Emails are now taking about 20 seconds to leave Pegasus Mail on my computer. But if I send emails from an app on my phone, like Yahoo Mail or Gmail, or if I log into Yahoo Mail on my computer and send emails from there, emails are despatched instantly.

In the past year I haven't changed any of the Pegasus settings or other settings on my computer.

I recently changed broadband provider. The download and upload speeds provided by my new broadband provider are much faster than those provided by my previous broadband provider. However, the problem is not the time it takes to upload the contents of an email from Pegasus, but rather the time it takes for an email to BEGIN departing from my computer. It seems to me that there is some delayed "handshaking" or authenticity-checking going on before an email can begin to leave Pegasus Mail on my computer, but these are only guesses.

Can anybody suggest an explanation, or better still a remedy, for this?

What Windows version, Pegasus Mail version, latest IER update installed? Valid printer (driver) selected? Load Windows Internet Services (on Tools > Options > Advanved settings) set to Always? Sending immediately or via Queue Manager? Any difference between HTML (formatted) or plain text messages?

Hello Michael. Thanks very much for your thoughts.

To answer your questions:

I use the latest Pegasus Mail, and in the hope of curing the problem I recently installed the latest Beta version of Pegasus, but that has not caused an improvement.

Yes, the latest IER is installed, I presume - because each time I open Pegasus Mail I see that it checks to see if there is a more recent version of IER to be installed.

Yes, the correct printer driver is automatically selected, and printing an email is not a problem.

Yes, Tools > Options > Advanced settings > Load Windows Internet Services is set to "Always".

I always send emails immediately, and emails only end up in Queue Manager if for some rare reason I have previously disconnected the computer from the Internet.

To see if switching out of Rich text format makes a difference I have just sent a simple text message containing about 20 characters, but the notice in the bottom left of the screen saying "SMTP: Sending message 1 of 1" still took about 20 seconds to change to "1%" and then within an instant the email had gone.

I am using Windows 7 but I don't believe that that has any bearing on this problem because I was using Windows 7 two months ago before this problem developed. Also, when I send an email directly from my Yahoo Mail using my browser inside Windows 7 all emails depart instantly. The problem is occurring only when I send from within Pegasus.

Has Pegasus Mail been restarted? Has the PC been restarted?

Consider creating a new SMTP host record. Research the current settings for the SMTP server to confirm there haven't been any changes. Disable the current one then create a new one to see if that helps.

Finally, internet session logs contain the conversation between Pegasus Mail and the contacted server, with timestamps. Perhaps a log file will provide a clue into where the delay occurs during that process.

• Enable internet session logging at the bottom of the General tab in Internet options.
• The log files are written to a directory named TCPLogs located in the mailbox directory.
• The log files are plain text files.
• Do not post the entire contents of a log file. It will contain your authentication credentials in an easily decryptable form.

@BrianFluet, I have made a TCP log of the sending of an email, which again took about 20 seconds, but am not sure what part of it to post here. I wonder if the following line provides a clue:

20:50:38.997: Connect to 'smtp.tools.sky.com', timeout 25 seconds, flags 16842753.

That is a comment line advising of the contact about to be attempted. I don't the meaning or purpose of the "flags 16842753" portion though. I don't have a flags value in any of mine that I looked at. Anyone out there know the purpose of the flags value?

Below are some lines from one of my SMTP log files. Notice the lines containing the "X"s. Those lines contained my username and password in encrypted, but easily decryped form.
You can safely post the contents of your log as long as you obfuscate or remove that content. For ease, you could just remove the entries between the "AUTH LOGIN" entry and the "authentication succeeded" entry.

21:03:13.375: >> 250 OK<cr><lf>
21:03:13.375: << AUTH LOGIN<cr><lf>
21:03:13.422: >> 334 VXNlcm5hbWU6<cr><lf>
21:03:13.422: << XXXXXXXXXXXXXXXXXXXXXXXX<cr><lf>
21:03:13.469: >> 334 UGFzc3dvcmQ6<cr><lf>
21:03:13.469: << XXXXXXXXXXXXXXXXXXX<cr><lf>
21:03:13.531: >> 235 2.7.0 ... authentication succeeded<cr><lf>

@BrianFluet, I have just noticed that when I send a message from Pegasus the notices in the bottom left corner state: "Sending 1 of 1" and "64 new: 1 queued". I wonder if the "1 queued" offers a clue. I certainly don't what the email to be queued.

Next, I have sent a couple of test emails just now and then gone to the TCP logs as you suggested but there is not an instance of <<AUTH LOGIN>> in the most recent TCP log I have examined. I wonder if this is because I am using IMAP.

