Add sender to my exchange out of office mails which are sent via postfix with an empty senderChange Exchange 2010 Out of office to behave like Exchange 2003Exchange 2010 sending old Out of Office messageForward mails based on sender email address and subject directly on Exchange 2007Microsoft Exchange Out of Office reply intervalOut of office broken on Exchange 2007 server wide“Undelivered Mail Returned to Sender” messages from GooglePostfix sent mails are bounced or go to spamPostfix lost connection with “server/host” while receiving the initial server greetingExchange 2010 Out of office reply issue on outlook 2010 Application (Requires user to be an administrator)Postfix - External incoming mails with company domain

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Add sender to my exchange out of office mails which are sent via postfix with an empty sender


Change Exchange 2010 Out of office to behave like Exchange 2003Exchange 2010 sending old Out of Office messageForward mails based on sender email address and subject directly on Exchange 2007Microsoft Exchange Out of Office reply intervalOut of office broken on Exchange 2007 server wide“Undelivered Mail Returned to Sender” messages from GooglePostfix sent mails are bounced or go to spamPostfix lost connection with “server/host” while receiving the initial server greetingExchange 2010 Out of office reply issue on outlook 2010 Application (Requires user to be an administrator)Postfix - External incoming mails with company domain






.everyoneloves__top-leaderboard:empty,.everyoneloves__mid-leaderboard:empty,.everyoneloves__bot-mid-leaderboard:empty height:90px;width:728px;box-sizing:border-box;








0















Out of office mails works internally but externaly the logs says :
- it goes out of Exchange 2010 to go to Postfix (without any sender),
- Postfix sends it out to the sender without any sender
- the destinator bounces it back with the error " status=bounced (host gmail-smtp-in.l.google.com[173.194.76.26] said: 550 Requested action not taken: mailbox unavailable (in reply to MAIL FROM command))"



The RFCs say that out of office mails and other MDNs should be sent with an empty sender. Since Exchange 2010 (or 2007?), that is what it is done.



The problem is that at least Gmail and Hotmail refuse those mails:




status=bounced (host gmail-smtp-in.l.google.com[173.194.76.26] said:
550 Requested action not taken: mailbox unavailable (in reply to MAIL
FROM command))




Internet says that we can't add a sender to those out of office mails in Exchange 2010. There are transport rules but they can't add "From" attribute in header, and email rewriting but... Its like asking me to write a big book in chinese while I just want to have a "cool" chinese character on my arm.



My luck is that my exchange sends mail via a postfix server (Internet -> Postfix -> Exchange) and that we can add sender to mails with postfix.



What I understand is that I can replace things like "*@mydomain.com" to a single static mail address, always the same, that I can choose like "mailer@myStylishDomainName.com" but what I would like to do is add the real sender mail address to the "from". And I would like to do this only if it is a "automatic reply" kind of mail.



How could I add a "from" value to my out of office mails so that gmail and other external mail servers accept my MDNs please?



Update 1 : in addition ton DKIM/DMARC, I saw those roads :



  • fill in external postmaster


You can configure and manage the external postmaster address. The
external postmaster address is used as the sender for system-generated
messages and notifications sent to message senders that exist outside
the Microsoft Exchange Server 2010 organization. An external sender is
any sender that has an e-mail address that contains a domain not
defined in the list of accepted domains for the Exchange 2010
organization.




https://docs.microsoft.com/en-us/previous-versions/office/exchange-server-2010/bb430765(v=exchg.141)



  • change OOF mails format from TNEF to something else: it is possible to avoid TNEF for "normal" mail but I don't know how to force OOF mails to be sent in usual MIME type









share|improve this question
























  • I think external postmaster address could be used for DSN, in my testing OOF would not use this.

    – Shaw
    16 hours ago

















0















Out of office mails works internally but externaly the logs says :
- it goes out of Exchange 2010 to go to Postfix (without any sender),
- Postfix sends it out to the sender without any sender
- the destinator bounces it back with the error " status=bounced (host gmail-smtp-in.l.google.com[173.194.76.26] said: 550 Requested action not taken: mailbox unavailable (in reply to MAIL FROM command))"



The RFCs say that out of office mails and other MDNs should be sent with an empty sender. Since Exchange 2010 (or 2007?), that is what it is done.



