Frequently Asked Questions

How can I walk through the PYTHEAS MailGate Configuration Wizard again

This can be useful when you want to make major configuration modifications, such as activate outgoing mail, or move to another messaging server. The wizard will not break your existing configuration, it will only modify options which you ask it to modify. Proceed as follows:

• In v. 3.x: Use the button on the About page of the PYTHEAS MailGate Control Panel.
• In v. 2.x: Stop the Pytheas.MailGate service, if you installed the program as a Windows NT/200x service. Then start the PYTHEAS MailGate Communication Task from the Start menu. Go to the Configuration tab, and click on the Configuration Wizard button. Once you are done with the wizard, and if you installed the program as a Windows NT/200x service, exit the Communicaion Task. Then restart the Pytheas.MailGate service.

How can I configure when Session Log messages are sent

How to avoid them completely

• Uncheck the box Send session log message to this Recipient on the Recipient property page. Probably, this box had initially been checked by the Configuration Wizard.

How to receive them

• Check the box Send session log message to this Recipient on a Recipient property page of your choice.
• To receive Session Log messages only in case of a critical situation, check the box Send session log message only if error occurred on the Service options / Logging page. This way you will get session log messages only when it may be worth reading them.
• You may also want to set the Error count threshold... to a value of 2. With this setting, a Session log will not be sent every time a POP3 connection fails; the failure must occur in two subsequent sessions to trigger sending of a Session Log.

Better readability of Session Log messages

• You can make Session Logs more convenient to read if you tell Outlook not to remove line breaks which it may consider useless. To configure Microsoft Outlook this way: go to Options, Mail, Message Format section, uncheck the box Remove superfluous line breaks in raw text messages.

Less important POP3 accounts

• If you have less important POP3 accounts in your configuration, and you do not want a session log message if the connection fails, you may add the word NoWarning to comment-field of these POP3 accounts (supported since v. 2.74).

Write Session Logs to a file

The contents of Session Log messages can be written to a file.

To enable this feature in v.3.x: find the corresponding checkbox on the Service options / Logging page.
To enable this feature in v.2.x: in PMailGat.INI, [Options], configure the Logmsg to disk parameter with a value of 1.

From v. 2.75c, these files are created in the ProgramData\Pytheas\PytheasMailgate\Log (i.e. in the Log subfolder of the folder where PMailGat.ini is located).
Note: up to v. 2.75a, such files are created in the folder where PMailGat.exe is located.

From v. 3.22, such files are systematically written to disk, when an error occurs, even if not requested elsewhere. They will be deleted after 30 days.

How can I transfer an existing installation to a new machine

... and preserve the existing configuration data. We suggest the following steps:

Please note: To be able to see the ProgramData folder in Windows Explorer, we recommend to make hidden files and folders visible. Or just type this name in the address bar of the Windows File Explorer.

• Be sure to have your license key file (pytheas.ini) at hand.
• On the old machine, stop the Pytheas.Mailgate service (or the PYTHEAS MailGate Communication Task).
• On the new machine, install the latest version of the product (we recommend to use the "Upgrade"-Download of the product, not the Evaluation version). Do not  start PYTHEAS MailGate at the end of the setup process. If it does, stop it.
• The next step depends on where your PMailGat.INI file is located on your old machine:
  • If it is located in the \Program_files_(x86)\PytheasMailgate folder:
    Copy the contents of this folder (including all its subfolders) from the old machine to the
    C:\ProgramData\Pytheas\PytheasMailgate
    folder on the new machine. Then, in this folder on the new machine, delete any files with the extensions .exe, .cmd, .dll, .manifest, .tlb, .chm, .hlp, .cnt, .gid.
  • If it is located in the C:\ProgramData\Pytheas\PytheasMailgate folder:
    Copy the contents of this folder (including all its subfolders) from the old machine to the
    C:\ProgramData\Pytheas\PytheasMailgate
    folder on the new machine.
• If they are present, copy  the \Program_Files\PytheasMailgate\SA.CMD , DOS2UNIX.EXE and UNIX2DOS.EXE files from the old machine to the \Program_Files_(x86)\PytheasMailgate folder on the new machine.
• Start the the PYTHEAS MailGate Control Panel. Go to the About tab and activate your license key.
• Go to the About-page to start the Configuration Wizard, and carefully walk through the wizard. Pay special attention to any IP addresses (they are likely to be different on the new machine) and mail server settings (your mail server may be new, too). After the last step, click Apply (if you changed anything) and close the wizard.
• Walk through the PYTHEAS MailGate Control Panel and have a look at the various settings. Pay special attention to any IP addresses.
• On the Dashboard page, you will find the buttons to install and start the Pytheas.Mailgate service.
• If you cannot see your configuration data, please check that you do not have a file named PMailGat.INI in the \Program files_(x86)\PytheasMailgate folder. If you do, please remove it. Then walk through the Configuration Wizard and Control Panel again.

