Email Setup

FreePBX System Administration
1

I manage several PBX systems and some of them the email works fine and some don’t/ After quite a bit of comparing settings and troubleshooting, I am unable to come up with a definite answer.

Does anyone have a solid solution using internal or external server for email with FreePBX?

2

Are you using SysAdmin Pro? The Debug should tell you what’s wrong. There’s also a 30-day free trial if you haven’t yet tried it.

3

Yes all of my systems are running Admin Pro. And I look at the debug output and someeimtes it will give you good info and sometimes not.

Below is an example form a PBX set the same as others and according to this output the message should have been sent but it never arrives.

2026-08-08T14:53:20.727254-04:00 pbx3 postfix/pickup[653902]: B1760C80854: uid=999 from=<asterisk>
2026-08-08T14:53:20.731996-04:00 pbx3 postfix/cleanup[659107]: B1760C80854: message-id=<[email protected]>
2026-08-08T14:53:20.754264-04:00 pbx3 postfix/qmgr[653903]: B1760C80854: from=<[email protected]>, size=436, nrcpt=1 (queue active)
2026-08-08T14:53:20.849992-04:00 pbx3 postfix/smtp[659109]: connect to datacare-co.mail.protection.outlook.com[2a01:111:f403:c931::1]:25: Network is unreachable
2026-08-08T14:53:21.605275-04:00 pbx3 postfix/smtp[659109]: B1760C80854: to=<[email protected]>, relay=datacare-co.mail.protection.outlook.com[52.101.10.16]:25, delay=0.91, delays=0.06/0.01/0.2/0.64, dsn=2.6.0, status=sent (250 2.6.0 <[email protected]> [InternalId=45513768449913, Hostname=IA3PR03MB7642.namprd03.prod.outlook.com] 9590 bytes in 0.133, 70.045 KB/sec Queued mail for delivery)
2026-08-08T14:53:21.606003-04:00 pbx3 postfix/qmgr[653903]: B1760C80854: removed
4

We could end up going down all sorts of rabbit holes when it comes to email deliverability. Are the systems all using Outlook? What’s different and what’s the same about them?

Use something like this to see if something is wrong: Email Deliverability Tool - Check Your Deliverability Report - MxToolBox

Also check the Sender address in three places:

System Admin > Notification Settings > From Address

Voicemail Admin > Settings > Email Config

Advanced Settings > Email “From:” Address

When I have come up against issues such as this, the first thing I do is use a known good email account to establish whether it’s the PBX or the way I’ve set things up.

Some providers are more fiddly than others. Getting email to just work will never not be satisfying! It seems that whenever it gets easier, recipient standards get harder to meet. MxToolbox is very useful.

Lastly, check you’re allowed to send mail over typical SMTP ports like 25, 465, 587. These ports are blocked by DigitalOcean, for example, and nothing you try will get round it. You need to use a mail relay service such as SMTP2GO, sending on port 2525 with TLS encryption and SASL authentication.

In the example you’ve posted, the PBX is successfully connecting on port 25 and the message is being accepted upstream, so that isn’t the problem on this system. For any of the others where email is failing, it’s still worth checking whether your hosting provider blocks outbound SMTP.

5

On the systems that work I have it set ot use an internal mail server and have the FQDN of hte pbx set adnd in DNS I have created a A ricord for the fqdn that points to the pbx. Several of those seem to work.

On a recent one that does not, I have been trying to get it to work with our iRedMail server we ue for notifications from several systems.

Debug looks like this:

2026-08-09T15:12:48.054715-04:00 pbx postfix/pickup[2837519]: 0D3C7C0E51: uid=999 from=<asterisk>
2026-08-09T15:12:48.060679-04:00 pbx postfix/cleanup[2837570]: 0D3C7C0E51: message-id=<20260809191248.0D3C7C0E51@laketitlepbx>
2026-08-09T15:12:48.062418-04:00 pbx postfix/qmgr[2837518]: 0D3C7C0E51: from=<[email protected]>, size=430, nrcpt=1 (queue active)
2026-08-09T15:12:48.655770-04:00 pbx postfix/smtp[2837572]: 0D3C7C0E51: to=<[email protected]>, relay=mail.datacareadvanced.net[50.224.130.60]:587, delay=0.62, delays=0.03/0.02/0.52/0.05, dsn=5.1.0, status=bounced (host mail.datacareadvanced.net[50.224.130.60] said: 550 5.1.0 <[email protected]>: Sender address rejected: User unknown (in reply to RCPT TO command))
2026-08-09T15:12:48.693784-04:00 pbx postfix/cleanup[2837570]: A93DDC0E84: message-id=<20260809191248.A93DDC0E84@laketitlepbx>
2026-08-09T15:12:48.696200-04:00 pbx postfix/bounce[2837574]: 0D3C7C0E51: sender non-delivery notification: A93DDC0E84
2026-08-09T15:12:48.696315-04:00 pbx postfix/qmgr[2837518]: A93DDC0E84: from=<>, size=2536, nrcpt=1 (queue active)
2026-08-09T15:12:48.696682-04:00 pbx postfix/qmgr[2837518]: 0D3C7C0E51: removed
2026-08-09T15:12:49.609427-04:00 pbx postfix/smtp[2837572]: A93DDC0E84: to=<[email protected]>, relay=mail.datacareadvanced.net[50.224.130.60]:587, delay=0.92, delays=0/0/0.87/0.04, dsn=5.1.1, status=bounced (host mail.datacareadvanced.net[50.224.130.60] said: 550 5.1.1 <[email protected]>: Recipient address rejected: User unknown (in reply to RCPT TO command))
2026-08-09T15:12:49.644512-04:00 pbx postfix/qmgr[2837518]: A93DDC0E84: removed

Also I have the address set to [email protected] in all 3 of the following:

System Admin > Notification Settings > From Address

Voicemail Admin > Settings > Email Config

Advanced Settings > Email “From:” Addres s

6

This is the sender and it’s being rejected. Ensure that’s a real mailbox or at least a forwarder, and change the Sender/From in all three places mentioned.

7

When you say the email does not work. What exactly are you referring to ?

  • the system never sends the email out ?
  • or the email is sent but the receiver never gets it ?

I looked up your email addresses on MXTOOLBOX (you really should not put peoples email in public view, fyi, this is not a secure site) The FROM address datacareadvanced.net was blacklisted

  • “If you are on the UCEPROTECTL2/L3, you have an IP address from your ISP that falls into a poor reputation range (i.e., the entire range of IP addresses is blocked as a result of the provider hosting spammers)”

We had a client that I set up their FreePBX System, and Microsoft just flat out refused to accept the emails from them from that system. We run our own email server at our place and what I ended up doing was creating accounts on our server for their 5 staff (dummy accounts), then forwarding everything that comes in directly to their email account hosted with microsoft. Basically creating a relay service, then auto deleting everything we forwarded.

Not the ideal way to do it, but it was a quick fix that worked.

So first thing I would do is test and verify emails to yourself from their server to see if you get them. You can verify they are going out and that “someone” can receive them. Verify the server you are using to send from is still not blacklisted someplace,

let us know what you find

8

One thing worth adding to the checklist above: if the systems that fail are on different hosts/IPs, check the reverse DNS (PTR) record for each sending IP and make sure SPF/DKIM actually align with the domain in the From address. Postfix will happily accept and relay the message locally (which is why the log looks fine), but the receiving mail server can silently drop it later in its own filtering if the PTR doesn’t resolve or SPF fails, with no bounce ever coming back to the PBX. Comparing “dig -x ” output between a working box and a failing one is usually a quick way to spot the difference.