Cannot connect to SMTP server

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vonitsa
Posts: 53
Joined: Fri Sep 16, 2005 7:27 am

Cannot connect to SMTP server

Post by vonitsa »

Windows 10 pc with latest PP fully updated with a permanent wifi connection.
Here is my weird situation:
One of my email accounts is a business POP3 account and works perfect except when trying to send an email I get an error message that it cannot connect to the SMTP server (netfirms).
When I switch wifi networks (same router) PP is able to send out emails for a short period of time and then gives me again the SMTP server error message. Switching the account to IMAP makes no difference.
PP is allowed through Avast One and Windows firewall and port 587 is open on the router. So any time I have to send out an email (or reply to one) I have to switch networks.
Note that I don't have this problem when I use the same email account through my Android phone (same wifi network).
Hotmail accounts don't have this problem.
Any ideas?
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Jeff
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Re: Cannot connect to SMTP server

Post by Jeff »

That does seem strange. I'm guessing it has less to do with switching wifi network and more to do with Windows resetting something in the wifi that "fixes" it. Here's a few suggestions that I would try:

1) Restart Windows

2) Check if your email provider supports SSL on port 465 instead of STARTTLS (port 587). In PP, edit the account, go to Send Mail and change the top-right dropdown to SSL/TLS.

3) Disable email scanning in your AV. This is usually separate from simply disabling real-time scanning; you'll have to go into Avast settings and disable the email module (temporarily).

If none of that helps:
1) Did this problem start out of the blue or did anything relevant you can think of change?
2) Does it work if you exit/restart PP instead of changing the wifi?
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mjs
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Re: Cannot connect to SMTP server

Post by mjs »

In regards to (step 3 above) disabling the Avast "Mail Shield" (to temporarily test sending messages) -- you might get better results accessing the "Mail Shield" at the Internal "Core Shields" level (Interface) as opposed to disabling "Shields" in general via the Avast tray icon (we have found that, in some cases anyway, disabling the "Email Shield" via the tray icon doesn't always get the results we expect). Note: disabling (unchecking) just the "Scan outbound emails (SMTP)" option (within the "Mail Shield" settings) might suffice, if not however then (temporarily) disabling the Core "Mail Shield" itself (by unchecking the "Enable Mail Shield" option) would be necessary.
Good judgment comes from experience and a lot of that comes from bad judgment. - Will Rogers
vonitsa
Posts: 53
Joined: Fri Sep 16, 2005 7:27 am

Re: Cannot connect to SMTP server

Post by vonitsa »

Same situation after disabling the Avast "Mail Shield".
Restarting Pop Peeper didn't make any difference.
Same email was successfully sent using a web browser but not through Pop Peeper.
Email provider (netfirms) does not support SSL on port 465 so I am using NO SSL on port 587.
I can send emails only if I change networks.
vonitsa
Posts: 53
Joined: Fri Sep 16, 2005 7:27 am

Re: Cannot connect to SMTP server

Post by vonitsa »

More problems now. Two of my Hotmail account gives me an error ( the same) when sending. This time changing networks won't resolve the problem.
Please see picture and log below:
--- Version ---
OS: Windows 10 (x64)
POP Peeper: 5.4.5.0
Webmail: 5.1.0.0
SSL: 1.1.1.19
IMAP: 5.4.5.0
SendMail: 5.4.5.0
Profile Picture: 5.4.5.0
AntiJunk: 5.4.5.0
Spell Checker: 5.4.5.0
Trusted Sites: 5.4.5.0
PPTweaker: 5.4.5.0
Updater: 1.0.0.0

Program folder: C:\Program Files (x86)\POP Peeper\
Ini file: C:\Users\Spiro\AppData\Roaming\POP Peeper\poppeeper.ini
Data folder: C:\Users\Spiro\AppData\Roaming\POP Peeper\

--- Error ---
Spiro [1000: IMAP] ['imap.outlook.com' (993) SSL: 1] [Smtp: 'smtp-mail.outlook.com' (587) SSL: 2] [oauth: 1] [consec: 16]
- Send Mail: Login Error: Auth XOAUTH2
Server Returned: 5.7.3 Authentication unsuccessful [CH0PR03CA0196.namprd03.prod.outlook.com 2023-02-11T15:46:57.881Z 08DB0BFEA0E9EFFA] (#535)
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mjs
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Joined: Sun Jul 17, 2011 2:36 am

Re: Cannot connect to SMTP server

Post by mjs »

This error is due to a current problem with Outlook’s SMTP servers.

