diff --git a/pkgs/os-specific/linux/nixos-rebuild/nixos-rebuild.8 b/pkgs/os-specific/linux/nixos-rebuild/nixos-rebuild.8
index b0ff5b0a672f..d947361b3bc5 100644
--- a/pkgs/os-specific/linux/nixos-rebuild/nixos-rebuild.8
+++ b/pkgs/os-specific/linux/nixos-rebuild/nixos-rebuild.8
@@ -421,6 +421,14 @@ nixpkgs=./my-nixpkgs
 Additional options to be passed to
 .Ic ssh
 on the command line.
+.Ed
+.
+.It Ev NIXOS_SWITCH_USE_DIRTY_ENV
+Expose the the current environment variables to post activation scripts. Will
+skip usage of
+.Ic systemd-run
+during system activation. Possibly dangerous, specially in remote environments
+(e.g.: via SSH). Will be removed in the future.
 .El
 .
 .
diff --git a/pkgs/os-specific/linux/nixos-rebuild/nixos-rebuild.sh b/pkgs/os-specific/linux/nixos-rebuild/nixos-rebuild.sh
index 2f89642845e2..68e00690652e 100755
--- a/pkgs/os-specific/linux/nixos-rebuild/nixos-rebuild.sh
+++ b/pkgs/os-specific/linux/nixos-rebuild/nixos-rebuild.sh
@@ -653,18 +653,48 @@ fi
 # If we're not just building, then make the new configuration the boot
 # default and/or activate it now.
 if [[ "$action" = switch || "$action" = boot || "$action" = test || "$action" = dry-activate ]]; then
-    if [[ -z "$specialisation" ]]; then
-        cmd="$pathToConfig/bin/switch-to-configuration"
+    # Using systemd-run here to protect against PTY failures/network
+    # disconnections during rebuild.
+    # See: https://github.com/NixOS/nixpkgs/issues/39118
+    cmd=(
+        "systemd-run"
+        "-E" "LOCALE_ARCHIVE" # Will be set to new value early in switch-to-configuration script, but interpreter starts out with old value
+        "--collect"
+        "--no-ask-password"
+        "--pty"
+        "--quiet"
+        "--same-dir"
+        "--service-type=exec"
+        "--unit=nixos-rebuild-switch-to-configuration"
+        "--wait"
+    )
+    # Check if we have a working systemd-run. In chroot environments we may have
+    # a non-working systemd, so we fallback to not using systemd-run.
+    # You may also want to explicitly set NIXOS_SWITCH_USE_DIRTY_ENV environment
+    # variable, since systemd-run runs inside an isolated environment and
+    # this may break some post-switch scripts. However keep in mind that this
+    # may be dangerous in remote access (e.g. SSH).
+    if [[ -n "$NIXOS_SWITCH_USE_DIRTY_ENV" ]]; then
+        log "warning: skipping systemd-run since NIXOS_SWITCH_USE_DIRTY_ENV is set. This environment variable will be ignored in the future"
+        cmd=()
+    elif ! targetHostCmd "${cmd[@]}" true &>/dev/null; then
+        logVerbose "Skipping systemd-run to switch configuration since it is not working in target host."
+        cmd=("env" "-i" "LOCALE_ARCHIVE=$LOCALE_ARCHIVE")
     else
-        cmd="$pathToConfig/specialisation/$specialisation/bin/switch-to-configuration"
+        logVerbose "Using systemd-run to switch configuration."
+    fi
+    if [[ -z "$specialisation" ]]; then
+        cmd+=("$pathToConfig/bin/switch-to-configuration")
+    else
+        cmd+=("$pathToConfig/specialisation/$specialisation/bin/switch-to-configuration")
 
-        if [[ ! -f "$cmd" ]]; then
+        if [[ ! -f "${cmd[-1]}" ]]; then
             log "error: specialisation not found: $specialisation"
             exit 1
         fi
     fi
 
-    if ! targetHostCmd "$cmd" "$action"; then
+    if ! targetHostCmd "${cmd[@]}" "$action"; then
         log "warning: error(s) occurred while switching to the new configuration"
         exit 1
     fi