How can I handle many users and mailboxes efficiently?

Initially, PYTHEAS MailGate keeps all its configuration data in an INI file. If you handle email for many mailboxes, the size of this file can approach the size limit imposed on such files by the operating system (this limit may be as low as 64 kB). In such a case we recommend to keep POP3 account and Recipient configuration data in separate files. These files being tab-separated text files, this file can be edited by using your preferred spreadsheet program. Anyway, you can also continue using the Configuration Program as usual.

The procedure and the structure of the new files are discussed in the online help; look for the topics How to keep the list of POP3 Accounts in a separate file and How to keep the list of Recipients in a separate file. How to proceed:

• Make a backup copy of PMailGat.INI.
• In PMailGat.INI, [Options] section, modify one or both of the existing lines Keep accounts in file (for the POP3 account data), or  Keep Recipients in file (for the Recipients data), by adding a file name of your choice, without any path information. For example:
  Keep accounts in file=PmgAccountlist.txt
  If you modify both lines, be sure to use different filenames!
• Restart PYTHEAS MailGate Control Panel (Configuration Program). Initially, the PmgAccountlist.txt file (according to our example) doesn't exist, and the configuration data we be read from PMailGat.INI as before. But when you save your configuration data (make some dummy modification in one of the POP3 account or Recipient configuration), it will be saved to the new file PmgAccountlist.txt, and from this point it will also be read from this file.
• Then you can confirm that the configuration data went into the separate files. These are created in the same folder as PMailGat.INI. You can check the location of this file on the About tab of the Control Panel (Configuration Program).

The following points may be of interest:

• By default, passwords are encrypted, which makes modifying them with a spreadsheet program impossible. You have two choices to get around this problem: only touch the passwords with the Control Panel (Configuration Program), or instruct PYTHEAS MailGate not to encrypt the passwords. You can achieve this by setting the POP3 Password not encrypted parameter to a value of 1 (add this parameter to the [Options] section in PMailGat.INI). However, please note that you will have to retype every POP3 account password after changing the value for this parameter. You can also obtain a software component which implements the password encryption used here.
• To trigger an update of the POP3 accounts or Recipients configuration data inside the Pytheas.Mailgate service after a modification with some spreadsheet program, please start the Control Panel (Configuration Program) with the /touch command line switch.

Running PYTHEAS MailGate as Windows service

In v. 3.x:

• The Configuration Wizard takes care of this.
• On the Dashboard page of the Control Panel, you can install, monitor, start, stop and uninstall the service.

In v. 2.x:

• Go to the Configuration tab of the PYTHEAS MailGate Communication Task, and click the corresponding button.
• Be sure to stop the Communication Task before starting the Pytheas.Mailgate service using the Windows services manager (services.msc).

How to back up the PYTHEAS MailGate configuration files

• You can find out which folder contains the configuration files on the About page of the PYTHEAS MailGate Control Panel (Configuration Program).
  If it is...
  • ProgramData\Pytheas\PytheasMailgate: back up the whole folder including its subfolders.
  • Program_files_(x86)\PytheasMailgate (on x64 systems) or Program_files\PytheasMailgate (on x86 systems): back up any files having an extension which is different of .exe, .cmd, .dll, .manifest, .tlb, .chm, .hlp, .cnt, .gid, .log.

How can I achieve that downloaded messages are not deleted on the POP3 server

• In v. 3.x: Configure the corresponding setting in the POP3 Account properties.
  In v. 2.x: Check the box Don't delete messages forwarded to this Recipient on the Recipient property page for each Recipient.
• In v. 2.x only: If you have a POP3 Account with several Recipients connected to it (such as a "catch-all" POP3 account, which has selective routing criteria), you should also check the box Don't delete non routable messages in the POP3 account properties.
• You may use the Delete mail left on POP3 server after ...days function on the POP3 Account property page to keep your POP3 mailbox clean and the cumulated size of the messages within the allowed limit.

