'Allow insecure authentication' selection not saving in mac mail

tried 25 and 587 tried smtp.livemail.co.uk and smtp.mydomain. works fine on iMac with maverick. works fine on iPad using wifi on same network.

since i wrote the log i have deleted all the smtp entries and re-added them one by one. info@domain1.co.uk worked (starter plus) bookings@domain1.co.uk worked (starter plus) but when i add user1@domain2.co.uk (starter plus) it won't work. same settings.

next thing I'm going to do is delete them again and then delete the keychain entires and then re-add them just in case I'm getting a password coming from somewhere as i changed my password on Saturday when I had the problem first time around on the iMac.

I'm off to bed. can't spend anymore time on this tonight.😕

In your earlier post you mentioned deselecting the 'Automatically detect and maintain account settings' on the SMTP Advanced tab. I checked my Fasthosts account and found the checkbox selected; on deselecting it I found that I couldn't send a message, but reselecting it again enabled the sending of the message immediately! It would appear that you need to desert the checkbox for the IMAP settings and select it for the SMTP settings!

very interesting. i just deleted the smtp settings from mail, closed mail, deleted all my keychains for smtp.livemail.co.uk for one of the email addresses, dopened mail and then added the smtp entry with smtp.livemail.co.uk port 25 AND accidentally forgot to uncheck the automatically detect box and IT WORKED. So far i have four email addresses working and three more to do. looks like this could be a problem with keychain entries not getting deleted and some yosemite bug.

must go to bed though! imleaving the other three until tomorrow and see if these are still active in the morning.

thanks once again for your efforts to help🙂

I seem to have the opposite problem but I'm not sure what's going on.

I run a personal mail server and it's throwing this error for me. However in my case the "Allow insecure authentication" box is already checked so there's nothing I should need to do but it keeps informing me that it can't use my personal mail server to send the message because it can't transmit the password securely. Is it just ignoring the checkbox or something? Is this security layer something new for Yosemite?

Not sure this will help but after much persistence I have it working.

The steps to rectify the situation are as follows;

1. I have unchecked automatically detect and maintain account settings on the account advanced tab/

2. I have checked "allow insecure authentication" on the account advanced tab.

3. I have checked "automatically detect and maintain account settings" on the advanced tab of the SMTP definition.

This had limited success and suspected the problem was associated with old keychain entries.

so I followed up with this procedure.

4a Deleted ALL SMTP definitions.

4b closed mail

4c. Went into the keychain and removed all references to smtp.livemail.co.uk

4d. Opened mail and add SMTP definitions manually. with settings.

Port 25

smtp.livemail.co.uk

Leave "automatically detect and maintain account settings" checked (SMTP only remember)

Password authentication

4e. Connect the relevant account to the newly added SMTP definition and all OK.

I know I have jumped on your post an probably frustrated by the email stream but it is the same issue and Jan C solution did not resolve the issue completely.

If you haven't got anything constructive to add then don't bother.😁

I think I acknowledged that my original solution wasn't the complete answer, didn't I? Although the Yosemite/Safari autocorrect in my last post chose to make 'deselect' into 'desert', which totally ruined the context of what I was trying to get across (and I didn't notice it at the time)!!

I think what has come out of this thread is that the solution I put forward worked as long as everything else was functioning correctly; by chance, the SMTP setting didn't get deselected because I hadn't realised it was there until you mentioned it! Other problems that others are experiencing, such as in Keychain seem somewhat arbitrary and more a product of the system rather than the Mail account settings. 😀

But I don't have the "Automatically detect and maintain settings" box checked and I do have the "Allow insecure authentication" box checked.

Does this have something to do with the mail server I'm connecting to?

Obviously, we can't be sure, as we don't know which server you mean! I suggest you ascertain what your mail servers (IMAP and SMTP) require and set up your account for that server accordingly. Check what happens and play with the various check boxes until you get the result you want. It's a little bit like flying a helicopter: you waggle the sticks around until the aircraft flies the way you want - and you remember where the sticks were went it did so, 'cos that's where to put them the next time!!! 😉

[Solved] - At least for me.

you need to find and edit the Account.plist which is in MailData directory in your Library folder.

mine is in /User/myaccount/Library/Mail/V2/MailData

Find the account that is having issues with SMTP and edit the settings (I used sudo vi Account.plist) as follows

Relaunch Mail and ... voilà ...

Maybe it is better to make a copy of Account.plist before editing ... ;-)

key>PortNumber</key>

<integer>587</integer>

<key>ShouldUseAuthentication</key>

<string>NO</string>

<key>UserAllowsInsecureAuthentication</key>

<true/>

Its great that you could manage it - I have the same Yosemite Upgrade on a new Macbook and same SMTP Problems with 4 Imap Accounts!

I have several questions to follow your resolution and do the same for me... can you be a bit clearer for the following unclear parts please...:

4a. where exactly?

4b clear

4c where? how?

4d manually, where exactly?

4e connect to smtp definition => means? how exactly?

Sorry for making you extra work - but you are saving my Yosemite from being deleted! 🙂 THANKS

Thanks Jan, this also worked for us. We're just wondering what the disadvantages of using "insecure authentication" are though. Do you know if this means it doesn't use SSL to connect? If this is he case, is there not a greater chance of the sender's emails being misidentified as spam by receiving servers that check their authenticity?