TWO POSSIBLE FIXES USING GOOGLE AUTHENTICATION SERVICES

Hey, Nisa51,

I just had the same outgoing server SMTP errors happen on my Samsung Galaxy 
S4 using K9 Mail (imap access) which I use solely for accessing e-mail from 
an alternative/secondary google account (my main google account synced to 
the phone uses the phone's native gmail app and functioned fully without 
errors). 

ERROR HISTORY/BACKGROUND
K9 Mail had always worked fine on my Samsung Galaxy S4 running 4.4.2 until 
recenty when I noticed failure notices after attempting to create and send 
an e-mail (error "Cannot connect to server. Negative SMTP Reply 534 ..."). 
While any incoming mail continued to arrive as always, any attempts to 
compose/send new e-mail messages from my phone using K9 ended in a 
connection error and became stuck in the Outbox. Full disclosure, I mostly 
compose and send e-mails for this secondary google account using my laptop 
and the chrome browser; I hardly ever use K9 on the phone for anything but 
reading incoming mail, so I suspect the error may have been in place for a 
while.

I have enabled 2-Step Verification for both my main and secondary google 
accounts which is where I should have started investigating rather than try 
every fix suggested across various forums (from changing port number to 
cycling through the four authentication types). After coming across a 
possible solution posted in repsonse to more generic gmail smtp failures, I 
went into my google account's security settings to double check whether I'd 
given K9 access (from google:  settings > security > select "settings" to 
the right of 2-Step Verification line in the password section). Strangely, 
I saw that I'd already created an app-specific password for K9 Mail and 
that it had been used successfully a few minutes earlier (spoiler alert: it 
was for incoming server access only). 

Depending on whether you have 2-Step Verification enabled or not, here 
follows two possible fixes (the first one fixed my smtp failures 
immediately):


*1.) ENABLED 2-Step Verification - Create Two Separate App-Specifc 
Passwords for BOTH the Incoming and the Outgoing Server*
[see attached image 01]

When I'd originally granted K9 access to google, I'd only bothered entering 
the app-specific password into the incoming server section. So, if you have 
2-Step Verification enabled on your google account and are having trouble 
sending mail through imap with applications like K9 Mail, check to make 
sure you have granted K9 Mail access for both INCOMING and OUTGOING 
authentication with an app-specific password created for each function. 
Create the second password and replace your regular account password with 
the new one in the Outgoing Server Settings within the K9 Mail app (mine 
was composed of four sets of four numbers with a space between each set. I 
entered the spaces as characters for a total of 19 character spaces in the 
app-specific password). Almost instantly after creating the second 
app-specific password and entering it, my outgoing e-mail started to 
function as normal. So, the only change you'd need to make in K9 is the 
outgoing server password.

*2.) INACTIVE 2-Step Verification (e.g. You Don't Use It) - Google 
DisplayUnlockCaptcha Service to Allow Individual App Acccess*

[see attached image 02]

If *you have not enabled 2-Step Verification*, here is a solution (with 
some rewording/clarification done by me) found posted on stackoverflow.com 
<http://stackoverflow.com/questions/17462380/server-send-emails-using-gmail-smtp-gets-alerts>
 
which still identified the google authentication process as the culprit for 
outgoing mail SMTP errors:

Apparently, google has to specifically grant/allow some applications access 
to your google account even if you've supplied the correct credentials 
(usually for a new application). K9 Mail and similar apps that access your 
google account may need to go through this secondary level of permissions. 
Even if you've been using the app succesfsfully for some time, it might be 
that the app was recently updated and it's being treated as "new," or you 
may have made some recent global changes to the phone itself (from OTA 
updates to rooting).  In order to do grant the offending app access, google 
set up an authentication procedure. After logging in to google in a 
computer browser, navigate to 
https://accounts.google.com/DisplayUnlockCaptcha. Click *Continue* when 
you're ready and, within the next 10 minute time limit, try again to 
compose and send an e-mail within K9 Mail (delete and do not attempt to 
"re-send" any mail that are stuck in the outbox or which failed earlier - 
instead, create a completely new outgoing e-mail message). Over the next 10 
minutes, google will be sniffing for any apps attempting to access your 
account that it doesn't recognize. As long as the account information used 
by K9 or other apps is accurate (e.g. your gmail address, password, et al) 
it should then grant it permission to access your google account as well as 
remember the new application/service (until the next time you change that 
google account's password).

Hope one of these two solutions helps!

~Southern Dude 

On Sunday, September 21, 2014 11:00:53 AM UTC-4, Nisa51 wrote:
>
> I have a Galaxy S3 and have used K9 for 3 of my accounts and now 2 fail 
> completely to send I can receive with no problem but cannot send. I have 
> not altered any settings for the outgoing servers and have checked the 
> settings are they are fine.
>
> The other is a gmail account and that works fine sending and receiving.
>
> Incoming server
> Pop3 and imap port 110
>
> Outgoing server
> smtp 
> Security None
> Port 587
> Require Sign In
> authentication - Automatic
>
> Now this does not work I get a message - Cannot connect to server. (No 
> valid authentication mechanism found)
>
> If I untick the Require Sign In box it works!!
>
>
>

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