Oversized messages and limitations

How to discover the maximum message size a POP3 mailbox will accept

SMTP/POP3 servers implement a size limit for incoming messages. If you don't know this size limit, here is how to find out.

• Use NSLOOKUP to find the SMTP server which receives mail for your POP3 mailbox. Open a command line window. Replace "yourdomain.com" with the domain suffix of the SMTP address of the POP3 mailbox.
  > NSLOOKUP
> SET TYPE=MX
> yourdomain.com
  You will get the name of the SMTP server (maybe more than one).
  Please note: if you get a local SMTP server doing this, use the SERVER command to connect to an external DNS server (you can often find one in the configuration of your local DNS server, on the Redirectors page).
• Please note: we will now make some changes in the PYTHEAS MailGate Control Panel / Configuration Program. Do not save these !
  Start the PYTHEAS MailGate Control Panel / Configuration Program, it will show the "Your mail server" page,
  If the "on same system..." box is checked: uncheck it.
  In "Hostname or IP address", enter the SMTP server you found with NSLOOKUP.
  Click on "Try connection" and find the line beginning with 250-SIZE which announces the maximum message size (in bytes).
  Then close the PYTHEAS MailGate Control Panel / Configuration Program without saving the configuration.

Now we have to make a decision: do you want to accept messages up to this size on your internal mail server (for ex. Microsoft Exchange) ?

If yes :

• Configure this size limit (in fact, some % more) in the Receive Connector (instructions for Microsoft Exchange 2013 or 2016, 2010 or 2007).

If not :

• In the PYTHEAS MailGate configuration, POP3 Account properties, configure the size limit you are ready to accept ("don't download messages exceeding..."), and configure the Receive Connector accordingly.
• If now an oversized message is found in your POP3 mailbox, this message will not be downloaded, and the Recipient will get a notification from PYTHEAS MailGate. If you configure the Receive Connector accordingly (see links above),  PYTHEAS MailGate (v. 2.72 and later) will read the maximum message size from the Microsoft Exchange response and will not download the message even if you did not complete the previous step (however, you will get a warning in the session log message).
• The message is not deleted in the POP3 mailbox immediately, but it can be later (this is where the "delete mail left on pop3 server after… days" option is significant). You can also delete the message using the "View/Delete messages" function. As long as the message is not deleted, it can still be downloaded if you change the size limit ; however, make sure that your Microsoft Exchange server will be ready to accept it (see above).
• Optionally, PYTHEAS MailGate (v. 2.50 and later) can send a notification back to the sender of the message (cf. the "notify sender..." option). You can customize this system message, "Templates for incoming mail system messages", "Notif. Back to sender for inc.msg over size limit". If this option is greyed out in your configuration, it is because you license key does not activate the "Content-checking Rules" which is necessary to make this working.

Troubleshooting "Unexpected disconnection from POP3 server: The server has closed the connection" situations

This situation needs attention when it happens repeatedly when downloading a particular message. Most of the time we investigated such a situation, the problem was caused by some Antivirus/Antispam program which was hooked into the POP3 connection, and which choked on a particular message.

1. Check with Telnet on the machine where PYTHEAS MailGate is installed

Use this procedure. In step 4, instead of deleting the message (DELE n), type:
RETR n
In a normal situation, this should download the whole message, which willscroll through the command line window.

If Telnet downloads the message without loosing the session, please get in touch with our product support team. Otherwise, please check for an error message at the bottom of the window (beginning with -ERR), which may give us a hint. If there isn't any, continue with step 2.

2. Antivirus/Antispam programs on the machine where PYTHEAS MailGate is installed?

Please stop the Antivirus/Antispam program temporarily and re-check. If the problem persists, please continue with step 3.

3. Antivirus/Antispam function on the Internet firewall?

If you have access to the firewall configuration, please stop the Antivirus/Antispam function temporarily and re-check. If the problem persists, please continue here.

If you do not have access to the firewall configuration, you may first want to investigate further. Redo the Telnet check on other machines, including machines outside your company (going through a different firewall).

4. Make check (1) again, on another machine using the same internet connection

Make check (1) again, this time on another machine in your company. If you have a positive result in this case (i.e. the connection does not break), you should have a close look at the machine running  PYTHEAS MailGate. If the result is negative (i.e. the connection breaks), please continue with check (5).

