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SMTP AUTH for MAC OSX Mail.app

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atifghaffar View Drop Down
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Post Options Post Options   Thanks (0) Thanks(0)   Quote atifghaffar Quote  Post ReplyReply Direct Link To This Post Topic: SMTP AUTH for MAC OSX Mail.app
    Posted: 14 September 2006 at 9:22am
Hello all,

Has anyone a solution for Mac OSX's Mail.app SMTP authentication.
It does not support the LOGIN mechanism.

Is is possible to add PLAIN also as a mech?

thanks in advance
best regards

Atif
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atifghaffar View Drop Down
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Post Options Post Options   Thanks (0) Thanks(0)   Quote atifghaffar Quote  Post ReplyReply Direct Link To This Post Posted: 16 September 2006 at 2:56pm
hasnt anyone seen this one yet?

I have to setup another server to handle these clients. I would prefer if there is only one point of entry.

thanks in advance for some ideas.
best regards

Atif
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Post Options Post Options   Thanks (0) Thanks(0)   Quote WebGuyz Quote  Post ReplyReply Direct Link To This Post Posted: 26 February 2007 at 1:35pm

Aaarrrrggghhhh. Just implemented Auth Login and had no idea how many MAC users I had.

All are failing Auth Login. Did this ever get resolved??? using passwd file method and not LdAP.

 

Thanks!



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Post Options Post Options   Thanks (0) Thanks(0)   Quote LogSat Quote  Post ReplyReply Direct Link To This Post Posted: 26 February 2007 at 10:58pm
Atif, WebGuyz,

We apologize, we missed this posting. Just today with WebGuyz's last entry we realized the problem.

SpamFilter only supports the LOGIN SASL mechanism, we don't support the "PLAIN".

We've just attempted to add PLAIN to the current beta of SpamFilter Enteprise. If either of you would like to use it before we release it, please contact us by email.
Roberto Franceschetti

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Post Options Post Options   Thanks (0) Thanks(0)   Quote WebGuyz Quote  Post ReplyReply Direct Link To This Post Posted: 27 February 2007 at 12:28am

Roberto,

  Don't know if I'm wigging out but a few of the mac users are doing auth login succesfully, at least thats what the SFI log says. The others I have whitelisted their office IP's. Not sure why some are working (or appear to be) I'm not a mac person and have idea on how to even turn one one. Mac are much to complicated for me ;-) Don't have one here to test with. Will try to rope one of my Mac users into doing some testing tomorrow.

Curious if others out there in SFI land have MAC's successfully using Auth Login (password file)

Thanks!

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Post Options Post Options   Thanks (0) Thanks(0)   Quote LogSat Quote  Post ReplyReply Direct Link To This Post Posted: 27 February 2007 at 11:30am
It's possible that the ones *not* working are older clients that do not support the "LOGIN" method of using the AUTH command (which is the most common one.. .strange they would not support it).

In any case, we did add the "PLAIN" one in our current internal beta, and it will thus be available from the next beta we release....
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Post Options Post Options   Thanks (0) Thanks(0)   Quote WebGuyz Quote  Post ReplyReply Direct Link To This Post Posted: 27 February 2007 at 3:58pm

What happens when using PLAIN? Do I still use my DES encrypted passwd list or do I have to create a separate one for my MAC users that does not have encrypted passwords? What does a PLAIN authentication file look like?

I had a choice of using LDAP instead of the passwd file,  but the file was so much easier (didn't have to learn LDAP ;-). I may have to go to LDAP if this gets too messy with the MACS. 

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Post Options Post Options   Thanks (0) Thanks(0)   Quote LogSat Quote  Post ReplyReply Direct Link To This Post Posted: 27 February 2007 at 4:11pm
Nothing changes on your end. The PLAIN is just simply another way for the SMTP client to specify the username/password combination to the SMTP server (SpamFilter in this case). The end result, being the user's ID and password, remain the same. You can still use LDAP, AD, and/or Unix passwd files to authenticate them, nothing changes there.
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Post Options Post Options   Thanks (0) Thanks(0)   Quote WebGuyz Quote  Post ReplyReply Direct Link To This Post Posted: 27 February 2007 at 7:53pm

Great!

How much longer before SFE becomes an official release? Weeks? Days?

