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problems getting ssl to work with specific email address-help

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Hi, here is the goal: outlook 2010 is interfacing with a server running web mail; there is a digital certificate installed on the web server; there are 3-email accounts to be defined within outlook (all are defined on the web mail account); 2 of the outlook accounts (non-encrypted) work fine.  The 3rd account, which needs to be encrypted (secure email from sender to receiver...including response from receiver back to sender) follows the same 'auto account setup process' as the earlier added other 2-accounts; the email address and password that are defined on the web mail account are cut/pasted into their respective areas on the outlook 2010 'auto account setup' panel; 'manually configure setup' option is not checked; 'next' is clicked; the 'online search for server settings' panel appears and we established a network connection; then an error message appears that states 'an encrypted connection to your mail server is not available. click next to attempt using an unencrypted connection'.   when 'next' is clicked, the account is added. this process works and the message 'your imap email account is successfully configured'. 

then I delete the account just setup so i can re-add it using the manually configured setup; here is what happens after the initial panel is completed and this option is checked; the 'add new account' panel appears, the 'internet e-mail' option is clicked; 'next' is clicked; the 'internet email settings' panel appears; my name is filled in; my email address for the new account is cut/pasted in (same as defined on web mail account running on the server); imap is selected; the name of the incoming email server is cut/pasted in (same for the outgoing mail server;  in the log-in section...name box, I enter the email address that will be used for this account (same as what was entered above); then the password for this email address is cut/pasted in to the password entry box; 'remember password' box is checked; 'require logon using secure password authentication (spa) is checked;'more settings' is then clicked;

  'advanced' tab is clicked; incoming imap server is set to 995; ssl is selected from the drop down box; outgoing smtp server port '465' is selected; and 'ssl' is selected from the next drop down box; then 'ok' clicked; then 'next' is clicked (internet email settings panel); then 'next' is clicked; the following error message appears: Send test e-mail message: "Your server does not support the connection encryption type you have specified. Try changing the encryption method. Contact your mail server administrator or Internet service provider (ISP) for additional assistance."

the mail server administrator swears everything is setup correctly. 

Comments on resolving this please.

I did go back and change the setting from 'ssl' to 'auto' in each of the drop down boxes, and the test works; when i send an email with the newly setup account, the receiving account does not show 'https'...

i need some direction on getting the installation issues for an email address that wil be encrypted for both the sender and receiver resolved. Comments please.



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