5. Make check (1) again, on another machine using another internet connection

If you have a positive result in this case (i.e. the connection does not break), you should have a close look at the firewall securing the Internet connection (is there an antivirus/antispam protection running?). If you still get a negative result in this case (which means that so far we did not find any machine for which this check ends with a positive result), you may want to get in touch with the people running the POP3 server.

Messages rejected as spam by Exchange content filtering

If you installed and activated antispam agents on your Microsoft Exchange server, it may happen that the Exchange server rejects certain messages which have been fetched by PYTHEAS MailGate. On the other hand, PYTHEAS MailGate considers message transfer complete only once the message has been accepted by the downstream mail server. So such messages will be retried over and over again.

To solve this problem, either switch off the antispam agents, or tell PYTHEAS MailGate (beginning with the 2.74 version) what the error message looks like when this happens.

The way to do it in v. 3.x: Configure this on the Content-Checking Rules page, Spam detection, Mail server content filter.

The way to do it in v. 2.x: We introduced the following parameters in the configuration file (PMailGat.INI), in the [Rules] section (these parameter names are automatically added):

• Rejected as spam SMTP error code=550 (the parameter gets this value by default, and it should be correct most of the time)
• Rejected as spam SMTP response: by default, the value for this parameter is empty; this disables the function. You should add there something like: "Message rejected as spam by Content Filtering" (this value works fine with Exchange 2013). The value must have a minimum length of 4 symbols, and this must be a character string which appears in the smtp error message. Upper or lowercase is not important. Such a message may appear in session log messages, or in real time in the Remote Control Program.

Stop the PYTHEAS MailGate service, make the adjustments to the configuration file, and restart it. In the Configuration Program, at the bottom of the Content-checking-page, it should now be visible that this function has been activated.

How do I specify allowed attachment file types using the Content Checking Rules

You need to create two Content-Checking Rules:

• a Pass-Through Rule which defines the masks for allowed file extensions (you need to define all different masks in a single Rule):
  - call it (for ex.): Allow these extensions;
  - on its Attachments page, configure the list of masks which define the allowed file extensions (for ex.: *.doc; *.zip; *.gif).
• an Intercept-Rule for any file attachments:
  - call it (for ex.): Deny all;
  - on its Attachments page, enter: * (one single asterisk);
  - be sure that this Rule is lower in the list than the Allow... rule.

You may want to check your arrangement with the Try Content-Checking Rules function.

Using Hidden Message Headers for Message Routing

Some Background

Normally, the To: and Cc: headers are used to route incoming messages. However, in case of messages for which you receive a blind carbon copy (BCC), or a message from a mailing list, the information in these headers cannot directly be used for message routing. No problem if each user has his own POP3 mailbox, but with a catch-all POP3 account, routing of such messages may be problematic.

To achieve correct message routing in such cases,  examine the (hidden) message headers of a message which you received from your POP3 account (in Microsoft Outlook, use the Options dialog while having the message displayed in its window). The goal is to find a message header which preserved the RCPT-TO information used in the SMTP protocol when the message has been delivered to the ISP's POP3 server. Candidates for such headers are Delivered-To, X-Envelope-To, Envelope-To or others. If the value of this header makes it possible to understand to which SMTP address the message has been delivered, you found a useful one. Unfortunately, some SMTP/POP3 servers do not preserve this information.

How to Use the Hidden Message Header

• Configure the name of the hidden message header on the POP3 account property page. Choose among the values in the list, or type in the name of the header you found.
• On the property page for Recipients being connected to the POP3 account, look at the caption text for Keywords and Other SMTP addresses in the Message Routing Criteria frame. It will show you which one of these properties will be used to identify the Recipient in the value of the configured hidden message header.
• If Keywords are used for identification, the value of the hidden message header must pass Address Validation first, just like a SMTP address found in the To or Cc headers of a message. In such a case, Address Validation should have a value like @company.com.
• If Other SMTP Addresses are used for identification, the message routing algorithm searches for the Recipient's SMTP address and the Other SMTP addresses in the value of the hidden message header.
• To tune how the value of the hidden message header is used by the routing algorithm: open the PMailGat.INI file and look for the [Envelope information Header Masks] section.
  Please note: it will appear once you save the new configuration.
  Examples of lines you may find in there:

If you need to change this information, exit the Control Panel/Configuration Program, edit the PMailGat.INI file in notepad, then restart the Pytheas.MailGate service.

