diff --git a/control/config.txt b/control/config.txt
index e5dd6adb19..8520558550 100644
--- a/control/config.txt
+++ b/control/config.txt
@@ -275,6 +275,7 @@ sitAuto_over_50 0
 sitAuto_idle 1
 sitAuto_look
 sitAuto_look_from_wall
+sitAuto_look_delay
 sitTensionRelax 0
 
 statsAddAuto 0
diff --git a/src/AI.pm b/src/AI.pm
index 5ef42a19cf..ce222483ff 100644
--- a/src/AI.pm
+++ b/src/AI.pm
@@ -758,27 +758,27 @@ sub sit {
 	require Task::SitStand;
 	my $task = new Task::SitStand(actor => $char, mode => 'sit', wait => $timeout{ai_sit_wait}{timeout});
 	AI::queue("sitting", $task);
-	if (defined $config{sitAuto_look} && !$config{sitAuto_look_from_wall}) {
-		Misc::look($config{sitAuto_look});
-	} elsif (defined $config{sitAuto_look} && $config{sitAuto_look_from_wall}) {
-		my $sitAutoLook = $config{sitAuto_look};
-		my $wallRange = $config{sitAuto_look_from_wall};
-		for (my $i=1;$i<=$wallRange;$i++) {
-			if ((!$field->isWalkable($char->{pos}{x},$char->{pos}{y}+$wallRange) && $sitAutoLook == 0)
-			  || (!$field->isWalkable($char->{pos}{x}-$wallRange,$char->{pos}{y}+$wallRange) && $sitAutoLook == 1)
-			  || (!$field->isWalkable($char->{pos}{x}-$wallRange,$char->{pos}{y}) && $sitAutoLook == 2)
-			  || (!$field->isWalkable($char->{pos}{x}-$wallRange,$char->{pos}{y}-$wallRange) && $sitAutoLook == 3)
-			  ) {
-				$sitAutoLook += 4;
-			} elsif ((!$field->isWalkable($char->{pos}{x},$char->{pos}{y}-$wallRange) && $sitAutoLook == 4)
-			  || (!$field->isWalkable($char->{pos}{x}+$wallRange,$char->{pos}{y}-$wallRange) && $sitAutoLook == 5)
-			  || (!$field->isWalkable($char->{pos}{x}+$wallRange,$char->{pos}{y}) && $sitAutoLook == 6)
-			  || (!$field->isWalkable($char->{pos}{x}+$wallRange,$char->{pos}{y}+$wallRange) && $sitAutoLook == 7)
-			  ) {
-				$sitAutoLook -= 4;
+	my $lookDelay = $config{sitAuto_look_delay};
+	$lookDelay = 0 if (!defined $lookDelay || $lookDelay < 0);
+	delete $ai_v{sitAuto_pendingLook};
+	if (defined $config{sitAuto_look}) {
+		my $defaultLook = $config{sitAuto_look};
+		my $lookPlan = { body => $defaultLook, delay => $lookDelay };
+
+		if ($config{sitAuto_look_from_wall}) {
+			my $closestWalls = Misc::getClosestWalls($char->{pos}, $config{sitAuto_look_from_wall});
+			if (@{$closestWalls}) {
+				my $referenceWall = $closestWalls->[int(rand(@{$closestWalls}))];
+				my $oppositeDirectionPos = {
+					x => (2 * $char->{pos}{x}) - $referenceWall->{x},
+					y => (2 * $char->{pos}{y}) - $referenceWall->{y},
+				};
+				my ($bodyDirection, $headDirection) = Misc::getNaturalLookDirections($char->{pos}, $oppositeDirectionPos, $defaultLook);
+				$lookPlan = { body => $bodyDirection, head => $headDirection, delay => $lookDelay };
 			}
 		}
-		Misc::look($sitAutoLook);
+
+		$ai_v{sitAuto_pendingLook} = $lookPlan;
 	}
 }
 
diff --git a/src/AI/CoreLogic.pm b/src/AI/CoreLogic.pm
index edad04a1cc..5adaa5cefb 100644
--- a/src/AI/CoreLogic.pm
+++ b/src/AI/CoreLogic.pm
@@ -414,6 +414,11 @@ sub processClientSuspend {
 }
 
 sub processLook {
+	if ($ai_v{sitAuto_scheduledLook} && time >= $ai_v{sitAuto_scheduledLook}{due}) {
+		my $scheduledLook = delete $ai_v{sitAuto_scheduledLook};
+		Misc::look($scheduledLook->{body}, $scheduledLook->{head});
+	}
+	
 	if (AI::action eq "look" && timeOut($timeout{'ai_look'})) {
 		$timeout{'ai_look'}{'time'} = time;
 		$messageSender->sendLook(AI::args->{'look_body'}, AI::args->{'look_head'});
diff --git a/src/Misc.pm b/src/Misc.pm
index b92c5a3a48..ddc4737b77 100644
--- a/src/Misc.pm
+++ b/src/Misc.pm
@@ -140,6 +140,8 @@ our @EXPORT = (
 	look
 	lookAtPosition
 	lookAtPositionNaturally
+	getNaturalLookDirections
+	getClosestWalls
 	manualMove
 	meetingPosition
 	objectAdded
@@ -2488,14 +2490,14 @@ sub lookAtPosition {
 }
 
