That was it! As soon as I switched to STARTTLS (I was using SSL/TLS)  the 
outbound connection worked. 

On Sunday, August 30, 2015 at 10:16:56 AM UTC-5, Richard wrote:
>
>
> Normally you use the STARTTLS, not the SSL/TLS, "Security" setting 
> used in the "answers.ms" posting with port 587. [You would almost 
> never use SSL/TLS on port 25 - which is very frequently blocked 
> anyways.] The SSL/TLS option assumes that the server is doing 
> encryption from the start while STARTTLS negotiates things. I do 
> believe that K-9's STARTTLS's settings were changed last fall to 
> require encryption (rather than making it option) on the server 
> side, but since the documentation indicates TLS that shouldn't be an 
> issue.   
>
> The actual protocol negotiation may fail if, for instance, the 
> server side only offers a lower level than the client is willing to 
> accept. 
>
> I can't tell whether you used STARTTLS or SSL/TLS initially, but if 
> the former, a protocol mismatch may be the issue. 
>
> [ultimately, your bigger problems are that you are using pop (and 
> hotmail).] 
>
>
> > Date: Sunday, August 30, 2015 07:48:19 -0700 
> > From: [email protected] <javascript:> 
> > 
> > I continue  my search and also found this thread on another site 
> > from some  time back: 
> > 
> > http://answers.microsoft.com/en-us/outlook_com/forum/oemail-oapps/ 
> > imap-smtp-error-setting-up-in-android/a5dc7b79-d1f9-4887-8a1d-a75c 
> > bc79c878?auth=1 
> > 
> > 
> > 
> > On Saturday, August 29, 2015 at 10:29:28 AM UTC-5, 
> > [email protected] wrote: 
> > 
> >> I'm trying to set up my Hotmail accounts with the following on an 
> >> Android  Galaxy Note Edge: 
> >> 
> >> Incoming (POP3) Server 
> >> 
> >>    - 
> >>     
> >>    Server address: pop-mail.outlook.com 
> >>    - 
> >>     
> >>    Port: 995 
> >>    - 
> >>     
> >>    Encrypted Connection: SSL 
> >>     
> >> - 
> >> 
> >> Outgoing (SMTP) Server 
> >> 
> >>    - 
> >>     
> >>    Server address: smtp-mail.outlook.com 
> >>    - 
> >>     
> >>    Port: 25 (or 587 if 25 is blocked) 
> >>    - 
> >>     
> >>    Authentication: Yes 
> >>    - 
> >>     
> >>    Encrypted Connection: TLS 
> >>     
> >> - 
> >> 
> >> User name: my email address 
> >> - 
> >> 
> >> Password: my email password 
> >> 
> >> I know for sure that the email/password combo is correct, but I 
> >> am getting  the error that Setup couldn't finish as 
> >> authentication failed on POP and  handshake failed on SMTP. 
> >> 
> >> Anyone else seen this and have any ideas? 
>
>
>

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