SMTP Not working 2

[pontim]

Hi, i´m trying to set up SMTP alerts on Ip office Server edition with a gmail account. I'm using smtp.gmail.com on port 465 with authentication enabled and the credentials are properly loaded. When i initiate test alarms smtp service wakes up, but after establishing connection it closes.

********** SysMonitor v11.1.0.2.0 build 14 [connected to ------------- (explh2981 (Server Edition(E)))] **********
2021-09-13T10:20:29 409124046mS SMTP: SMTPServer woken up... Session 00000000 Client 00000000 State 1 Q Size 10 current_message 00000000
2021-09-13T10:20:29 409124046mS SMTP: SMTPServer has resolved FQDN [smtp.gmail.com] to IP address [172.217.192.108].
2021-09-13T10:20:29 409124047mS SMTP: Initialising communications to SMTP Server [IP Address = 172.217.192.108, port 465)
2021-09-13T10:20:29 409124047mS SMTP: EMail list is now 10 records long
2021-09-13T10:20:29 409124047mS SMTP: SMTPServer Connecting... Session f183cae4 Client f4f0e8c8 tls 0
2021-09-13T10:20:29 409124047mS SMTP: EMail list is now 10 records long
2021-09-13T10:20:29 409124047mS SMTP: SMTPServer: conn. wating for server .. 2 on state 3
2021-09-13T10:20:29 409124047mS SMTP: SMTPServer snoozing...
2021-09-13T10:20:29 409124070mS SMTP: Established communications with SMTP server

********** SysMonitor v11.1.0.2.0 build 14 [connected to ------------- (explh2981 (Server Edition(E)))] **********
2021-09-13T10:20:40 409134127mS SMTP: We have been disconnected from the SMTP server (EndOfData request)
2021-09-13T10:20:40 409134128mS SMTP: SMTPSender ~SMTPTCPSession... Session f183cae4 Client 00000000
2021-09-13T10:20:40 409134128mS SMTP: SMTPServer Connection Closed... Session f183cae4 Client 00000000
2021-09-13T10:20:40 409134128mS SMTP: SMTPServer Snoozing for 5 minutes...

Testin with openssl on port 465 I get a 220 response wich indicates a successfull connection as far as I know.

Any thoughts?

Thanks!

 

[Nortel4Ever]

Have you got Less Secure Apps setup in your Gmail account?
Try Port 587

I have that and it works great.

 

[critchey]

You need to have StartTLS checked under SMTP and use port 587 like Nortel4Ever stated and check the gmail account less secure apps has to be enabled. If a single email fails you need to reboot the system it will simply queue messages after one fails till rebooted (never found a way for it to try again other then rebooting).

The truth is just an excuse for lack of imagination.

 

[derfloh]

Seems that Gmail changed something that IPO dient work decent anymore

IP Office remote service
IP Office certificate check
CLI based call blocking
SCN fallback over PSTN

 

[pontim]

Thanks a LOT! that was it the port and STARTTLS. I had to create a password for apps that dont support double authentication.

That did it!
Thanks again!

 

[Nortel4Ever]

Good! Then throw critchey and me a little pink I think.

 

[pontim]

Sir yes sir!

 

[critchey]

Glad you got it working and thanks for the pink appreciate it.

The truth is just an excuse for lack of imagination.

 

[Nortel4Ever]

Thanks for the pink I appreciate it too.

 

[pontim]

Hi! It's me again.. im having an issue applying the same config in the Primary Server. I get the foloowing response:

2021-09-29T11:50:33 485282632mS PACKET: ev=38404830 v=Sending data to xxx.xxx.xxx.xxx on port 587 p1=0 p2=0
0000 45 48 4c 4f 20 31 37 32 2e 31 36 2e 31 30 2e 31 EHLO xxx.xxx.xxx.xxx
0010 30 0d 0a 0..
2021-09-29T11:50:33 485282755mS SMTP: Processing response for connected state
2021-09-29T11:50:33 485282755mS SMTP: Read response
2021-09-29T11:50:33 485282755mS SMTP: Received expected response of 250
2021-09-29T11:50:33 485282755mS PACKET: ev=38404830 v=Sending data to 172.217.192.109 on port 587 p1=0 p2=0
0000 53 54 41 52 54 54 4c 53 0d 0a STARTTLS..
2021-09-29T11:50:33 485282877mS SMTP: Read response
2021-09-29T11:50:33 485282877mS SMTP: Received expected response of 220
2021-09-29T11:50:33 485282877mS SMTP: SMTPServer Connected...
2021-09-29T11:50:33 485282877mS PACKET: ev=38404830 v=Sending data to 172.217.192.109 on port 587 p1=0 p2=0
0000 45 48 4c 4f 20 31 37 32 2e 31 36 2e 31 30 2e 31 EHLO 172.16.10.1
0010 30 0d 0a 0..
2021-09-29T11:50:33 485282903mS ERR: TLS:Certificate with invalid key usage Src=xxx.xxx.xxx.xxx:10509 Dst=172.217.192.109:587
2021-09-29T11:50:33 485282903mS SMTP: SMTPSender ClientDestroyed... Client f23b7318
2021-09-29T11:50:33 485282903mS SMTP: SMTPSender ~SMTPTCPSession... Session f489ec08 Client 00000000
2021-09-29T11:50:33 485282903mS SMTP: SMTPServer Connection Closed... Session f489ec08 Client 00000000
2021-09-29T11:50:33 485282903mS SMTP: SMTPServer Snoozing for 5 minutes...


I created another app password in gmail... and up to this point there seems to be connection with the smtp server.

Any ideas?

 

[critchey]

It is odd you are getting a TLS certificate error because you are using port 587 which should be StartTLS not TLS. In manager, under SMTP, you have StartTLS checked?

The truth is just an excuse for lack of imagination.

 

[pontim]

Yes, i have it checked. Everything is configured the same way as the expansion wich was the first device i got working thanks to your comments. The only difference is the password of course wich was created for the server in particular.

 

[critchey]

When you say the server has a different password I assuming you mean the password to log into the IPO is different for each box? If so that shouldn't make a difference.

The truth is just an excuse for lack of imagination.

 

[pontim]

I mean the password for the gmail account assigned to the server for the smtp functionality. I created a specific app password as I did for the expansion.

 

[critchey]

I have never created a specific app password. Simply turning on allow less secure apps and using the login credentials for the account has always worked for me.

The truth is just an excuse for lack of imagination.

 

[Nortel4Ever]

In my experience as soon as you enable Less Secure Apps, you are automatically presented with a specific password. You still use your Google user name, but use the Less Secure Apps password that you were assigned when you enabled that feature.

 

[critchey]

I have never had to set a less secure apps password either or been given one.

The truth is just an excuse for lack of imagination.

 

[pontim]

Regardless of that i don´t think it has to do with the authentication instance of the whole process.. because i get a connection to the smtp server but get rejected after it sends the data for the mail as seen here:
2021-09-29T11:50:33 485282877mS PACKET: ev=38404830 v=Sending data to 172.217.192.109 on port 587 p1=0 p2=0
0000 45 48 4c 4f 20 31 37 32 2e 31 36 2e 31 30 2e 31 EHLO 172.16.10.1
0010 30 0d 0a 0..
2021-09-29T11:50:33 485282903mS ERR: TLS:Certificate with invalid key usage Src=xxx.xxx.xxx.xxx:10509 Dst=172.217.192.109:587