PP gives me an error when sending multiple emails from Outlook.com account

[killme]

I create 3 test emails in PP using my Outlook.com MSN account. I send them to my Gmail account. I click Send Later for all of them. During the next scheduled email check PP will send 1 or 2 and then give me an error which is pasted below. During the next scheduled email check PP will send another 1 or 2 of them. It's like I can only send 2 email at a time or something. If I click "Send" instead of "Send Later" I don't ever seem to get this error. I'd like to find out more about what's going on so I can report it to Outlook.com since it seems like something on their end.

Code: Select all

--- Version ---
OS: Windows 8.1 (x64) 
POP Peeper: 4.2.0.2001
Webmail: 4.1.0.0
SSL: 1.0.2.6
IMAP: 4.2.0.2001
SendMail: 4.2.0.2001
Profile Picture: 4.2.0.2001
AntiJunk: 4.2.0.2001
Spell Checker: 4.2.0.2001
Web of Trust: 4.2.0.2001

--- Web Test ---
Result: 200
Error: 
Time: 10:14:15 - 10:14:15 (0 s) (-0400)
Data: Mon, 30 May 2016 07:14:17 -0700

--- Error ---
msn.account [0: POP3] ['pop3.live.com' (995) SSL: 1] [Smtp: 'smtp.live.com' (25) SSL: 2]
  Send Mail: Error verifying 'From'
Server Returned: 5.3.3 Unrecognized command
500 5.3.3 Unrecognized command (#500)

[mjs]

For the record until Jeff can get by the forum I tried the same tests and do not get the same problem with POP Peeper: 4.2.0.2001 (same version as yours) on Windows 7.

I tested for this same thing sending 4 (for extra measure) delayed messages and since I noticed you have different incoming/outgoing Servers I tried both my settings and your settings (see below). I'm assuming you of course have POP enabled in your Outlook.com ("Options" > "Connect devices and apps with POP").

I tried the same thing you tested with my server settings for POP3 first.
Incoming: pop-mail.outlook.com - using "SSL/TLS".
Outgoing: smtp-mail.outlook.com - using "STARTTLS". (server requires authentication)
Sent 4 delayed messages (send later) to a Gmail account and all worked.

So then I tried the same thing you tested again using your server setting for POP3 instead.
Incoming: pop3.live.com - using "SSL/TLS".
Outgoing: smtp.live.com - using "STARTTLS". (server requires authentication)
Sent 4 delayed messages again to a Gmail account and all worked again.

On a side note, just curious - do you need to us port 25 for "Send Mail" setting?

[killme]

I don't need to use port 25, but when I created the account in PP I used this page as a reference.

Just now, I changed the settings to match what you have and which also matches this page. After sending 4 delayed test emails I didn't get any errors this time.

[mjs]

I don't need to use port 25, but when I created the account in PP I used this page as a reference.

Glad to hear it's working now.

FYI, here is some info on the subject; What is an SMTP port.

[killme]

I spoke too soon. I just got the error again.

I am getting the error when I use the AntiJunk feature to report an email as spam. I send one email to Spamcop and another email to US FTC. In the AntiJunk Settings I use my Outlook.com account for "Email from" for both Spamcop and US FTC. When I send the emails all at once I get the error, but if I do it one by one it works just fine.

[mjs]

I spoke too soon. I just got the error again.

I am getting the error when I use the AntiJunk feature to report an email as spam. I send one email to Spamcop and another email to US FTC. In the AntiJunk Settings I use my Outlook.com account for "Email from" for both Spamcop and US FTC. When I send the emails all at once I get the error, but if I do it one by one it works just fine.

If I understand you correctly batching send messages, that is using "Send Later" to send legit messages works now with the settings you now have. But if you use "Send Later" to send SPAM messages to the SPAM Reporting Services ("send the emails all at once") you still get an error, is this what you are saying? If this is correct is it exactly the same error as before and if not then please post the error the next time it occurs.

I've tested using "Send Later" for SPAM and I still have no problem using a "Send Later" for all three SPAM Services (registered with SpamCop to do test).

I've even changed the sending account to an Outlook.com account ("Email from") so that I am doing exactly what you are doing and it still works for me.

If you are doing anything different or getting different results than what I've described above then please elaborate on what it is exactly that you are doing and/or the result details.

Thanks

[Jeff]

killme -- do you think that the problem has always been with the spam-reporting, or do you think you had regular messages causing the problem before you changed the server settings? That is, if you're pretty confident that it's related to spam-reporting, we can focus more on that. **

One thought I had is that maybe outlook.com is detecting your email as spam itself and trying to block it, especially since you're sending the exact same spam via 2 separate emails. However, the error that you're getting really doesn't support that theory -- "error verifying from" would typically occur before PP has even sent the body of the message; and the "unrecognized command" is even stranger.

I think we'll need to get a log of the specifics so that we have a better idea of what's going on. I take it that you're able to duplicate this issue fairly often? Email me (support at esumsoft dot com) so that we can get that.


** Re-reading your original message sounds like it was *not* related to spam-reporting. My original thought was that there may be something wrong on Hotmail's end, as the common errors have been creeping into their IMAP servers again, so that's certainly still a possibility.

[killme]

We traced the problem back to the series of spam messages I report. Each one of the spam messages contains a line with just ".", which tells the SMTP server no more data for the current message is being uploaded and to queue the message for sending. PP sends it's own "." when it's sending the queued emails so two "." were being sent and PP wasn't expecting this. Jeff sent me a new Sendmail.dll which fixed the problem.

I don't know why the test messages I sent experienced the same problem, but sending test messages didn't always trigger the error. The spam reports I was sending would always trigger the error. I'm happy that it got fixed though.

Dan