Solved. I had from previous tries set `regexp` instead of pcre in main.cf 
header checks
 

 
After changing to `pcre` it does what I intended to do.
 
 

 
 
>  
> On Mar 8, 2024 at 9:23,  <Mailinglists35 (mailto:mailinglist...@gmail.com)>  
> wrote:
>  
>  
>  
>  Hi
>  
> I run a postfix 3.5.9 smtp relay for a webserver that sends user signup and 
> forgot password emails. That's the only use case and the server does not 
> receive any other emails and neither generates any locally.
>  
> I'm trying to prevent leaking internal information (hostname  &  IP) in 
> Received header.
>  
> For this, I've setup `smtp_header_checks = regexp:/etc/postfix/header_checks` 
> with the contents:
>  
> /^(Received: from \[127\.0\.0\.1\] \(web\d\w+ 
> \[\d+\.\d+\.\d+\.\d+\]\))((.|\n|\t)*)/m REPLACE Received: from 
> email.domain.tld (email.domain.tld. [1.2.3.4])$2
>  
> I've tested the regex on a regex validation website and it identifies group 1 
> on first line and group 2 the other two lines.  
>
> However I've ran a `postmap` test and it only produces the first line, and 
> skipping the other two lines. With actual incoming emails, replacing does not 
> happen at all.
>  
> The postmap input looks like this:
>  
> echo -e    "Received: from [127.0.0.1] (web1dev [10.11.12.13])\n\tby 
> email.domain.tld (Postfix) with ESMTPS id C9056
>    7E002\n\tfor  <em...@gmail.com>; Fri,    8 Mar 2024 19:20:29 +0200 (EET)" 
> | postmap -q - pcre:/etc/postfix/header_checks
>    Received: from [127.0.0.1] (web1dev [10.11.12.13])     REPLACE Received: 
> from email.domain.tld (email.domain.tld. [1.2.3.4])
>  
> What I am doing wrong?
>  
>  
>  
>  #postconf -n
>  
>  alias_database = hash:/etc/aliases
>  
>    
> alias_maps = hash:/etc/aliases
>  
> bounce_queue_lifetime = 1d
>  
> command_directory = /usr/sbin
>  
> compatibility_level = 2
>  
> daemon_directory = /usr/libexec/postfix
>  
> data_directory = /var/lib/postfix
>  
> debug_peer_level = 2
>  
> debugger_command = PATH=/bin:/usr/bin:/usr/local/bin:/usr/X11R6/bin ddd 
> $daemon_directory/$process_name $process_id  &  sleep 5
>  
> header_checks = regexp:/etc/postfix/header_checks
>  
> html_directory = no
>  
> inet_interfaces = all
>  
> inet_protocols = all
>  
> mail_owner = postfix
>  
> mailq_path = /usr/bin/mailq.postfix
>  
> manpage_directory = /usr/share/man
>  
> maximal_queue_lifetime = 1d
>  
> meta_directory = /etc/postfix
>  
> mydestination = $myhostname, localhost.$mydomain, localhost
>  
> mydomain = $myhostname
>  
> myhostname = email.domain.tld
>  
> mynetworks = $config_directory/mynetworks
>  
> myorigin = $mydomain
>  
> newaliases_path = /usr/bin/newaliases.postfix
>  
> queue_directory = /var/spool/postfix
>  
> readme_directory = /usr/share/doc/postfix/README_FILES
>  
> sample_directory = /usr/share/doc/postfix/samples
>  
> sendmail_path = /usr/sbin/sendmail.postfix
>  
> setgid_group = postdrop
>  
> shlib_directory = /usr/lib64/postfix
>  
> smtp_tls_CAfile = /etc/pki/tls/certs/ca-bundle.crt
>  
> smtp_tls_CApath = /etc/pki/tls/certs
>  
> smtp_tls_security_level = may
>  
> smtpd_tls_cert_file = /etc/pki/tls/certs/postfix.pem
>  
> smtpd_tls_key_file = /etc/pki/tls/private/postfix.key
>  
> smtpd_tls_security_level = may
>  
> transport_maps = hash:/etc/postfix/transport
>  
> unknown_local_recipient_reject_code = 550
>  
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