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]
>
> 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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