Is there anything special that has to be done if I install SFE today and tell it to work in standard mode? Will it pickup the current quarantine DB I have and go? Do I install it like I did previous versions, copy the exe's in to the spamfilter directory and crank it up?

 

 

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Post Options Post Options   Thanks (0) Thanks(0)   Quote LogSat Quote  Post ReplyReply Direct Link To This Post Posted: 27 February 2007 at 8:02pm
As far as we know, judging from the bug reports (or lack of...) the beta seems very stable. For the past month or so the issues were only with the GUI functionality, not with the performance and/or crashes.

We may bring out of beta the current 3.5.3.651 and release it as a release canditate (we'll include the AUTH PLAIN addition in the RC) within a few days.

The only thing slowing down the official release right now is the fact that we're updating the documentation and the website.

For the update, as usual we tried to make everything as easy as possible... Yes, simply overwrite the executables as usual. The new 3.5 version will make quite a few changes in the SpamFilter.ini file, moving some settings from there to separate ini file, but this will all happen automatically (right now SpamFilter is not making a backup of the SpamFilter.ini file, we'd recommend you do that manually). SpamFilter will then un SFI (standard) mode without intervention.

To user SFE, you'll also need to copy the two additinoal sql scripts from the database directory. If you upgrade using the installation program, all this will happen automatically.
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Post Options Post Options   Thanks (0) Thanks(0)   Quote LogSat Quote  Post ReplyReply Direct Link To This Post Posted: 27 February 2007 at 10:54pm
FYI - we've just released beta 652 which has the new AUTH PLAIN support. This is the only change since the previous beta.
Roberto Franceschetti

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Post Options Post Options   Thanks (0) Thanks(0)   Quote WebGuyz Quote  Post ReplyReply Direct Link To This Post Posted: 07 March 2007 at 4:57pm

So at the Mac end, what type of authentication do they use? My choices are None, or Password.

 

Thanks!

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Post Options Post Options   Thanks (0) Thanks(0)   Quote LogSat Quote  Post ReplyReply Direct Link To This Post Posted: 07 March 2007 at 10:48pm
...well, no authentication should revert to "basic" SMTP without using the AUTH extensions, and thus without authentication.
If you specify "password" that should allow them to specify username/password, and hopefully the new AUTH PLAIN will work with older Mac clients.
Roberto Franceschetti

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Post Options Post Options   Thanks (0) Thanks(0)   Quote WebGuyz Quote  Post ReplyReply Direct Link To This Post Posted: 08 March 2007 at 9:55am

Didn't seem to help. I finally had to set up a port for the MAC users and had my firewall redirect it to the SmarterMail server and there they could connect and authenticate. Here is the conversation from Smartermail to my Mac User;

08:38:12 [xx.xx.xx.xx][26824636] cmd: EHLO [xx.xx.xx.xx]
08:38:12 [xx.xx.xx.xx][26824636] rsp: 250-mail01 Hello [xx.xx.xx.xx] 250-SIZE 36700160 250-AUTH LOGIN CRAM-MD5 250 OK
08:38:12 [xx.xx.xx.xx][26824636] cmd: AUTH LOGIN
08:38:12 [xx.xx.xx.xx][26824636] rsp: 334 VXNlcm5hbWU6
08:38:12 [xx.xx.xx.xx][26824636] rsp: 334 UGFzc3dvcmQ6
08:38:12 [xx.xx.xx.xx][26824636] rsp: 235 Authentication successful

Here is the conversation using debug view between the Mac and SFE version you uploaded:

>>EHLO [xxx.xx.xx.xx]
<<250-AUTH LOGIN PLAIN
<<250-AUTH=LOGIN
<<250-8BITMIME
<<250-SIZE 35840000
<<250 HELP

It seems like the Mac doesn't know what to do so it disconnects. No more conversation after SFE sends its info.

 

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Post Options Post Options   Thanks (0) Thanks(0)   Quote LogSat Quote  Post ReplyReply Direct Link To This Post Posted: 08 March 2007 at 11:10am
That is really odd, as it shows that the client is indeed using the AUTH LOGIN command, and not the AUTH PLAIN.