The Subject line gets a [Man.Distr] prefix

The objective of this prefix is to help the reader distinguish between messages sent to him, and messages making it into his mailbox because they could not be routed otherwise.

What you should do depends on your configuration:

• Each internal mailbox has its own POP3 account: in this case, you should check the "route all mail..."-checkbox in the Recipients properties (more...).
• Messages from the POP3 account are distributed to several internal mailboxes: if this isn't a typo made by the sender of the message, you should either add a new Recipient with the corresponding  Message Routing Criteria, or modify an existing one (more...).

How to delete a message from a POP3 mailbox using Telnet

Please note: Beginning with version 2.15a, you can use the tool integrated into the Control Panel / Configuration Program to do this (POP3 Account property page).

1. Connect to the POP3 server

If the Telnet client program is not yet installed on your computer (in fact, it is not installed be default since Microsoft Windows Server 2008): you can install it via Control Panel, Programs and Features, Turn Windows features on or off, Features..

Execute TELNET.EXE (command line interface) and type...

• OPEN POP3server 110

After successfully connecting to the POP3 server, it should reply with a welcome message.

2. Get the list of messages on the POP3 server

Type...
USER POP3user
PASS POP3password
LIST

Please note that the password is case sensitive. Please note that you should avoid typos... the backspace key is not functional in this context :-(

3. Identify the message to delete

The LIST command produced a list of messages and their sizes in the POP3 mailbox. To further identify a particular message, you can type:
TOP n 0
where n is the number of one of the messages listed; the trailing 0 is a zero.

4. Delete the message(s)

Type
DELE n
where n is the number of the message to delete.

5. Disconnect

Once you are finished, it is important to correctly disconnect from the POP3 server by typing:
QUIT

How to make a trace of the dialog with a POP3 server

• If you configured PYTHEAS MailGate not to delete messages after downloading them, and you want to obtain the trace for a particular message which has already been downloaded, but still contained in a POP3 mailbox: click on the Clear message Ids button (on the property pages of the POP3 Account), so PYTHEAs MailGate will "forget" about the messages which have already been downloaded. When doing this, it may be a good idea to use the View/delete messages tool (on the property pages for POP3 Accounts) to delete messages which are of no further interest.
• In the PMailGat.INI file, in the [Options] section, set the following parameter:
  POP3 Trace=1
  (modify the parameter value if it already exists; otherwise, add a new line line. You should avoid copy and paste here as this may introduce some other character between POP3 and Trace instead of the required space character.)
• Stop the Pytheas.Mailgate service.
• Before v. 3.20: start the PYTHEAS MailGate Communication Task (PMailGat.exe) from the Windows File Manager (in v. 2.x you can use the Start menu). You should see a line confirming that the trace has been activated.
• After v. 3.20: restart the Pytheas.Mailgate service. In the PYTHEAS MailGate Remote Control, Session page, at the beginning of a download session, you will get a confirmation that writing to the trace file has been activated.
• Go through a download session (click on the button in the toolbar). Wait for the session to complete.
• Stop the PYTHEAS MailGate Communication Task / service.
• In the PMailGat.INI file, reset the parameter:
  POP3 Trace=0
• Restart the Pytheas.Mailgate service.
• You will find the POP3 protocol trace in the PmgPOP3Trace.txt file in the same folder as  PMailGat.INI. You may replace passwords by XXXX (search for >>PASS). If the trace file is too big for email transmission (more than 20Mb), even in compressed form, you can use the following link to transfer you file (in the form, please prefix your company name by PMG): http://support.pytheas.com/srq/pupload.aspx.