Here is a screenshot of today's TCP logs. Should they be like this?

Thanks for your help.

Hmmm, I wonder if there is a message stuck in the queue because it can't be sent. Go to File > Review queued mail. If there is a message there, open it to determine what it is. If it needs to be sent, duplicate it in a new message. Delete the queued message.

I wonder if you only looked at iMAP log files. Outgoing message log files will have the extension .smtp.

Yes.

I had not given a thought to how rapidly IMAP logs can accumulate so consider deleting all old log files, enable logging just before a send, and then disabling it immediately afterwards.

Hello, @BrianFluet.

Thanks for further help.

I can confirm that there is nothing waiting in a queue in Queue Manager before I send emails.

I have just now deleted about 50 log files in the TCP folder, then enabled logging, then sent a brief message (as usual, it took 20 seconds before it departed), and then returning to the TCP folder I have found only one log file, named "TCP-230815-1614-0.smtp", and its contents are as follows. Where there is a long string of Xs in the following, I have replaced characters which I think may be data which ought to be kept private. Can you see anything in the following which explains the delay every time I send an email from Pegasus?

16:14:27.375: --- 15 Aug 2023, 16:14:27.375 ---
16:14:27.455: Connect to 'smtp.tools.sky.com', timeout 25 seconds, flags 16842753.
16:14:28.495: [] Setting SNI hostname to 'smtp.tools.sky.com'
16:14:28.645: [] SSL/TLS session established
16:14:28.655: [] XXXXXXXXXXXXXXXXXXXXXXX, TLSv1.2, Kx=ECDH, Au=RSA, Enc=AESGCM(256), Mac=AEAD<lf>
16:14:28.655: [] Peer's certificate name is '/C=GB/L=Isleworth/O=Sky UK Limited/CN=smtp.tools.sky.com'.
16:14:28.655: >> 220 smtp.mail.yahoo.com ESMTP ready<cr><lf>
16:14:28.665: << EHLO [XXXXXXXXXXXXXXXXXXXXXXX]<cr><lf>
16:14:28.715: >> 250-hermes--production-ir2-XXXXXXXXXXXXXXXXXXXXXXX-4sdwq Hello [XXXXXXXXXXXXXXXXXXXXXXX] [XXXXXXXXXXXXXXXXXXXXXXX])<cr><lf>
16:14:28.715: >> 250-PIPELINING<cr><lf>
16:14:28.715: >> 250-ENHANCEDSTATUSCODES<cr><lf>
16:14:28.725: >> 250-8BITMIME<cr><lf>
16:14:28.725: >> 250-SIZE 41697280<cr><lf>
16:14:28.725: >> 250 AUTH PLAIN LOGIN XOAUTH2 OAUTHBEARER<cr><lf>
16:14:28.735: << AUTH LOGIN<cr><lf>
16:14:28.805: >> 334 XXXXXXXXXXXXXXXXXXXXXXX<cr><lf>
16:14:28.805: << XXXXXXXXXXXXXXXXXXXXXXX<cr><lf>
16:14:28.835: >> 334 XXXXXXXXXXXXXXXXXXXXXXX<cr><lf>
16:14:28.835: << XXXXXXXXXXXXXXXXXXXXXXX==<cr><lf>
16:14:29.035: >> 235 2.7.0 Authentication successful<cr><lf>
16:14:29.035: << MAIL FROM:<XXXXXXXXXXXXXXXXXXXXXXX> SIZE=1270<cr><lf>
16:14:49.115: >> 250 2.1.0 Sender <XXXXXXXXXXXXXXXXXXXXXXX> OK<cr><lf>
16:14:49.125: << RCPT TO:<XXXXXXXXXXXXXXXXXXXXXXX><cr><lf>
16:14:49.165: >> 250 2.1.5 Recipient <XXXXXXXXXXXXXXXXXXXXXXX> OK<cr><lf>
16:14:49.165: << DATA<cr><lf>
16:14:49.215: >> 354 Ok Send data ending with <CRLF>.<CRLF><cr><lf>
16:14:49.215: << From: "XXXXXXXXXXXXXXXXXXXXXXX" <XXXXXXXXXXXXXXXXXXXXXXX><cr><lf>
16:14:49.215: << To: XXXXXXXXXXXXXXXXXXXXXXX<cr><lf>
16:14:49.215: << Date: Tue, 15 Aug 2023 16:14:27 +0100<cr><lf>
16:14:49.225: << MIME-Version: 1.0<cr><lf>
16:14:49.225: << Subject: test<cr><lf>
16:14:49.225: << Reply-to: XXXXXXXXXXXXXXXXXXXXXXX<cr><lf>
16:14:49.225: << Message-ID: XXXXXXXXXXXXXXXXXXXXXXX@XXXXXXXXXXXXXXXXXXXXXXX<cr><lf>
