Is it possible to use Google App Password for Opera Mail on Windows as a means for 2-step verification process required to access Gmail via VPN servers?

I also read on one VPN provider site, it may be related to Mail Client not supporting proper TLS login protocol version or such

Opera Mail has really good support for TLS, so I doubt that as anything to do with it. But if you wanted to, in Opera Mail's operaprefs.ini (see "Menu -> Help -> About Opera Mail" for the location), while Opera's closed, you can explicitly turn on TLS 1.1 and 1.2 (and 1.0 for that matter) to make sure they're on (as opposed to accepting the defaults, which should be all of them on). In short, it shouldn't make a difference, but you can try.

[Security Prefs]
Enable TLS v1.0=1
Enable TLS v1.1=1
Enable TLS v1.2=1

(You add the "Security Prefs" section if it's not there.)

@zamar27 said in Opera Mail setup through VPN:

I tried several Windows VPN clients, and Opera Mail can't check mail if any of them is enabled, or a router OpenVPN client is On.

I think Opera Mail uses its own network stack and only supports connecting directly. When you turn a VPN on for Windows, Opera won't make use of it and will try to connect to the sever directly, which it can't do as to it, it's kind of like your connection is down. But, not completely sure.

@zamar27 said in Opera Mail setup through VPN:

I'll need to ask whether the VPN provider supports IMAP/POP and SMTP traffic

Good idea.

router also runs OpenVPN client, and all router internet traffic goes through a VPN provider?

I don't know for sure, but I think if you have a router that supports VPN client mode, you can set up your router to connect right to the vpn so that all the traffic (including Opera Mail's) going through the router goes through the VPN. That depends on the router though. In this setup, you wouldn't have to do anything to Opera Mail. It'd just work (assuming your VPN supports IMAP/POP and SMTP traffic).

@zamar27 said in Opera Mail setup through VPN:

Would you care to explain, why Socks 5 proxy is needed to connect a Mail Client through VPN

@zamar27 said in Opera Mail setup through VPN:

why Socks 5 proxy is needed to connect a Mail Client through VPN

I'm not sure why it's typically done via a socks proxy instead of directly. That's just what programs usually support.

On a side, I think you can set up a VPN for Windows. But, I'm not sure it'll affect Opera Mail. It should affect Internet Explorer and other programs that use the Windows network stack.

Thanks for the exhaustive and concise reply beyond typical one phrase forum expectations. Yeah, its probably time to pack all much loved toys in the closet. Would you care to explain, why Socks 5 proxy is needed to connect a Mail Client through VPN, since I'm and most other Opera users might not be that familiar with VPN technicalities?

If such Socks proxy feature is available on a router, would it be possible to connect Opera Mail through that proxy, while the router also runs OpenVPN client, and all router internet traffic goes through a VPN provider?

However, you can use Opera 12 just for mail if you want. In "Alt + P -> advanced -> Programs", you can add/set http and https to "open with default application" so that links in emails open in your default browser. The bonus to doing that is opera:config is available and all the settings are still there in preferences.

If you still like using Opera Mail, you can make changes to preferences in Opera 12, close Opera 12 and look at operaprefs.ini (see opera:about for the location). You can then duplicate the settings you want in Opera Mail's operaprefs.ini.

Anyway, in Opera 12, you can connect to a VPN through a Socks5 proxy. "Alt + P -> Advanced -> Network -> Proxy Servers". You can then toggle the proxy via F12. If I remember correctly though, the downside is that the proxy only works for the browser part. The Opera Mail part will still connect directly. This also means that copying over the proxy settings to the standalone Opera Mail program won't have any effect.

The only option you have is to use incoming and outgoing mail servers in Opera that act as a proxy to the VPN and then to the real mail servers. Besides that, you're out of luck.

With Thunderbird though, you can connect to a VPN through Socks and it'll work for the mail connections. Sylpheed and Claws Mail might be able to do that too, but I don't remember.