How to forward messages from hotmail to gmail?

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How to forward messages from hotmail to gmail?

Hans 25

Hello,

I used to be able to forward messages from hotmail to gmail for years, but it has stopped working.

Below is my setup in Outlook to enable POP:
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Below is the error message I got when I try to set up in Gmail to read email from hotmail:

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I wonder if anyone has the same issue and how to get this work? Thank you very much for your time!

Hans

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Answer 1

Harold Milan 10,390 Independent Advisor

Hi Hans,

The error message in Gmail says:

“There was a problem while connecting to outlook.office365.com. Please contact Microsoft’s Support Team for more information on POP access.”

This means Gmail can’t connect to your Hotmail account using POP. Common reasons include:

Microsoft tightened security for older protocols like POP and SMTP.

Two-step verification is enabled, so your normal password won’t work for POP you need an app password.

Server settings have changed Gmail expects outlook.office365.com for POP, but authentication fails without the correct credentials.

Here’s How you can try to Fix It

Generate an App Password

Go to https://account.live.com/proofs/manage .

Under App passwords, create a new one.

Use this app password instead of your regular password in Gmail.

Confirm POP Settings

POP Server: outlook.office365.com

Port: 995

SSL: Enabled

Username: Your full Hotmail email address.

Enable POP in Outlook.com

In your screenshot, POP is already enabled that’s good.

Make sure “Let devices and apps use POP” is turned on.

Consider Switching to IMAP

IMAP is more reliable and supported long-term.

IMAP Server: outlook.office365.com, Port: 993, SSL enabled.

SMTP Server: smtp.office365.com, Port: 587, STARTTLS enabled.

Update Gmail Settings

In Gmail, go to Settings > Accounts and Import > Add a mail account.

Enter your Hotmail address, then use the app password and correct server settings.

If POP still fails after using an app password, switch to IMAP it’s the recommended method now. IMAP keeps your folders synced and avoids issues with Microsoft’s newer security policies. Let me know how it goes, Happy to help!

Hans 25 Reputation points

2025-11-12T01:00:06.6266667+00:00

Hi Harold, thanks so much for your answer. I don't have two-step verification. There is no IMAP options from Gmail when I setup, only POP3 and Gmaily option are available. Do you think I can use the IMAP server in the screenshot that I posted for Gmail setup after choosing POP3? I can try that if this is what I am supposed to do. Thanks a lot! Hans
Harold Milan 10,390 Reputation points Independent Advisor

2025-11-12T14:46:04.7+00:00

Hi again,

What You Can Do Instead

Continue with POP using an App Password Even if you don’t have two-step verification now, enabling it and creating an app password often resolves POP authentication issues.

Use Gmail’s “Send mail as” + Outlook Forwarding

Keep forwarding enabled in Outlook as shown in your screenshot.

In Gmail, set up “Send mail as” for your Hotmail address under Settings > Accounts and Import.

This way, Gmail receives forwarded mail and can reply using your Hotmail identity.

Use Outlook.com in Gmail via IMAP in a Mail Client If you want full IMAP sync, you’ll need to use a mail client like Outlook or Thunderbird instead of Gmail’s fetcher.

Since Gmail doesn’t support IMAP for external accounts, the best solution is to stick with POP using an app password or use forwarding plus “Send mail as” for a seamless experience.
Hans 25 Reputation points

2025-11-14T14:58:19.63+00:00

Thanks so much, Harold, for your further response. I am not going to enable two-step verification for now. I found that the forwarding works some external emails including job boards and other larger companies. It doesn't work for my current company, i.e. whenever an email from ***@mycompany.com sent to ***@hotmail.com, ***@mycompany.com will received below:

And it will not appear in my Gmail. If enabling two-step verification is my only solution now. I will accept this answer and decide on that later.

Thank you!
Hans
Harold Milan 10,390 Reputation points Independent Advisor

2025-11-14T15:00:43.3333333+00:00

I'm really glad if this helped you out! If you found the information useful, Happy to help!
Hans 25 Reputation points

2025-11-14T15:08:52.8933333+00:00

Thanks Harold, I really wanted to forward emails from ***@mycompany.com to ***@hotmail.com, to Gmail because now whenever a co-worker send an email to my hotmail, they will get the bounced back message that I attached in my previous message. Please let me know if anyone has any ideas. Thank you very much!

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