Creating a new mail with To:, Subject:, and simple text in the body, add an attachment like blabla.pdf (with or without choosing File Type: Adobe or Mailer decides) and sending this one results in an

"354 Start mail input; end with <CRLF>.<CRLF>"

and a message with "mail delivery failure". The mail remainsl in the queued folder.
Tried different filenames like "bla bla.pdf", "bla_bla.pdf" and "bla_bla.pdf" - same behavior.
Size of "blabla.pdf" is ~ 2MB.

Tried different pdf-files with different sizes as attachment - same behavior. Seems to be a problem with the .pdf-filetype and not with the files.

Attachment for example like "bla.txt" works fine...

"Filetype.pm" is untouched - no Adobe or pdf-entry is in there...

=================

Version Informations:
Pegasus Mail for Microsoft Windows
Copyright (C) 1992-2022, David Harris, all rights reserved
Electronic mail to support@pmail.gen.nz.

WinPMail version: Version 4.80.1028, Jan 16 2022, build ID 1028
Language resources: Standard UK English resources (EN,0,LL)
Extension Manager version: 1.14
Operating mode: Standalone
User name and ID: Single-user mode, 0
Windows version: 6.2
Windows flag word: 0
WINPMAIL.EXE directory: C:\Program Files (x86)\Internet\PMail\Programs
Home mailbox location: D:\PMAIL\MAIL
New mailbox location: D:\PMAIL\MAIL
TMP environment variable: H:\Temp
TEMP environment variable: H:\Temp
LAN-based SMTP support: N, N, N
NetWare MHS support: N, N, N
Built-in TCP/IP support: Enabled
-WINSOCK version: WinSock 2.0
-WINSOCK path: WSOCK32.DLL
Commandline:
Active -Z options: 32768
PMR variable: (None)
PML variable: (None)
MAI variable: (None)
NB variable: (None)
Autofiltering folders: 3 (3 active, 0 inactive)
Last new mail count: 21
Message size soft limit: 0 bytes
Message size hard limit: 0 bytes
Attachment size soft limit: 0 bytes
Attachment size hard limit: 0 bytes

I have a number of comments.

Regarding the .PDF attachment sending issue, turn on internet session logging and the do a send. The resulting log file may provide a clue into what is happening.
To enable internet session logging go to Tools > Internet options. You will see the logging option at the bottom of the General tab.
The log file will be created in a subdirectory named TCPLogs located in your mailbox directory.

I assume you are running Windows XP or Windows 7. Anything newer should be a problem for Pegasus Mail to run from a subdirectory under C:\Program Files (x86).

Also, H:\Temp is an interesting choice for the location of the system temporary directory. Surprisingly, this does not necessarily reflect the directory being used by Pegasus Mail for its temporary files. That can be specified in PMAIL.INI and is not included in the content of the Info button. My point about this is to make sure that the Pegasus Mail temp directory is accessible.

Windows 6.2 is actually at least Windows 8, the default GetVersion() function of the Windows SDK only returns this value for all versions since Windows 8 unless using a workaround as IER does. IOW: There certainly is an issue with the install path unless all user account control is turned off.

Hi and thanks for reply
OS is Win 10 Pro, user account control is not turned off, active acc is an admin and "H:/temp" is the (sure, moved) window temp directory. You will find there a folder called "Pegasus Mail" with the imageCache and actual entries.
Location in Program Files(x86) remains from the OS upgrade for a long time

New testcycle with session log on / off

• test with session logging off and .pdf as attachment (Filetype is unknown, Encoding is Mailer decides) - failure window and mail entry "Mail Delivery System"... mail ist still in queued folder
• clean up queued mails and exit pegaus
• restart pegasus, creating a new mail with this .pdf attachment (Filetype is unknown, Encoding is Mailer decides), send button pressed, switch session log on and pressed upload - it works with no failure - confused
• switch session log off
• exit pegaus
• restart pegasus, creating a new mail with this .pdf attachment (Filetype is unknown, Encoding is Mailer decides), send button pressed, switch session log off and pressed upload - failure window and mail entry "Mail Delivery System"... mail ist still in queued folder

Hmm... the little network protocol window says... "Connection timeout (no response from host)" in the upper section. Sorry but I took a look at the trace part. But in SMTP settings the timeout parameter is 30 seconds as timeout parameter, in "General" the same and the error window comes ~2 seconds after "POP3: transferring 1%".

next try (with two mails, one without and one with attachment)

• switch session log is off
• restart pegasus, new mail without attachment and send button
• new mail with the .pdf attachment and send button
• upload both messages and works for both messages - are still on provider server and ready for download

last try (again with one mail and attachment)

• switch session log is off
• restart pegasus, new mail with the .pdf attachment, send button and upload - same error at stated above - what the hell...

