-gmail-by-pop-imap-2-1171882

For the SMTP Server settings, I used smtp.gmail.com and port 587, with the 
"Use SSL" box checked.  Also port 465 works as well.  I think using port 
587 causes the newer TLS to be used while 465 uses the older, less secure 
SSL.

On Tuesday, September 8, 2020 at 8:35:07 PM UTC-7 [email protected] wrote:

> Just to attach specific file names here for users performing searches in 
> the future, this link is where you get the libeay32.dll and ssleay32.dll 
> files MLO's warning dialog tells you to find on the site when you try to 
> set up the desktop app to send email from your email client.
>
> On Wednesday, September 25, 2019 at 11:37:32 AM UTC-7 Alyona (MLO Support) 
> wrote:
>
>> You need to download DLL for connection through https, follow this link: 
>> https://www.mylifeorganized.net/downloads/files/openssl-dlls.zip . Unzip 
>> it and place to the folder where mlo.exe is stored.
>>
>>
>> On Friday, September 6, 2019 at 9:01:31 AM UTC+3, Ron Thompson wrote:
>>>
>>> I'm trying to set up email in MLO 5 for Windows (using Win10), but when 
>>> I try to test it, I get the captioned error message. How do I fix this?
>>>
>>

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