Please use the password method instead of Oauth2 -- for details see: Outlook SMTP Oauth2 error.
Good judgment comes from experience and a lot of that comes from bad judgment. - Will Rogers
vonitsa
Posts: 53
Joined: Fri Sep 16, 2005 7:27 am

Re: Cannot connect to SMTP server

Post by vonitsa »

Thank you mjs. Problem with the Hotmail accounts is solved. But the POP3 account still gives me an error.
Very frustrating since this is a business account and cannot reply to customers.
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mjs
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Re: Cannot connect to SMTP server

Post by mjs »

And you had already formerly tried STARTTLS using port 587 (for "Send Mail" settings on the POP3 account) - right?

Has anything you know of changed as of the time the issue started with your POP3 account? (i.e. security software updates or changes that might possibly be contributing to the issue)

Have you tried rebooting the computer?

Please post (in this topic) the specific error you get with the POP3 account (like you did for the Hotmail errors).
Good judgment comes from experience and a lot of that comes from bad judgment. - Will Rogers
vonitsa
Posts: 53
Joined: Fri Sep 16, 2005 7:27 am

Re: Cannot connect to SMTP server

Post by vonitsa »

I rebooted the computer and the router several times. I even updated the wifi adapter driver. No luck.
This is the error it gives me using NO SSL port 587
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And this is the error I get when using STARTTLS port 587
Untitled1.png
Untitled1.png (5.25 KiB) Viewed 932 times
No security software updates or other changes happened that I recall.
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Jeff
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Joined: Sat Sep 08, 2001 9:46 pm

Re: Cannot connect to SMTP server

Post by Jeff »

It's possible that the server does support STARTTLS if it got to that error. Do you have a personal domain? If so, that may explain the error; there's multiple reasons why, but you can try setting an exception for the host (this isn't something I would always recommend, but it's significantly better than not using SSL at all):
1) PP main menu: Tools / PPtweaker
2) Select the "certificates" page on the left
3) In the edit box, add your SMTP host (e.g. smtp.domain.com)
4) Press OK and test sending (make sure that your SMTP account is using STARTTLS and also make sure that it's in a working state)

Now, something that's interesting here -- Your "no ssl" prompt suggests it couldn't connect. But your "starttls" error suggests that it *did* connect -- it has to connect in order to even attempt the TLS socket connection.

My guess is you have some security software (maybe even Windows itself) blocking unencrypted connections on port 587. Have you noticed a pattern? ie. you're able to send one message unencrypted, but the next time it fails?
vonitsa
Posts: 53
Joined: Fri Sep 16, 2005 7:27 am

Re: Cannot connect to SMTP server

Post by vonitsa »

Nothing helps...
I experimented with PP a lot, I even unchecked the SSL verification button hoping to instruct it NOT to check for a verification. I paused Malwarebytes, Avast, Windows Firewall.
Nothing...
The funny thing is that if I wait a few minutes PP sometimes sends the messages meaning that it connects to the server as long as they are not marked as "suspended" in the outbox status.
I am leaning towards it is PP's fault. Do you think re-installing it might help?
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Jeff
Admin / Developer
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Joined: Sat Sep 08, 2001 9:46 pm

Re: Cannot connect to SMTP server

Post by Jeff »

If it was PP's fault, then I would expect exiting/restarting to fix it, and you said that didn't work. If it's intermittent, then that also suggests that the problem is probably on the server's end.

If you have a corrupt program file, then re-installing might help. You can look under Help / About and check the "CRC" for any failures. Regardless, you can try re-installing either way, it won't hurt anything.

The only other thing I can think of to do at this point -- if you're willing to create a (temporary) email account on your server, I can experiment with it and see if I can (a) get TLS to work and (b) see if I have any issues. If so, email me (support at esumsoft dot com).
vonitsa
Posts: 53
Joined: Fri Sep 16, 2005 7:27 am

Re: Cannot connect to SMTP server

Post by vonitsa »

Jeff,
Thank you for all your efforts to help me. Great support.
Please look at my CRC below:
CRC.png
I just re-installed PP. Same situation.
I emailed you with the temporary account info.
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