How to make a SMTP trace of the dialog with the internal mail server (Microsoft Exchange or Lotus Domino)

• You will get a detailed SMTP trace only with PYTHEAS MailGate v. 2.40 and later.
• If you configured PYTHEAS MailGate not to delete messages after downloading them, and you want to obtain the trace for a particular message which has already been downloaded, but still contained in a POP3 mailbox: click on the Clear message Ids button (on the property pages of the POP3 Account), so PYTHEAs MailGate will "forget" about the messages which have already been downloaded. When doing this, it may be a good idea to use the View/delete messages tool (on the Delete/Cleanup tab of property pages for POP3 Accounts) to delete messages which are of no further interest.
• In the PMailGat.INI file, in the [Options] section, set the following parameter:
  Inbound SMTP Trace=1
  (modify the parameter value if it already exists; otherwise, add a new line line. You should avoid copy and paste here as this may introduce some other character instead of the required space character between the words.)
• Stop the Pytheas.Mailgate service.
• Before v. 3.20: start the PYTHEAS MailGate Communication Task  (PMailGat.exe) from the Windows File Manager (in v. 2.x you can use the Start menu). You should see a line confirming that the trace has been activated.
• After v. 3.20: restart the Pytheas.Mailgate service. In the PYTHEAS MailGate Remote Control, Session page, at the beginning of a download session, you will get a confirmation that writing to the trace file has been activated.
• Go through a download session (click on the button in the toolbar). Wait for the session to complete.
• Stop the PYTHEAS MailGate Communication Task / service.
• In the PMailGat.INI file, reset the parameter:
  Inbound SMTP Trace=0
• Restart the Pytheas.Mailgate service.
• You will find the SMTP protocol trace in the PmgInboundSMTPTrace.txt file in the same folder as  PMailGat.INI.

Troubleshoot outgoing mail handling: messages are not queued in the PYTHEAS MailGate queue of outgoing messages

Start the PYTHEAS Mailgate Remote Control program, and watch the Outbound transfer page. The Remote Control program has trouble connecting to the Pytheas.Mailgate service, confirm that this service is running.

Send a message from a corporate email client program to an Internet email address. When an outgoing messages is accepted in the PYTHEAS Mailgate outgoing mail queue, you get the following lines:

[00:50] Queue [1] ESMTP Connection accepted from: your-mail-server
[00:50] Queue [1] Mail From: <webmaster@pytheas.com> SIZE=3798 (Pmg1F7B.tmp, Priority:  High)
[00:50] Queue [1] Rcpt To: <somebody@somedomain.com>
[00:50] Queue [1] Subject: A sample message
[00:50] Queue [1] Connection closed.

If you get a similar result, messages are in fact accepted in the outgoing mail queue (which means that you don't have the problem). If these messages have problems leaving the queue, you may want to check our article about Relaying denied errors.

If you do not get this result, check the outgoing mail queue of your corporate mail server (the one the client program connects to). You should have the outgoing message waiting there.

• If you do, continue with Check A1.
• Otherwise, check with the destination, if the message has been sent anyway.
  • If it has been, but you want outgoing mail flow through PYTHEAS MailGate, please read about Check C first.
  • If it has not been sent, check that your mail server has been correctly configured to handle outgoing Internet mail.

Check A1: Check with the PYTHEAS MailGate Configuration Program if the Pytheas.MailGate service is listening for outgoing mail

In v. 2.x: On the machine running the Pytheas.Mailgate service, open the PYTHEAS MailGate Configuration Program, go to the Outgoing mail page, and click on the Try to listen for outgoing message now... button. You should get the following response:

*** The port could not be opened for listening.
*** Now trying SMTP connection to port 2500...
220 PYTHEAS MailGate ESMTP server ready
HELO Your_machine_name
250 PYTHEAS.MailGate
QUIT
*** The SMTP connection has been closed

If you get this result, skip to check B. If you don't, go to check A3.

Check A3: Look for error messages when the PYTHEAS MailGate Communication Task starts

Stop the Pytheas.Mailgate service and start the PYTHEAS MailGate Communication Task (PMailGat.exe) from the Windows File Manager (in v. 2.x you can use the Start menu). Wait a couple of seconds. Confirm that you get something similar to the following message on the Session page:

[00:10] Now queuing outbound messages in C:\ProgramData\Pytheas\PytheasMailgate\Outgoing; listening on TCP port 2500.

• If you get this message or a similar one, and the previous check did not perform as expected, proceed as follows:
  • Leave the Communication Task running, do not restart the Pytheas.Mailgate service, and try again (Check A1).
  • If you get better results now, modify the start-up parameters of the Pytheas.Mailgate service to have it start up with a "real" user account (by default, this service runs in the localsystem context). Then terminate the Communication Task, start the Pytheas.Mailgate service, and run Check A1 again.
• If you get an error message at this point, check that there is no other service using the TCP port that PYTHAS Mailgate tries to use. In this case, either stop - or reconfigure - the other service, or switch PYTHEAS MailGate to another TCP port; please note that you will have to configure the new TCP port number in your mail server configuration, too (see below). Then run Check A1 again.

