



Thank you for your response. I commented on this thread (instead of start a new one) because I am facing the exact same issue as lamclennnan. I believe you might have seen me say this in an earlier comment. I think my words were, "facing the exact same issue".





FWIW, I think lamclennnan summed up the issue perfectly in this comment:

Thanks. I already have gmail added to windows live mail on my local PC. That is not the issue and I can send from my local PC because I can meet the requirements which a cloud service cannot. The issue is that gmail cannot authenticate to the outlook.com SMTP because it is not trusted when sending emails. Asks gmail to login via http which is not possible on any cloud service.





And then again for the benefit of your esteemed colleagues:

Thank you for your response. I actually have the opposite setup. So outlook forwarding to gmail and gmail sending as outlook.com. As you can see from what I have previously posted there is an issue with the security settings on my account. It will not let gmail or any other unknown address (such as checktls.com) fully authenticate without first logging in via a web browser which is not possible with most cloud services. Regards.





And yet again here:

Thank you for your response. However, you're not reading what I have posted here. I have all that setup already. It has been working for sometime. The issue is I cannot authenticate to smtp.live.com now because it is asking I login via a web browser first which is not possible with gmail and most cloud services(as opposed to it being possible on my PC). I've done the troubleshooting already and posted here. What I require is some action from an outlook/microsoft employee to disable this 2nd step which is impossible in this situation. I have of course confirmed that two step authentication is off.





Now, as I'm sure we're not here to admire my ctrl+c, ctrl+v talents, I shall attempt to describe this same issue lamclennnan has reiterated multiply above, sans any big words and technical jargon lest it confuses anyone.





It all began when someone at Microsoft decided it just wasn't proof enough of someone's identity to be able to simply furnish one's email address and password over a TLS/SSL connection. 'No!', cried the security expert. 'We can't allow just anyone with the email address and password to send messages over SMTP! To provide proof beyond all doubt, let's insist they provide the exact same credentials over HTTPS too!"





And so it was. From then on, anyone who tried to set up a desktop email client (like Thunderbird) saw this error message, 535 5.2.1 Login to your account via a web browser to verify your account. (SMTP AUTH failed with the remote server), and could admire this security expert's handiwork. After a suitable period of admiration, typically about 15 minutes (inclusive of the time it takes to google said error message), they would fire up a desktop browser (like Chromium) and log in with the same credentials they provided over SMTP. Lo and behold, now SMTP works, fantastic security feature! Can't believe no one thought of it sooner!





All was well for a time, then came Beefcake. Beefcake is a true plebeian, down to his poor taste in browser-based email clients. As a result of this, he prefers gmail.com's user interface over live.com's. So he set up his Hotmail account, *** Email address is removed for privacy *** (which he's had for a much longer time than Gmail), to forward all incoming messages to *** Email address is removed for privacy ***.





That worked fine for receiving emails, but all of Beefcake's cool friends use @hotmail, @live.com or outlook.com email addresses. He needed to mask the fact that he was, in fact, using Gmail, so his cool friends wouldn't think any less of him. So he went and tried to set up Gmail's 'Send mail as' feature, designed for just such a purpose.





535 5.2.1 Login to your account via a web browser to verify your account. (SMTP AUTH failed with the remote server), as seen Beefcake may not know much about the internet, programming, SMTP or other spiffy acronyms, but he knew the 'Send mail as' feature makes Gmail authenticate with an intended SMTP server and forwards the message, such that the eventual recipient may see our intended SMTP server as the origin of the message. But after entering all the required details, he got this error message,, as seen here . Now,may not know much about the internet, programming, SMTP or other spiffy acronyms, but he knew the 'Send mail as' feature makes Gmail authenticate with an intended SMTP server and forwards the message, such that the eventual recipient may see our intended SMTP server as the origin of the message.





Now, Beefcake could file a bug report against Gmail, so they can rewrite their 'Send mail as' code to authenticate over HTTPS prior to connecting to the SMTP server. But he knows that the Microsoft team is much cooler, and after all, all his cool friends use Microsoft emails for a reason right? So he thought he'd ask for help in Microsoft's community forums.





And that leads us here. Hope this is sufficient information to go on towards resolving this issue and thanks in advance!





Cheers,

Beefcake

Hi