Difficulties sending emails from my Gmail account using my Outlook.com SMTP

Patrick B. G. · 12. November 2024

Dear Community,I am experiencing difficulties sending emails from my Gmail account using my Outlook.com SMTP server. I have already tried the following troubleshooting steps:Used an app-specific password for authentication.Verified the SMTP settings: smtp-mail.outlook.com or outlook.office365.com, port 587, TLS.Disabled and enabled POP3 in my Outlook.com account.Ensured the correct username full Outlook.com email address and password.Despite these efforts, I continue to receive the following error message: "Server error: "334 VXNlcm5hbWU6 334 UGFzc3dvcmQ6 535 5.7.139 Authentication unsuccess

Rasika murkar

I didnot install office on my laptop. It had come with preinstalled office 365 apps.
I received the purchase confirmation from lenovo germany on my gmail id (which is actually from India)
I have actually used the student discount while purchaseing the laptop using my university email id to get discount and while billing I gave my indian gmail id.
I am using the same indian gmail id for logging in to my microsoft account for activating the office on my laptop. I also tried asking for help on lenovo support but they say to ask microsoft support to give product key or activation help. I also asked microsoft but I get no response.

WolfgangTichy

noch als Zusatzinfo:

Additional info:

I ran the following test:

I took a .docx file I created on my office PC which was stored on our server and saved it locally to my PC harddrive. I then save a copy as .doc as well. Then I emailed both files to my office Outlook account AND my iCloud account (with one email).

BOTH files did NOT open from my Outlook account and BOTH files just opened fine from my iCloud account.

I then forwarded the email from my Outlook account to my iCloud account and now BOTH files did NOT open anymore.

So it seems that my Outlook account (Exchange server) corrupts the files.

Can that be?

best regards

Wolfgang

StephanGK

Hi Diane,
 Thank you so much! I thought all my data was stored locally in my .pst file, but apparently Outlook did use a Microsoft Exchange Server. I logged on to Outlook Live through my regular Microsoft account, using an email address that is neither a Hotmail nor an Outlook.com address. But when I am logged on to Outlook Live, it does show an outlook.com address, which I don't remember ever creating and which consists of seemingly random letters and numbers. Now I don't know how to add this account to my local Outlook...

Wolferl85

Hi Neil,
 it looks like your suggestion has worked. It did however not solve the3 problem of my lost Outlook 2016 account, but via Outlook.com by Browser, I can get my mails from my yahoo mail, with all my existing folders and rules.
 Thanks and kind regards,
 Wolfgang

Georgi T.

Hallo Andreas,

Hier ist die Antwort auf deine Frage:

https://blogs.msdn.microsoft.com/tz...ard-from-my-outlook-com-account-get-rejected/

Bedanke mich für dein Verständnis.

Mit freundlichen Grüßen,

Georgi Taskov

Microsoft Office 365 Support Engineer

Wenn Sie das hilfreich finden, bitte markieren sie es als "Hilfreich" oder "Antwort".

Hi,

willkommen im Windows Forum!

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