Check B: PYTHEAS MailGate configuration parameters

In the PYTHEAS MailGate configuration program, Outgoing mail page, Listen on IP Addr frame, select: <any available>. If you had another value there, save the modified configuration. Then open the outgoing message queue management program of your corporate mail server to trigger it to resend the waiting message, while observing the the Outbound transfer page in the PYTHEAS Mailgate Remote Control program.

If this solved the problem, you may restrict the IP Address for the listening socket again. Use the IP address of the "smart host" configured for your corporate mail server (see below).

Check C: Check the Corporate Mail Server Configuration

Let's check the IP address and TCP port where your corporate mail server should send outgoing mail.

If you are using Microsoft Exchange Server 2016, Microsoft Exchange 2016, Microsoft Exchange Server 2010 or Microsoft Exchange Server 2007:

Please have a look at this page describing the Microsoft Exchange Server 2013 / 2016 or Microsoft Exchange Server 2010 or Microsoft Exchange Server 2007 configuration.

If you are using Microsoft Exchange 2000 or Microsoft Exchange 2003 server:

Check in the Microsoft Exchange System Manager if you have a SMTP connector in the routing group of your server with a SMTP:* address space, supposed to handle outgoing Internet mail.

• If you do, check on the General page of its property pages, if it configured to send mail to the IP address of the machine running the Pytheas.Mailgate service; this option corresponds to Forward  all mail through this connector to the following smart hosts.
• If you don't, the destination IP address for outgoing mail is configured in the properties of the Default virtual SMTP server in Servers/(Your_Server)/Protocols/SMTP, Delivery page, Advanced button, Smart_host field.

Please note that the IP address needs to be put inside [square brackets].

The outgoing SMTP port is configured in the virtual SMTP server properties, Delivery page, Outgoing connections button. This value should correspond to the value configured in the PYTHEAS MailGate Configuration Program, Outgoing mail page (Listen on IP address / port parameter). Please see our explications in Check A2 about the default value of this parameter.

If you are using Lotus Domino:

Have a look at our configuration guide for Lotus Domino R5/R6 servers, chapter 4 for the name/IP address of the machine to send outgoing mail to, and chapter 2 for the outgoing SMTP port.

If you are using Microsoft Exchange 5.5:

Please check in the Microsoft Exchange Administration Program, on the Connections tab of the property pages of the Internet mail service, that the option Forward all messages to the host is activated, and points to the IP address of the machine running the Pytheas.Mailgate service.

Conclusion

Once we checked that the PYTHEAS Mailgate outgoing mail queue is ready to accept messages, and that your mail server sends outgoing mail to the correct IP address/TCP port, outgoing messages should at least make it into the PYTHEAS MailGate outgoing mail queue. If there are problems to send these messages to the ISP's SMTP relay, please go on reading.

What to check if you get a Relaying denied error (550... SMTP response) when sending outgoing mail

• Frequently, access to the relaying services of a SMTP relay server is bundled with your Internet access. Hence, you should use the SMTP relay server run by your ISP. There is a chance that it will automatically recognize you being allowed to use its services.
• Check if other identification procedures are required (for ex. the AUTH LOGON procedure of the ESMTP protocol); then configure PYTHEAS MailGate accordingly. If you have a firewall, be sure that the required extensions are allowed for outgoing ESMTP connections. You can use the Try connection function on the Outgoing mail tab to check if the login is successful.
• Check that the sender's SMTP address corresponds to the SMTP Address of his POP3 mailbox, and does not belong to some publicly unknown messaging domain.
• Get in touch with the people who run the SMTP relay server and check what are the requirements to use its relaying services.

How can I have more than one user use the same sender's address in outgoing mail?

The sender's address in outgoing email is set by your mail server, and this server generally won't let you set the same SMTP address for two or more users. However, if it handles your outgoing email, you can make it happen with PYTHEAS MailGate.

The trick is to assign SMTP addresses like sales__fk@pytheas.com. to the users being involved. When an outgoing email with such a sender's address is handled, PYTHEAS MailGate removes the two underscores and the characters up to the @-sign (no more than ten characters), thus leaving the sender's address as sales@pytheas.com.

