Entourage smtp authentication problem

[dan]

I am running Entourage 10.1.6 on my MacBook Pro (OS 10.4.10) and am
having problems sending out email. My ISP has just changed our SMTP
settings to:

Using SSL
Over-riding defaut SMTP port: 465
Using authentication with my username and password.

The problem is that when I first send an email, all works well. but If
I want to send a second email, I get the following Entourage error
message:

Error: Mail cannot be sent using this account...
Explanation: Security failure. Data decryption error.

Help. It is obviously such a pain to constantly restart entourage
everytime I want to send email.
Oh, do add insult to injury, my ISP (ATT) does not support
Entourage....

Any advice would be much appreciated. Thanks, Dan

 

[Diane Ross]

I am running Entourage 10.1.6 on my MacBook Pro (OS 10.4.10) and am
having problems sending out email. My ISP has just changed our SMTP
settings to:

Using SSL
Over-riding defaut SMTP port: 465
Using authentication with my username and password.

The problem is that when I first send an email, all works well. but If
I want to send a second email, I get the following Entourage error
message:

Error: Mail cannot be sent using this account...
Explanation: Security failure. Data decryption error.

Help. It is obviously such a pain to constantly restart entourage
everytime I want to send email.
Oh, do add insult to injury, my ISP (ATT) does not support
Entourage....

Any advice would be much appreciated. Thanks, Dan

Entourage X is now "end of life" the latest update is 10.1.9 which I suggest
you download and install. Entourage X is also not Daylight Saving Time
compliant. There is a workaround that you need to apply.

<http://www.entourage.mvps.org/articles/unofficial_dst_workaround.html>

It's possible that the new security update your ISP just installed is
related to the DST issue. I know Hotmail broke for Entourage X users because
of this issue.

 

[dan]

thanks for the advice. I did run the 10.1.9 update - but Entourage
remains at 10.1.6 - is that normal?
I also changed the timezone file - but still having problems. Do you
know of any issues regarding how entourage handles encrypted data?
Dan

 

[dan]

thanks for the advice. I did run the 10.1.9 update - but Entourage
remains at 10.1.6 - is that normal?
I also changed the timezone file - but still having problems. Do you
know of any issues regarding how entourage handles encrypted data?
Dan

 

[dan]

thanks for the advice. I did run the 10.1.9 update - but Entourage
remains at 10.1.6 - is that normal?
I also changed the timezone file - but still having problems. Do you
know of any issues regarding how entourage handles encrypted data?
Dan

 

[Diane Ross]

thanks for the advice. I did run the 10.1.9 update - but Entourage
remains at 10.1.6 - is that normal?

No. This sounds like what some users are experiencing with 2004 not finding
the files to update. The problem is in your system files that are used by
Entourage. You will need to apply the combo updater to see if that helps and
if not, do an "Archive & Install".

I also changed the timezone file - but still having problems. Do you
know of any issues regarding how entourage handles encrypted data?

Your question about encrypted data is too vague to reply. Please be more
specific.

 

[dan]

Diane,
Where do I get the combo updater for Entourage (OS X)? If not that,
how do I do an archive and install? I don't see any of these options
with the current updater. I'm hoping that the update will fix some of
the issues I am experiencing.

My question re: encrypted data refers to my original problem -
Entourage has no problem sending my first email using ssl and via
authenticated smtp - but when I try to send another email, I get the
"data encryption error" message and cannot send any further emails
until i restart Entourage. Seems like Entourage gets the encrypted
data correct to send the first email - but somehow does not empty that
encrypted info out of its cache and cannot move forward with
conducting another email sending...

help!

 

[Diane Ross]

Where do I get the combo updater for Entourage (OS X)? If not that,
how do I do an archive and install? I don't see any of these options
with the current updater. I'm hoping that the update will fix some of
the issues I am experiencing.

The combo updater is the Apple combo updater. Combo updaters will install on
the same version as they¹re applying‹no need to roll back or do a clean
install.

Mac OS X 10.4.10 Combo Update (PPC)
<http://www.apple.com/downloads/macosx/apple/macosx_updates/macosx10410combo
updateppc.html>

Mac OS X 10.4.10 Combo Update (Intel)

<http://www.apple.com/downloads/macosx/apple/macosx_updates/macosx10410combo
updateintel.html>

More info on why applying the combo updater helps:

<http://www.entourage.mvps.org/troubleshoot/combo.html>

If it fails there, do an "Archive and Install" of the OS. "Archive and
Install" moves existing system files to a folder named Previous System and
then installs Mac OS X again.

Just be sure to check Preserve Users and Network Settings when you select
Archive & Install.

Mac OS X: About the Archive and Install feature

<http://docs.info.apple.com/article.html?artnum=107120>

Archive and Install of the OS

<http://www.entourage.mvps.org/glossary/archive_install.html>

General advice on performing an Archive and Install

My question re: encrypted data refers to my original problem -
Entourage has no problem sending my first email using ssl and via
authenticated smtp - but when I try to send another email, I get the
"data encryption error" message and cannot send any further emails
until i restart Entourage. Seems like Entourage gets the encrypted
data correct to send the first email - but somehow does not empty that
encrypted info out of its cache and cannot move forward with
conducting another email sending...

Much clearer. This is not a usual situation so regrettably I have no
suggestions other than monitor your network traffic to see what is going on
behind the scenes. Test your network with tcpflow. See directions here:

<http://www.entourage.mvps.org/troubleshoot/tcpflow.html>

Let me know if the combo updater helps.