Failed Authentication for SMTP

[Carl Springer]

Tried installing a personal certificate to digitally sign message. Never got it
in right -- that is another post someday -- but now I am stuck with the
following error messages when sending:

"Authentication failed because Entourage doesn't support any of the
available authentication methods."

Going to the Accounts dialog, there is no certificates checked under the
Security tab, so I am baffled why it is 'failing'. I tried trashing preferences to
Entourge, deleting the digital certificates with no good results.

Question is: how do I go back to not no authentication check? Do I just re-
install Entourage?

 

[Chris Ridd]

Tried installing a personal certificate to digitally sign message. Never got
it
in right -- that is another post someday -- but now I am stuck with the
following error messages when sending:

I managed to get signing and encryption working, though it isn't very well
described in the online help. I even got it reading people's S/MIME certs
out of an LDAP directory

"Authentication failed because Entourage doesn't support any of the
available authentication methods."

Going to the Accounts dialog, there is no certificates checked under the
Security tab, so I am baffled why it is 'failing'. I tried trashing
preferences to
Entourge, deleting the digital certificates with no good results.

Question is: how do I go back to not no authentication check? Do I just re-
install Entourage?

The certificates/keys you configure under the account/security settings
aren't used to authenticate you to your POP/IMAP/etc server.

The POP/IMAP/etc auth settings are in the account/account settings screen,
when you click the "Click here for advanced [...] options" buttons. Try
changing the "Always use secure password" setting - I believe that switches
between some proprietary MS authentication mechanism and standard ones.

Cheers,

Chris

 

[Carl Springer]

The POP/IMAP/etc auth settings are in the account/account settings screen,
when you click the "Click here for advanced [...] options" buttons. Try
changing the "Always use secure password" setting - I believe that switches
between some proprietary MS authentication mechanism and standard ones.

Cheers,

Chris

Chris - That had no effect. That is a POP setting for retrieving email,
which works fine. It is the sending (SMTP) that has been impacted.

Perhaps I can go the other way; trying to re-install the signing certificate
-- I had a similar experience with very limited Help from Entourage. Any
hints or tips to configuring the signing certificate?

I bought one for $15, but had no clue how to install it. It ended up on my
MacOS keychain, and I could never 'select' it in Entourage under the
Accounts > Security settings.

Any help would be appreciated.

 

[Chris Ridd]

The POP/IMAP/etc auth settings are in the account/account settings screen,
when you click the "Click here for advanced [...] options" buttons. Try
changing the "Always use secure password" setting - I believe that switches
between some proprietary MS authentication mechanism and standard ones.

Cheers,

Chris

Chris - That had no effect. That is a POP setting for retrieving email,
which works fine. It is the sending (SMTP) that has been impacted.

There are two buttons in the screen I mentioned - one for POP/IMAP and one
for sending SMTP. The SMTP one doesn't have the "Always use secure password"
setting, but it is worth reviewing to make sure the settings are correct. I
can't think what else might be going wrong here...

Perhaps I can go the other way; trying to re-install the signing certificate
-- I had a similar experience with very limited Help from Entourage. Any
hints or tips to configuring the signing certificate?

I bought one for $15, but had no clue how to install it. It ended up on my
MacOS keychain, and I could never 'select' it in Entourage under the
Accounts > Security settings.

OK, I got a free one from Thawte and what happened was that eventually you
download the certificate and private key in a single file using your web
browser. Then start Keychain Access.app, make sure you've selected the login
keychain (the open keychains are listed in the window drawer) and go to
File>Import. Choose the file you just downloaded. You should be prompted for
a password to decrypt the file.

Once imported, you should see two new items in Keychain Access - one
certificate and one private key. Eg "Thawte Freemail Member" for the
certificate and "Key from www.thawte.com" for the private key. I see two
more new items as well. When you go to select a signing certificate in
Accounts/Security in Entourage, the popup menu will list all the names of
certificates with private keys, eg "Thawte Freemail Member". If you can get
this far, it should be straightforward to actually sign and encrypt emails

Any help would be appreciated.

Cheers,

Chris