Another interesting feature may be to rewrite the sender's name. In the example above, to achieve that the sender won't show up with his real name, but instead as the Sales Department, you would activate the Rewrite human readable names function on the Outgoing mail page of the Configuration Program, and add the following line:
sales@pytheas.com Sales Department
Please note that only email leaving to the Internet and flowing through PYTHEAS MailGate will be modified in this manner.

Messages which could not be sent are not returned to the sender

This problem is reported with the following error message in the session log:
Queue: *** Error: No notification to: <somesender@yourdomain.com> (The message subject). Sender's address unknown.

Please make sure that the corresponding SMTP address somesender@yourdomain.com either...

• appears as the Recipient's SMTP address, or...
• is listed in a Recipient's Other SMTP addresses property.

Since v. 2.70, you can choose to get a warning with a Session Log message when a message with an "unknown" sender address is accepted in the queue of outgoing messages (check the corresponding checkbox in the Outgoing mail parameters.

How can I get rid of misleading "Not read" confirmations

Outgoing mail handling (v. 2.75c and later) can silently drop messages with a certain message subject prefix. We can use this feature to silently drop "Not read" confirmations.

To configure this option, edit PMailGat.INI and configure the
Silent drop Message_Subject prefix
parameter in the [Outgoing mail] section (this parameter should already be there, with an empty value). "Not read" confirmations are typically prefixed with "not read: ", hence you should configure the following value: Not read:  . Then restart the PYTHEAS MailGate service.
Note: Leading or trailing spaces must be encoded by  . A comma (,) in the subject header prefix must be encoded as ,. Separate multiple values for message subject prefixes by a comma (,). The message subject prefix detection is not case-sensitive and must have at least 4 characters.

Whenever a message is silently dropped, a corresponding message will appear in the Session Log.

Messages with empty Return-Path (MAIL FROM: <>) cannot be send via the SMTP relay

Depending on the configuration of the configuration of the SMTP relay used to send outgoing mail, it may not be possible to send notification messages which typically have an empty Return-Path. In such a situation, you can instruct PYTHEAS MailGate (v. 2.75c and later) to use the value of the FROM header of the message as Return-Path.

To configure this option, edit PMailGat.INI, [Outgoing mail] section, and set the Avoid emtpy MAIL FROM parameter (which should already be there, with a 0 (zero) value) to a value of 1. Then restart the PYTHEAS MailGate service.

Please note: this parameter has no action when outgoing mail is configured to be sent directly.

Make a Trace of an Outgoing SMTP Connection

This may help you understand communication problems between PYTHEAS MailGate and your ISP's SMTP relay server.

• Stop the Pytheas.Mailgate service.
• In the PMailGat.INI configuration file, [Options] section, add the parameter
  Outbound SMTP Trace=2
  (or change its value, it it already exists. You should avoid copy and paste here as this may introduce other characters instead of the required space character.)
• Before v. 3.20: run the PYTHEAS MailGate Communication Task (PMailGat.exe) from the Windows File Manager (in v. 2.x you can use the Start menu). You should get a line confirming the activation of the trace: Outbound SMTP Client trace activated.
• After v. 3.20: restart the Pytheas.Mailgate service. In the PYTHEAS MailGate Remote Control, Session page, you will find the following hint at the beginning of a POP3 download session: SMTP trace for sending outgoing mail activated.
• Now make the problem happen, which you want to examine. The SMTP dialog will be saved in file PmgOutboundSMTPTrace2.txt  (in the same folder as PMailGat.INI)
• Stop the PYTHEAS MailGate Communication Task or service. Reset the value for the parameter mentioned above to 0 (zero).
• Restart the Pytheas.Mailgate service.

Note: For more information on this topic see the online help, chapter Diagnostic of Communication Problems. In the session log, Outbound transfer part, an outgoing connection looks like this:

[10:10] Send: Connecting to smtprelay.isp.com...Login successful...done. (ESMTP, Max size: 21000000, DSN)
[10:10] Send: Mail From: <pmgsupport@pytheas.com> (Pmg5C47.tmp, 7,4 kb, queued: 01/01/2015 10:09:54)
[10:10] Send: Rcpt To: <webmaster@pytheas.com>
[10:10] Send: Subject: This is an outgoing message
[10:10] Send: Message sent (7,4 kb).
[10:10] Send: Outbound connection closed.