'Allow insecure authentication' selection not saving in mac mail

The 'Allow insecure authentication' check box is on the Advanced tab of the account that can't use TLS/SSL; it must be selected. Above the checkbox is the check box for 'Automatically detect and maintain account settings', which must be DESELECTED to ensure that Apple Mail doesn't reset the authentication check box as soon as your back is turned!!!

I also have unsecure IMAP accounts (I have four email addresses) and when I upgraded I saw the Allow insecure authentication so checked it and then found it reverted so I checked it again and also unchecked the 'Automatically detect and maintain account settings'.

I then had a problem where the SMTP server keep dropping its connection and the only way to get it back was to delete the SMTP definition and recreate it.

After spending several hours trying to get it working and talking to the email hosting support (FASTHOSTS in the UK) I gave up and restored to Maverick.

Anybody out there using Fasthosts, multiple email accounts and has this working? Or even not using FASTHOSTS and has this working.😕

Anybody upgraded with multiple email addresses (same domain) and using SSL got this working?

Not sure if I should talk to Apple support but that costs £35 and I needed to move on so restore was faster.

thanks in advance for any help out there 😀

Unfortunately it does not work for me.

I check Allow insecure authentication but this option is not saved (althought I'm asked to save it).

Have you unchecked 'Automatically detect and maintain account settings'?

I am a little confused by your post. This thread deals with email accounts that do NOT use SSL/TLS, but your last question "Anybody upgraded with multiple email addresses (same domain) and using SSL got this working?" would suggest that you shouldn't be using this solution.

As it happens, I have a domain on a Fasthosts shared server and I have several email addresses (I'm the administrator for the domain) accessed through Apple Mail; I no longer have any problem since using the settings specified in my earlier post. However, Fasthosts had problems over the weekend, so that might be the cause of your difficulty.

yes, I've done everything, either on IMAP setting or SMTP settings.

If I go back to preferences it is still unchecked

the fact is that now no changes in preferences are saved for that account ...

... and of course same settings on Mozilla Thunderbird work perfectly ....

I'll stay on MT until Apple will fix this bug

I was only asking about SSL to see if anyone had email working with SSL but not relevant to my problem.

As I stand now I have restored back to Maverick so will need to upgrade again when time allows. I thank you for your comments as it does sound like the problem was related to fasthosts problems this weekend but my iPhone was working OK and support did not suggest that my problem was relating to their ongoing problems. At least you have it working which suggests that mine config should work.🙂 Are you concerned about using mail without SSL from a security aspect ?

Much appreciate your answer 🙂

So, in answer to the first part, I run my own postfix/dovecot/etc/etc server on a Mac Mini running Mavericks (server). I have no problem with my Apple Mail accounts that use TLS/SSL with my server, as the Apple Mail default is to use secure comms. The problems arose when the Apple Mail Preferences tried to use that default even though the 'Allow insecure authentication' had been checked!! My solution above resolved that particular problem.

To your question about using mail without SSL, yes, I am concerned to an extent, but there is little I can do about that given the lack of secure facilities offered by Fasthosts (without considerable extra cost!!).

Jan

You are a God send!

I have been struggling with this since last Thursday. Your advice like all the best solutions is simple but effective

Thank you for giving me my life back!

Mike

My own set up mirrors yours. I have a Fast Host account. I have spoken to them a great deal over the last 5-6 days and they have been fast (no pun intended) to blame Apple

I have implemented Jan's fix and, fingers crossed, it appears to have resolved my issues🙂

thanks for the feedback mikefromeastbourne and janC but I'm still not working!

i have just installed yosemite on a macbook air and it all seemed to be working ok but then the smtp connection goes offline.

on the advanced tab

i have unticked automatically detect and maintain account settings

ticked allow insecure authentication

all inbound working.

I'm using fasthosts - mailboxes are all starter plus

the outgoing smtp servers are all offline.

if you go to the smtp server list and edit it then there is a "automatically detect and maintain account settings on the advanced tab which i have also unchecked.

there seems to be some confusion on fasthosts support if i should be using smtp.domainname or smtp.livemail.co.uk but i have tried both to no avail.

i have also tried port 25 and 587 with no success.

i have a log active with fasthosts but they are not helping.

any thoughts greatly appreciated. 😕

There is a Fasthosts guide - http://www.yourwebsiteandemail.com/guides/StarterPlus-mailbox-setup-guide.pdf - that suggest that, if you are unable to use port 25 (because, perhaps, your own ISP is blocking port 25) you should change it to 587. Hope that helps.

PS The guide also suggests that, if you are using an external DNS provider, you should set the SMTP server as 'smtp.livemail.co.uk'. However, I use external DNS (not my ISP's) and I use my own domain in 'smtp.mydomain.org.uk'.