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I have installed an SMTP Server on Windows 2022 to on an internal network. So, outside emails. The server runs, and from another server using both telnet and Powershell I can mimic an email being sent.

The problem I am having issue with is setting up Outlook. I have tried both POP and IMAP and I have entered in the FQDN of the SMTP Server and Port 25. All get back is a message saying it cannot connect to the server, the server reported an error.

I have even set up a second server for outgoing emails, but I am only interested in incoming emails from SMTP Server.

The firewalls have been set to allow connections from on the server.

So, what else do I need to do?

Andy5
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  • You haven't given us nearly enough detail. What SMTP server software? What protocols are enabled? Did you create mailboxes for users? Etc., etc. – joeqwerty Aug 20 '23 at 18:26
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    You need an IMAP server. SMTP is for transmitting e-mails between servers, not e-mail retrieval by clients. – vidarlo Aug 20 '23 at 19:09
  • I installed the SMTP from the add features found on Windows Server 2022. I don't recall there being an IMAP Server. Where is there an IMAP Server installation on Windows Server? Unfortunately, this kind of thing is new to me. – Andy5 Aug 20 '23 at 20:21
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    Generally E-mail is one of the most unforgiving services to host. If you click random things and expect it to work, you're in for a world of hurt. But: Microsoft delivers a mail server system called Exchange. It costs money. There's many other mail services, both on Windows and Linux, but their setup is a *little* bit more complex than checking a checkbox, and you ***need*** to have an idea of what you're doing, and how to configure them. – vidarlo Aug 20 '23 at 22:08

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In short the Microsoft SMTP Service extends IIS with SMTP to provide smtp email transport and deliver mail messages.

It is intended to provide other programs with a mail transport to send e-mail. It will typically relay SMTP messages it receives to external mail servers for external recipients and/or your own MS Exchange server for local deliveries.

It is not intended to receive email and deliver messages to local mailboxes. So it doesn't come with IMAP, POP3 and/or MAPI to check to check such local mailboxes either. (IIRC you should be able to create a Drop folder/directory where messages can be stored but that is not a mailbox and that Drop folder can't be checked with a mail client like MS Outlook for new messages.)

If you want to host local mailboxes and use Microsoft tools, then AFAIK MS Exchange is the typical Microsoft solution.

HBruijn
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Are you deploying a mailbox server for mail delivery on your internal network?

I recommend that you install Exchange Server 2019 on Windows Server, a mail server and calendar server developed by Microsoft specifically to run on the Windows Server operating system. It allows you to send, receive, and manage emails, calendars, contacts, tasks, and other communication items.

You can use the Deployment Assistant to quickly deploy Exchange Server in your organization.

Exchange Deployment Assistant | Migrate mailboxes to Microsoft 365

HuiA
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