16:14:49.245: << Priority: normal<cr><lf>
16:14:49.245: << X-mailer: Pegasus Mail for Windows (4.81.1154)<cr><lf>
16:14:49.245: << Content-type: Multipart/Alternative; boundary="Alt-Boundary-XXXXXXXXXXXXXXXXXXXXXXX"<cr><lf>
16:14:49.245: << <cr><lf>
16:14:49.245: << --Alt-Boundary-XXXXXXXXXXXXXXXXXXXXXXX<cr><lf>
16:14:49.255: << Content-type: text/plain; charset=US-ASCII<cr><lf>
16:14:49.255: << Content-transfer-encoding: 7BIT<cr><lf>
16:14:49.255: << Content-description: Mail message body<cr><lf>
16:14:49.255: << <cr><lf>
16:14:49.255: << test<cr><lf>
16:14:49.275: << <cr><lf>
16:14:49.285: << --Alt-Boundary-XXXXXXXXXXXXXXXXXXXXXXX<cr><lf>
16:14:49.285: << Content-type: text/html; charset=US-ASCII<cr><lf>
16:14:49.285: << Content-transfer-encoding: 7BIT<cr><lf>
16:14:49.285: << Content-description: Mail message body<cr><lf>
16:14:49.285: << <cr><lf>
16:14:49.295: << <!DOCTYPE html PUBLIC "-//W3C//DTD XHTML 1.0 Transitional//EN"<cr><lf>
16:14:49.295: << "http://www.w3.org/TR/xhtml1/DTD/xhtml1-transitional.dtd"><cr><lf>
16:14:49.295: << <html xmlns="http://www.w3.org/1999/xhtml" xml:lang="en" lang="en"><head><cr><lf>
16:14:49.295: << <title></title><cr><lf>
16:14:49.295: << <meta http-equiv="content-type" content="text/html;charset=utf-8"/><cr><lf>
16:14:49.315: << <meta http-equiv="Content-Style-Type" content="text/css"/><cr><lf>
16:14:49.315: << </head><cr><lf>
16:14:49.315: << <body><cr><lf>
16:14:49.315: << <div align="left" style="min-height: 11pt; "><font face="Arial" size="2"><span dir="ltr" style="font-size:10.0pt; ">test</span></font></div><cr><lf>
16:14:49.315: << </body><cr><lf>
16:14:49.325: << </html><cr><lf>
16:14:49.325: << <cr><lf>
16:14:49.325: << --Alt-Boundary-XXXXXXXXXXXXXXXXXXXXXXX--<cr><lf>
16:14:49.325: << .<cr><lf>
16:14:49.715: >> 250 OK , completed<cr><lf>
16:14:49.735: << QUIT<cr><lf>
16:14:49.775: >> 221 Service Closing transmission<cr><lf>
16:14:49.785: [!] Warning [Benign]: SSL connection improperly closed by remote host.
16:14:49.805: --- Connection closed at 15 Aug 2023, 16:14:49.805. ---
16:14:49.805:

You can see by the timestamps that 20 seconds transpires between these two entries. I don't know what is going on during this time but I assume there is something in the "MAIL FROM:" that is requiring some sort of resolution. Perhaps your authentication email address is different from your internet email address. Check that by looking in Tools > Internet option at the "My internet e-mail address is:" field to see if it is the same as the username in the SMTP host record.

Thanks, @BrianFluet, for showing me where the log is noting that about 20 seconds passes between those two entries.

Your thought that something is going on after or due to the "Mail From" action is a good one.

I have checked that the email address entered at:

Tools > Internet options > General > "My internet e-mail address is:"

is the same as the email address entered at_

Tools > Internet options > Sending (SMTP) > General settings for sending mail (SMTP)" > Edit > Security > "Log into the SMTP server using the following details:".

I have a couple of other email addresses which I very occasionally use in two other Pegasus Mail accounts, so I have just tested sending emails from these to see if emails depart instantly from them, but they too take about 20 seconds, unfortunately.