The problem is that at least Gmail and Hotmail refuse those mails:




status=bounced (host gmail-smtp-in.l.google.com[173.194.76.26] said:
550 Requested action not taken: mailbox unavailable (in reply to MAIL
FROM command))




Internet says that we can't add a sender to those out of office mails in Exchange 2010. There are transport rules but they can't add "From" attribute in header, and email rewriting but... Its like asking me to write a big book in chinese while I just want to have a "cool" chinese character on my arm.



My luck is that my exchange sends mail via a postfix server (Internet -> Postfix -> Exchange) and that we can add sender to mails with postfix.



What I understand is that I can replace things like "*@mydomain.com" to a single static mail address, always the same, that I can choose like "mailer@myStylishDomainName.com" but what I would like to do is add the real sender mail address to the "from". And I would like to do this only if it is a "automatic reply" kind of mail.



How could I add a "from" value to my out of office mails so that gmail and other external mail servers accept my MDNs please?



Update 1 : in addition ton DKIM/DMARC, I saw those roads :



  • fill in external postmaster


You can configure and manage the external postmaster address. The
external postmaster address is used as the sender for system-generated
messages and notifications sent to message senders that exist outside
the Microsoft Exchange Server 2010 organization. An external sender is
any sender that has an e-mail address that contains a domain not
defined in the list of accepted domains for the Exchange 2010
organization.




https://docs.microsoft.com/en-us/previous-versions/office/exchange-server-2010/bb430765(v=exchg.141)



  • change OOF mails format from TNEF to something else: it is possible to avoid TNEF for "normal" mail but I don't know how to force OOF mails to be sent in usual MIME type









share|improve this question
























  • I think external postmaster address could be used for DSN, in my testing OOF would not use this.

    – Shaw
    16 hours ago













0












0








0








Out of office mails works internally but externaly the logs says :
- it goes out of Exchange 2010 to go to Postfix (without any sender),
- Postfix sends it out to the sender without any sender
- the destinator bounces it back with the error " status=bounced (host gmail-smtp-in.l.google.com[173.194.76.26] said: 550 Requested action not taken: mailbox unavailable (in reply to MAIL FROM command))"



The RFCs say that out of office mails and other MDNs should be sent with an empty sender. Since Exchange 2010 (or 2007?), that is what it is done.



The problem is that at least Gmail and Hotmail refuse those mails:




status=bounced (host gmail-smtp-in.l.google.com[173.194.76.26] said:
550 Requested action not taken: mailbox unavailable (in reply to MAIL
FROM command))




Internet says that we can't add a sender to those out of office mails in Exchange 2010. There are transport rules but they can't add "From" attribute in header, and email rewriting but... Its like asking me to write a big book in chinese while I just want to have a "cool" chinese character on my arm.



My luck is that my exchange sends mail via a postfix server (Internet -> Postfix -> Exchange) and that we can add sender to mails with postfix.



What I understand is that I can replace things like "*@mydomain.com" to a single static mail address, always the same, that I can choose like "mailer@myStylishDomainName.com" but what I would like to do is add the real sender mail address to the "from". And I would like to do this only if it is a "automatic reply" kind of mail.



How could I add a "from" value to my out of office mails so that gmail and other external mail servers accept my MDNs please?



Update 1 : in addition ton DKIM/DMARC, I saw those roads :



  • fill in external postmaster


You can configure and manage the external postmaster address. The
external postmaster address is used as the sender for system-generated
messages and notifications sent to message senders that exist outside
the Microsoft Exchange Server 2010 organization. An external sender is
any sender that has an e-mail address that contains a domain not
defined in the list of accepted domains for the Exchange 2010
organization.




https://docs.microsoft.com/en-us/previous-versions/office/exchange-server-2010/bb430765(v=exchg.141)



  • change OOF mails format from TNEF to something else: it is possible to avoid TNEF for "normal" mail but I don't know how to force OOF mails to be sent in usual MIME type









share|improve this question
















Out of office mails works internally but externaly the logs says :
- it goes out of Exchange 2010 to go to Postfix (without any sender),
- Postfix sends it out to the sender without any sender
- the destinator bounces it back with the error " status=bounced (host gmail-smtp-in.l.google.com[173.194.76.26] said: 550 Requested action not taken: mailbox unavailable (in reply to MAIL FROM command))"



The RFCs say that out of office mails and other MDNs should be sent with an empty sender. Since Exchange 2010 (or 2007?), that is what it is done.