 ##
-# lookAtPositionNaturally(from_pos, to_pos, [current_body])
+# getNaturalLookDirections(from_pos, to_pos, [current_body])
 # from_pos: source position hashref (character)
 # to_pos: target position hashref
 # current_body: optional current body direction, defaults to $char->{look}{body}
 #
-# Calculates and executes look change using partial-turn strategy.
+# Calculates look change using partial-turn strategy.
 # Returns: (body, head) where body is 0-7 and head is 0-2.
-sub lookAtPositionNaturally {
+sub getNaturalLookDirections {
 	my ($from_pos, $to_pos, $current_body) = @_;
 	return unless ($from_pos && $to_pos);
 
@@ -2520,10 +2522,65 @@ sub lookAtPositionNaturally {
 		}
 	}
 
+	return ($body, $head);
+}
+
+##
+# lookAtPositionNaturally(from_pos, to_pos, [current_body])
+# from_pos: source position hashref (character)
+# to_pos: target position hashref
+# current_body: optional current body direction, defaults to $char->{look}{body}
+#
+# Calculates and executes look change using partial-turn strategy.
+# Returns: (body, head) where body is 0-7 and head is 0-2.
+sub lookAtPositionNaturally {
+	my ($from_pos, $to_pos, $current_body) = @_;
+	my ($body, $head) = getNaturalLookDirections($from_pos, $to_pos, $current_body);
+	return unless defined $body;
+
 	look($body, $head) if ($body != $char->{look}{body} || $head != $char->{look}{head});
 	return ($body, $head);
 }
 
+##
+# getClosestWalls(from_pos, wall_range, [field_obj])
+# from_pos: source position hashref
+# wall_range: search range around from_pos
+# field_obj: optional field object, defaults to current global field
+#
+# Returns: arrayref with all nearest non-walkable cells found in range.
+sub getClosestWalls {
+	my ($from_pos, $wall_range, $field_obj) = @_;
+	return [] unless ($from_pos && defined $wall_range && $wall_range > 0);
+
+	$field_obj ||= $field;
+	return [] unless $field_obj;
+
+	my $closest_distance;
+	my @closest_walls;
+	for (my $dx = -$wall_range; $dx <= $wall_range; $dx++) {
+		for (my $dy = -$wall_range; $dy <= $wall_range; $dy++) {
+			next if $dx == 0 && $dy == 0;
+
+			my $candidate = {
+				x => $from_pos->{x} + $dx,
+				y => $from_pos->{y} + $dy,
+			};
+			next if $field_obj->isWalkable($candidate->{x}, $candidate->{y});
+
+			my $distance = distance($candidate, $from_pos);
+			if (!defined $closest_distance || $distance < $closest_distance) {
+				$closest_distance = $distance;
+				@closest_walls = ($candidate);
+			} elsif ($distance == $closest_distance) {
+				push @closest_walls, $candidate;
+			}
+		}
+	}
+
+	return \@closest_walls;
+}
+
 ##
 # manualMove(dx, dy)
 #
diff --git a/src/Network/Receive.pm b/src/Network/Receive.pm
index 7733494419..a933913e86 100644
--- a/src/Network/Receive.pm
+++ b/src/Network/Receive.pm
@@ -2604,6 +2604,22 @@ sub actor_action {
 		if ($args->{sourceID} eq $accountID) {
 			message T("You are sitting.\n") if (!$char->{sitting});
 			$char->{sitting} = 1;
+			if ($ai_v{sitAuto_pendingLook}) {
+				my $pendingLook = delete $ai_v{sitAuto_pendingLook};
+				delete $ai_v{sitAuto_scheduledLook};
+				my $delay = ($pendingLook->{delay} && $pendingLook->{delay} > 0) ? $pendingLook->{delay} : 0;
+				if ($delay > 0) {
+					$ai_v{sitAuto_scheduledLook} = {
+						due => time + $delay,
+						body => $pendingLook->{body},
+						head => $pendingLook->{head},
+					};
+				} elsif (defined $pendingLook->{head}) {
+					Misc::look($pendingLook->{body}, $pendingLook->{head});
+				} elsif (defined $pendingLook->{body}) {
+					Misc::look($pendingLook->{body});
+				}
+			}
 			AI::queue("sitAuto") unless (AI::inQueue("sitAuto")) || $ai_v{sitAuto_forcedBySitCommand};
 		} else {
 			message TF("%s is sitting.\n", getActorName($args->{sourceID})), 'parseMsg_statuslook', 2;