SMTP Email notifications fail in 4 out of 27 pfSenses
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- Are those "sender email addresses" properly configured on the Office 365 side? 2. Are you using the same email on all 27 firewalls, or are they different among the firewalls?
- Are the 27 firewalls configured the same in terms of packages? If using something like pfBlocker or an IDS/IPS package, are the downloaded and active IP lists and rules exactly the same across the 27 firewalls?
- Make sure the time is correct on all the firewalls. A bad time/date on a firewall could cause issues with validating certs.
And what is the exact error message you are getting back in return? If you can see the admin side of the Office365 account, have a look in there to see if the mail connection attempt is being rejected for some reason.
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Hello!
Check your "SMTP" server address...
"smpt.office365.com" ?
John
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Did I just heard that head slapping ?
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You heard a slap against my forehead as well. I completely missed that typo when I reviewed the OP's screen capture the first time.
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@bmeeks All firewalls have same configuration for SMTP but only 4 receive that particular error as shown in my screenshot. I have correct time on firewalls.
I am kind of new to Office365, I looked around in admin center in message center, mail flow and alerts but didn't find anything unusual and no trace of emails from those 4 firewalls. Where do I have to look specifically?
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@pfrickroll said in SMTP Email notifications fail in 4 out of 27 pfSenses:
@bmeeks All firewalls have same configuration for SMTP but only 4 receive that particular error as shown in my screenshot. I have correct time on firewalls.
I am kind of new to Office365, I looked around in admin center in message center, mail flow and alerts but didn't find anything unusual and no trace of emails from those 4 firewalls. Where do I have to look specifically?
Did you see the other replies in this thread? I failed to notice that you have misspelled the email server name. You typed "smpt" instead of "smtp" in the email host. Fix that and see if it then works.
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@pfrickroll said in SMTP Email notifications fail in 4 out of 27 pfSenses:
Where do I have to look specifically?
No your never going to connect there.. Because its not smpt is its SMTP..
You have the wrong address..
Which is why its DOH!!
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Like @johnpoz is saying, the error is on your pfSense firewalls (likely all 4 of them that are not working). Notice in your screen shot you posted in your original message that you have the Email Server name spelled wrong. You have "smpt.office365.com" and it should instead read "smtp.office365.com". You have the "t" and "p" backwards in the name.
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I blame it on MS, they should clearly allow for both smtp and smpt ;) to account for their userbase ;) hehehehe
Are not fqdn like nukes - you should just have to be close is all ;)
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Oh my goodness, my eyes. Such a dumb mistake
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ie the whole DOH joke ;)
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@johnpoz I think forums needs emoji reactions :)
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@pfrickroll said in SMTP Email notifications fail in 4 out of 27 pfSenses:
Oh my goodness, my eyes. Such a dumb mistake
Don't feel too bad. I didn't notice the typo either when I replied initially.
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Serbus even wrote it out for me, i read it like "doh" i know. Tell me something else, i feed dumb
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We should submit a bug request to MS about it ;)
they should prob register smpt.office356.com etc.. and all the other possible typo scenarios ;) hehehe
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@johnpoz said in SMTP Email notifications fail in 4 out of 27 pfSenses:
prob register smpt.office356.com
"However, what if one of these bits got automatically flipped due to a solar flare, cosmic rays, or a hardware error? That is one of the 0's becomes a 1 and vice versa.
...
as soon as Remy squatted the aforementioned domains and setup sinkholes to record any traffic, the researcher noticed an uptick in legitimate traffic coming his way.In addition to the traffic destined to windows.com, the researcher was also able to captured UDP traffic destined for Microsoft's time server, time.windows.com, and TCP traffic meant to reach Microsoft's services such as Windows Push Notification Services (WNS) and SkyDrive (former name of OneDrive)."
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Yeah had seen the bitflipping and ntp article - somewhat relatable sure to such typo domains ;)