The problem is that at least Gmail and Hotmail refuse those mails:




status=bounced (host gmail-smtp-in.l.google.com[173.194.76.26] said:
550 Requested action not taken: mailbox unavailable (in reply to MAIL
FROM command))




Internet says that we can't add a sender to those out of office mails in Exchange 2010. There are transport rules but they can't add "From" attribute in header, and email rewriting but... Its like asking me to write a big book in chinese while I just want to have a "cool" chinese character on my arm.



My luck is that my exchange sends mail via a postfix server (Internet -> Postfix -> Exchange) and that we can add sender to mails with postfix.



What I understand is that I can replace things like "*@mydomain.com" to a single static mail address, always the same, that I can choose like "mailer@myStylishDomainName.com" but what I would like to do is add the real sender mail address to the "from". And I would like to do this only if it is a "automatic reply" kind of mail.



How could I add a "from" value to my out of office mails so that gmail and other external mail servers accept my MDNs please?



Update 1 : in addition ton DKIM/DMARC, I saw those roads :



  • fill in external postmaster


You can configure and manage the external postmaster address. The
external postmaster address is used as the sender for system-generated
messages and notifications sent to message senders that exist outside
the Microsoft Exchange Server 2010 organization. An external sender is
any sender that has an e-mail address that contains a domain not
defined in the list of accepted domains for the Exchange 2010
organization.




https://docs.microsoft.com/en-us/previous-versions/office/exchange-server-2010/bb430765(v=exchg.141)



  • change OOF mails format from TNEF to something else: it is possible to avoid TNEF for "normal" mail but I don't know how to force OOF mails to be sent in usual MIME type






postfix exchange exchange-2010 email-bounces mdns






share|improve this question















share|improve this question













share|improve this question




share|improve this question








edited 17 hours ago







Philipili

















asked Apr 19 at 12:44









PhilipiliPhilipili

65




65












  • I think external postmaster address could be used for DSN, in my testing OOF would not use this.

    – Shaw
    16 hours ago

















  • I think external postmaster address could be used for DSN, in my testing OOF would not use this.

    – Shaw
    16 hours ago
















I think external postmaster address could be used for DSN, in my testing OOF would not use this.

– Shaw
16 hours ago





I think external postmaster address could be used for DSN, in my testing OOF would not use this.

– Shaw
16 hours ago










1 Answer
1






active

oldest

votes


















0














In my research, it seems related to “Return-Path <>” is empty for MDM notification. It is by default in RFC. I found this related case, maybe you could check the SPF and DKIM policy.






share|improve this answer























  • Thank you for your answer. I already had the SPF but added DKIM and DMARC but it seams to still throw the same error.

    – Philipili
    Apr 23 at 11:17











Your Answer








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1 Answer
1






active

oldest

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active

oldest

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active

oldest

votes









0














In my research, it seems related to “Return-Path <>” is empty for MDM notification. It is by default in RFC. I found this related case, maybe you could check the SPF and DKIM policy.






share|improve this answer























  • Thank you for your answer. I already had the SPF but added DKIM and DMARC but it seams to still throw the same error.

    – Philipili
    Apr 23 at 11:17















0














In my research, it seems related to “Return-Path <>” is empty for MDM notification. It is by default in RFC. I found this related case, maybe you could check the SPF and DKIM policy.






share|improve this answer























  • Thank you for your answer. I already had the SPF but added DKIM and DMARC but it seams to still throw the same error.

    – Philipili
    Apr 23 at 11:17













0












0








0







In my research, it seems related to “Return-Path <>” is empty for MDM notification. It is by default in RFC. I found this related case, maybe you could check the SPF and DKIM policy.






share|improve this answer













In my research, it seems related to “Return-Path <>” is empty for MDM notification. It is by default in RFC. I found this related case, maybe you could check the SPF and DKIM policy.







share|improve this answer












share|improve this answer



share|improve this answer










answered Apr 22 at 8:07









ShawShaw

3094




3094












  • Thank you for your answer. I already had the SPF but added DKIM and DMARC but it seams to still throw the same error.

    – Philipili
    Apr 23 at 11:17

















  • Thank you for your answer. I already had the SPF but added DKIM and DMARC but it seams to still throw the same error.

    – Philipili
    Apr 23 at 11:17
















Thank you for your answer. I already had the SPF but added DKIM and DMARC but it seams to still throw the same error.

– Philipili
Apr 23 at 11:17





Thank you for your answer. I already had the SPF but added DKIM and DMARC but it seams to still throw the same error.

– Philipili
Apr 23 at 11:17

















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