What I do see is that you configured SpamFilter to output an incorrect line in the EHLO response, the one that says "AUTH=LOGIN" This was added to support buggy clients, but is invalid:

;Some older email clients have a bug that requires them to see "AUTH=LOGIN" in the EHLo response rather than "AUTH LOGIN". Set this to 1 to add the incorrect syntax to the EHLO output
AddIncorrectAUTHLOGINEHLOEntry=0


Can you try to go back to the default (which disables the incorrect output) to see if that helps?
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Post Options Post Options   Thanks (0) Thanks(0)   Quote WebGuyz Quote  Post ReplyReply Direct Link To This Post Posted: 08 March 2007 at 12:51pm
The reason I added that was because of this problem and thought maybe it would help. Will try removing it and see if I can talk a Mac user into trying this. They are all mad at me right now ;-)
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Post Options Post Options   Thanks (0) Thanks(0)   Quote WebGuyz Quote  Post ReplyReply Direct Link To This Post Posted: 08 March 2007 at 2:50pm

Roberto,

  My apologies for jumping the gun. The test case works fine after I removed the option:

AddIncorrectAUTHLOGINEHLOEntry=1

What screwed me up was that this entry does not work until you start/stop SF. I was troubleshooting my Mac issue and during the course of troubleshooting made the change above but did not restart SF, thinking that it would get picked up by the regular check of spamfilter.ini like all the other option changes. Not so.

What happened was my customers were at first having problems and I made that change and then I started getting reports that the MAC's were working! I thought the above change made the difference!! More then likely it was arp cache or something like that.

That night we did some OS patches and had to reboot the server. next day, all the Macs were broken again.

What I did not realize is that the reboot forced SF to start using the above option and 'broke' the MAC's.

After I removed it today and realized that it was not changing until I restarted did it dawn on me what happened.

What was worse was I came across that old post about MAC's not working and made the wrong assumptions.

Sometimes I think I'm my own worst enemy .....

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Post Options Post Options   Thanks (0) Thanks(0)   Quote LogSat Quote  Post ReplyReply Direct Link To This Post Posted: 08 March 2007 at 4:08pm
Darn, that actually is practically the *only* setting in SpamFilter that requires a restart of SpamFilter (with the exception of the listening IP/port, unless changed via the GUI)... Sorry! I thought I had documented that somewhere...

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Post Options Post Options   Thanks (0) Thanks(0)   Quote WebGuyz Quote  Post ReplyReply Direct Link To This Post Posted: 08 March 2007 at 4:49pm
You probably did. You should update that info on that option and mention that if they use it their Mac's will stop working.
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Post Options Post Options   Thanks (0) Thanks(0)   Quote jemmie Quote  Post ReplyReply Direct Link To This Post Posted: 28 April 2007 at 12:31pm

Hi all,

I still have a problem to send mail from a mac with mail.app. When I send mail the log file from SFI show only the next two line:

04/28/07 17:02:33:189 -- (8448) Connection from: XX.XX.XX.XX  -  Originating country : Netherlands
04/28/07 17:02:33:209 -- (8448) Disconnect

The debug view shows the next lines:

>>EHLO [XX.XX.XX.XX]

<<250-AUTH LOGIN PLAIN

<<250-8BITMIME

<<250 HELP

When I try on the same mac to send mail from entourage there is no problem.

I am using version 3.5.3.662 in standard mode.

The version of the mac os is also the latest, 10.4.9, and mail.apps is version 2.1

Is there a difference between the enterprise mode and the standard mode that can cause this or does anyone have any other suggestion

Thanks already,

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Post Options Post Options   Thanks (0) Thanks(0)   Quote WebGuyz Quote  Post ReplyReply Direct Link To This Post Posted: 28 April 2007 at 10:13pm

250-AUTH LOGIN CRAM-MD5 250 OK

I believe the issue is the bolded above. This is what I get when my MAC's attempt to login to our Smartermail server and are successful.

I don't think it was PLAIN that needed to be added, but rather CRAM-MD5.

But I don't know for sure...


 

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Post Options Post Options   Thanks (0) Thanks(0)   Quote LogSat Quote  Post ReplyReply Direct Link To This Post Posted: 28 April 2007 at 10:46pm
We not support CRAM-MD5 yet, sorry...
Roberto Franceschetti

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