Seems to be a too specific problem in my installation and I have to life with. A new clean installation with customizing takes a longer time - so no option for me.

POP3 doesn't matter here, and 354 isn't an error (it means "start mail input" or "start with data" ), so without the contents of the SMTP log file there's no way to figure out what actually happens on trying to send the message - you could start with comparing a failing one with a successful one. If posting anything from a log here please make sure it doesn't contain any authentication data (starting with AUTH LOGIN up to something like "Authentication successful" ): Even though they look as being encrypted they are not, it's only a transport encoding being easily decoded by everyone knowing the SMTP rules.

Hi Michael,

as I stated above, it works with "Create Internet session logs.." is ON and doesn't work with OFF.

There is no log file in "..\TCPLogs" with setting "OFF" only the little protocol window.
And with "ON" it works and the log file tells us nothing about an error.

Mysterious...

Tried "Encoding:" no encoding and "File Type" Acrobat... - same problem...

Last try with another provider... (session log is OFF)
Same problem, "SMTP: Sending message 1 of 1... 0%" and the "Network or Protocol Error" window appears with

10:24:03.795: << MAIL FROM:<xxx@xxxx.xxx> SIZE=1057618
10:24:03.872: >> 250 2.1.0 Ok
10:24:03.872: << RCPT TO:<xxx@xxxx.xxx>
10:24:06.890: >> 250 2.1.5 Ok
10:24:06.890: << DATA
10:24:06.902: >> 354 End data with <CR><LF>.<CR><LF>

For the few times I need to send attachments, the workaround with sending a litte mail before this one works for me.
Thanks for you time and replies - no further investigations, please close this thread...

Since it might be of interest for later cases: Did you ever try to send a failing PDF as a zipped file, Sam?

I am as curious as can be about how Pegasus Mail is functioning installed under \Program Files (x86) on Win 10 Pro. Thinking more about this, I guess it would work considering the mailbox location is somewhere else. @idw, would IER update?

It shouldn't take long at all. All settings are stored in the mailbox directory so a new single-user installation, told that the mailbox root directory is at D:\Pmail should just pick up all existing setting and email data. BUT, an unknown to me is whether the current installer will allow you to specify a mailbox location when doing a single-user installation. That would need to be determined.

Since it might be of interest for later cases: Did you ever try to send a failing PDF as a zipped file, Sam?

Hi Michael,
yes,
pdf packed in a zip file, mail created with this attachment, "File Type" is ZIP-Archive, so known by pegasus but the same error occurs when uploading.
Fyi,

• program location is "C:\Program Files (x86)\Internet\PMail\Programs\winpm-32.exe"
• single-user mailbox locates at "D:\Pmail\Mail"
• AND the installation of pmail was manually, means after upgrating the OS to Win10, I copied the "old" program folder to the above mentioned location. The first installation was a very long time ago with Win95. All new versions are installed on top of the old one - i.e. copying from the installation zip-file to the corresponding folder.
• IERenderer (2.7.2.1) is installed and makes updates without problems, means "Update IERenderer" is active (i.e. not grey) after the check at start, click at and download the zip, execute the setup and go.

Hope my english is good enough to explain all .

Sam,
I am still trying to understand how your installation is actually functioning so I have this request. Please look in your "C:\Program Files (x86)\Internet\PMail\Programs\" directory for a file named PMAIL.CFG and let me know if it exists.

Regarding the failure when sending a .pdf attachment, I am baffled. I do not understand why sending a message followed by sending another with the .pdf attached results in a successful send.

Hi Brian,

the mentioned file is still there.

And points to "D:\Pmail\Mail"... and as you see, very old. Created and last changed in 2002 and last moved 2017. The oldest file is "pmsort.exe" from 1993

I have never seen a PMAIL.CFG file contain a path like "D:\Pmail\Mail". In a multi-user installation it will contain a path like "D:\Pmail\Mail~8" or "D:\Pmail\Mail~N", and in a single-user installation it won't exist at all, at least not with the current installer. I wonder if it did in older installers. That would explain why it exists like it does. It sure explains why your installation is working, so thank you for that.

I am sorry that I am still clueless about your .pdf attachment issue.