I am clueless at the moment about what is going on that is causing the delay. It may not be anything that you have any control over. Yahoo prefers OAUTH2 login but still accepts plain login. Yours is plain, as it must be since PMail does not support Yahoo OAUTH2. Perhaps the plain login has something to do with it. I don't know. Your phone app would use OAUTH2. The Yahoo web interface wouldn't need to because you authenticated via login.

If you have any non-Yahoo email accounts you should test to see if there is any delay when sending via their SMTP. If not, then I suspect you are dealing with a Yahoo issue.

Hopefully another forum member who is more knowledgeable about PMail to server communication will post with insights into causes for the delay.

@BrianFluet, thanks.

Because the 20-second "wait" began when I changed to a different Broadband Provider, I think the problem may due to hand-shaking out there in the ether, along a networked route that my previous Broadband Provider did not use.

However, as there is no such wait when I send an email from within Gmail's website or Yahoo's website, I think the issue of authentication could also be involved, as you have suggested.

Perhaps a longer or a somehow different route in the networks in the ether requires a longer processing of authentication.

I have asked the new Broadband Provider why the issue is happening, but it was clear to me from their answer that they have little understanding of what goes on once they have connected me to their system. They DO know how to flick certain switches, such as increasing download and/or upload speeds, but other things are as much a mystery to them as to me.

You mention Gmail's website so I assume you have a Gmail aaccount. Have you tested whether the delay is there when you send a message from Pegasus Mail using Gmail SMTP? Obviously this won't fix the problem but it would isolate whether the issue is with your broadband provider or is specific to Yahoo SMTP.

Well, I'm not sure whether this fits here since I don't quite understand the question (appears to be a non-native speaker and he's talking about a client-server network) starting this thread but it contains some interesting information regarding SMTP handshake delays, mainly these snippets from Bill Cole's first reply:

Any timeout less than 300 seconds conflicts with the reaffirmations in
2008 (RFC5321 http://tools.ietf.org/html/rfc5321#section-4.5.3.2) and
2001 (RFC2821 http://tools.ietf.org/html/rfc2821#section-4.5.3.2) of the
1989 (RFC1123 http://tools.ietf.org/html/rfc1123#page-62) specification
of minimum SMTP timeouts.

IOW: These RFCs are targeted Internet Hosts which are supposed to not expect SMTP servers to respond faster than at most 300 seconds.

And this one:

As Thomas Bleek has noted, you can set an intentional prompt delay in
CGP that applies only to non-client IP addresses. That delay is a very
useful low-cost way to catch "spambot" senders, but anything more than 5 seconds adds little to the bot identification rate while delaying nearly
all mail.

IOW: Someone might deliberately impose delays on messages from your address as a spam protection measure.

Another reason might be a DNS resolution issue, but the author doesn't think it could be the reason in the original poster's case, here's the thread.

PS: Testing with another provider as Brian suggested would most likely answer questions related to these issues.

Hmmmm...., I hadn't thought of that. If the problem can be narrowed down to the broadband provider then looking into testing alternative DNS servers should be considered.

Thanks, @idw and @BrianFluet, for further ideas.

@BrianFluet, how would I go about "testing alternative DNS servers"? I have no idea how to do this. Is it difficult?

It is pretty easy. It is a Windows thing. A web search will produce lots of info on how to do it.

To find alternate DNS server IP addresses I suggest doing a web search for best alternative DNS servers for your country. Then just pick one. At this point you don't need to be concerned about identifying the best, you just need one to test.

Make not of your current DNS IP addresses if any are specified in Windows. It is likely that there aren't which means your PC is using the ones configured in the router. Ones specified in Windows will override the defaults in the router. Deleting them will return your system to using the router defaults.

If an alternative DNS solves the problem then I have a suggestion on how to find the "best" one but it is a little techie and takes some time. I can help you pursue that or you can just pick from your web search results.

Update.

@BrianFluet

Since August I have been away from home and have been able to deal very efficiently with email using the excellent Fairemail app on my Android smartphone. But since arriving back at home 2 days ago I have returned to attending to emails using Pegasus, and, to my astonishment, the problem described above has completely vanished! No longer is there the 20 to 25 second wait before an email departs and Pegasus asks me if I wish to save a copy, during which time no other action was possible within Pegasus! Instead, emails sent from Pegasus are once again winging away instantly.

So what has changed? Well, certainly absolutely nothing has altered at this end, in my home, so I imagine that my internet provider or one of their associated networks has altered or lifted some kind of filter or guard so that emails detected as coming either from Pegasus or Windows 7, or possibly from both, are now allowed to pass through instantly, in just the same way as my emails from apps like Fairemail, Gmail, and Yahoo Mail on my Android devices have always departed instantly.