From 89223af8fefcc5f32a5f79591402e45ce6796d13 Mon Sep 17 00:00:00 2001
From: Ricardo Correia <someplaceguy@wizy.org>
Date: Wed, 18 Feb 2026 22:05:34 +0000
Subject: [PATCH] opensmtpd: fix offline enqueueing

Note: for it to work correctly, it requires `services.opensmtpd.setSendmail` is
set to true.

Fixes #255691

Co-authored-by: Sandro <sandro.jaeckel@gmail.com>
---
 nixos/modules/services/mail/opensmtpd.nix | 21 +++++++++++++++------
 pkgs/by-name/op/opensmtpd/offline.patch   | 20 ++++++++++++++++++++
 pkgs/by-name/op/opensmtpd/package.nix     | 14 ++++++++++++--
 3 files changed, 47 insertions(+), 8 deletions(-)
 create mode 100644 pkgs/by-name/op/opensmtpd/offline.patch

diff --git a/nixos/modules/services/mail/opensmtpd.nix b/nixos/modules/services/mail/opensmtpd.nix
index ba5226351a57..4ec30ce09dae 100644
--- a/nixos/modules/services/mail/opensmtpd.nix
+++ b/nixos/modules/services/mail/opensmtpd.nix
@@ -105,12 +105,21 @@ in
       };
     };
 
-    security.wrappers.smtpctl = {
-      owner = "root";
-      group = "smtpq";
-      setuid = false;
-      setgid = true;
-      source = "${cfg.package}/bin/smtpctl";
+    security.wrappers = {
+      makemap = {
+        owner = "root";
+        group = "smtpq";
+        setuid = false;
+        setgid = true;
+        source = "${cfg.package}/bin/smtpctl";
+      };
+      smtpctl = {
+        owner = "root";
+        group = "smtpq";
+        setuid = false;
+        setgid = true;
+        source = "${cfg.package}/bin/smtpctl";
+      };
     };
 
     services.mail.sendmailSetuidWrapper = lib.mkIf cfg.setSendmail (
diff --git a/pkgs/by-name/op/opensmtpd/offline.patch b/pkgs/by-name/op/opensmtpd/offline.patch
new file mode 100644
index 000000000000..69e36bcc5870
--- /dev/null
+++ b/pkgs/by-name/op/opensmtpd/offline.patch
@@ -0,0 +1,20 @@
+Commit ID: 0527fcb65d6af4271a33dbd425f30d457fc7ab4f
+Change ID: puqrnyuutmspqxqtkkqqrsmsxnyqvomm
+Author   : Ricardo Correia <someplaceguy@wizy.org> (2026-02-18 23:51:00)
+Committer: Ricardo Correia <someplaceguy@wizy.org> (2026-02-19 00:43:47)
+
+    (no description set)
+
+diff --git a/usr.sbin/smtpd/smtpd.c b/usr.sbin/smtpd/smtpd.c
+index 2365b1ee46..b9e40e1417 100644
+--- a/usr.sbin/smtpd/smtpd.c
++++ b/usr.sbin/smtpd/smtpd.c
+@@ -1806,7 +1806,7 @@
+ 		envp[1] = (char *)NULL;
+ 		environ = envp;
+ 
+-		execvp(PATH_SMTPCTL, args.list);
++		execvp(@@PATH_SENDMAIL@@, args.list);
+ 		_exit(1);
+ 	}
+ 
diff --git a/pkgs/by-name/op/opensmtpd/package.nix b/pkgs/by-name/op/opensmtpd/package.nix
index bc1e20cdd177..6bb0ea028df0 100644
--- a/pkgs/by-name/op/opensmtpd/package.nix
+++ b/pkgs/by-name/op/opensmtpd/package.nix
@@ -14,6 +14,7 @@
   pam,
   libxcrypt,
   nixosTests,
+  binPath ? "/run/wrappers/bin",
 }:
 
 stdenv.mkDerivation (finalAttrs: {
@@ -43,11 +44,20 @@ stdenv.mkDerivation (finalAttrs: {
 
   patches = [
     ./proc_path.diff # TODO: upstream to OpenSMTPD, see https://github.com/NixOS/nixpkgs/issues/54045
+    ./offline.patch
   ];
 
   postPatch = ''
-    substituteInPlace mk/smtpctl/Makefile.am --replace "chgrp" "true"
-    substituteInPlace mk/smtpctl/Makefile.am --replace "chmod 2555" "chmod 0555"
+    substituteInPlace mk/smtpctl/Makefile.am \
+      --replace-fail "chgrp" "true" \
+      --replace "chmod 2555" "chmod 0555"
+    substituteInPlace mk/pathnames \
+      --replace-fail "-DPATH_SMTPCTL=\\\"\$(sbindir)" \
+                     "-DPATH_SMTPCTL=\\\"${binPath}" \
+      --replace-fail "-DPATH_MAKEMAP=\\\"\$(sbindir)" \
+                     "-DPATH_MAKEMAP=\\\"${binPath}"
+    substituteInPlace usr.sbin/smtpd/smtpd.c \
+      --replace-fail "@@PATH_SENDMAIL@@" "\"${binPath}/sendmail\""
   '';
 
   configureFlags = [