This is got irritating now I had an update today from k9 and the email 
stopped working and there is no setting for the PLAIN its gone.
Think I will scrap K9 and look for something else.
On Thursday, 25 September 2014 16:00:41 UTC+1, Nisa51 wrote:
>
> Hi Southern
> My Google accounts via K9 are fine I have no problems with that at all. 
> But I have fixed the one I was having problems with which was an old 
> Tiscale email address. The setting was using Port 587 and then for 
> Authentication use PLAIN. It was set at Automatic before I just altered it 
> to PLAIn and it's working brilliantly.
>
> On Thursday, 25 September 2014 15:52:49 UTC+1, Southern Dude wrote:
>>
>> 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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