Outlook when connecting to Exchange passes freely proxies (the main thing that used authenticated). Because it uses https.
If you use Outlook to connect to the yandex/mail/gmail - the answer how to force Outlook to work via a proxy will in any way. (not the issues of port forwarding, ssh port forwarding, and other things, if a person asks a question on the toaster - it is unlikely in the next five years he mastered).
There are two options:
* Abandon the client in favor of web muzzle
* Ask the administrator to open a direct connection (configure NAT) on ports 143, 110, 25 (underline) to the desired resource yandex/mail/gmail (underline)
If you use Outlook to connect to the yandex/mail/gmail - the answer how to force Outlook to work via a proxy will in any way. (not the issues of port forwarding, ssh port forwarding, and other things, if a person asks a question on the toaster - it is unlikely in the next five years he mastered).
There are two options:
* Abandon the client in favor of web muzzle
* Ask the administrator to open a direct connection (configure NAT) on ports 143, 110, 25 (underline) to the desired resource yandex/mail/gmail (underline)