diff --git a/src/terminal/search/screen.zig b/src/terminal/search/screen.zig
index 179e7da87..c3f48b422 100644
--- a/src/terminal/search/screen.zig
+++ b/src/terminal/search/screen.zig
@@ -1,6 +1,7 @@
 const std = @import("std");
 const assert = @import("../../quirks.zig").inlineAssert;
 const testing = std.testing;
+const tripwire = @import("../../tripwire.zig");
 const Allocator = std.mem.Allocator;
 const point = @import("../point.zig");
 const highlight = @import("../highlight.zig");
@@ -17,6 +18,11 @@ const SlidingWindow = @import("sliding_window.zig").SlidingWindow;
 
 const log = std.log.scoped(.search_screen);
 
+const reloadActive_tw = tripwire.module(enum {
+    history_append_new,
+    history_append_existing,
+}, ScreenSearch.reloadActive);
+
 /// Searches for a needle within a Screen, handling active area updates,
 /// pages being pruned from the screen (e.g. scrollback limits), and more.
 ///
@@ -386,6 +392,8 @@ pub const ScreenSearch = struct {
     ///
     /// The caller must hold the necessary locks to access the screen state.
     pub fn reloadActive(self: *ScreenSearch) Allocator.Error!void {
+        const tw = reloadActive_tw;
+
         // If our selection pin became garbage it means we scrolled off
         // the end. Clear our selection and on exit of this function,
         // try to select the last match.
@@ -485,12 +493,16 @@ pub const ScreenSearch = struct {
                 alloc,
                 self.history_results.items.len,
             );
-            errdefer results.deinit(alloc);
+            errdefer {
+                for (results.items) |*hl| hl.deinit(alloc);
+                results.deinit(alloc);
+            }
             while (window.next()) |hl| {
                 if (hl.chunks.items(.node)[0] == history_node) continue;
 
                 var hl_cloned = try hl.clone(alloc);
                 errdefer hl_cloned.deinit(alloc);
+                try tw.check(.history_append_new);
                 try results.append(alloc, hl_cloned);
             }
 
@@ -505,6 +517,7 @@ pub const ScreenSearch = struct {
             // Matches! Reverse our list then append all the remaining
             // history items that didn't start on our original node.
             std.mem.reverse(FlattenedHighlight, results.items);
+            try tw.check(.history_append_existing);
             try results.appendSlice(alloc, self.history_results.items);
             self.history_results.deinit(alloc);
             self.history_results = results;
@@ -1408,3 +1421,96 @@ test "screen search no scrollback has no history" {
     defer alloc.free(matches);
     try testing.expectEqual(0, matches.len);
 }
+
+test "reloadActive partial history cleanup on appendSlice error" {
+    // This test verifies that when reloadActive fails at appendSlice (after
+    // the loop), all FlattenedHighlight items are properly cleaned up.
+    const alloc = testing.allocator;
+    var t: Terminal = try .init(alloc, .{
+        .cols = 10,
+        .rows = 2,
+        .max_scrollback = std.math.maxInt(usize),
+    });
+    defer t.deinit(alloc);
+    const list: *PageList = &t.screens.active.pages;
+
+    var s = t.vtStream();
+    defer s.deinit();
+
+    // Write multiple "Fizz" matches that will end up in history.
+    // We need enough content to push "Fizz" entries into scrollback.
+    try s.nextSlice("Fizz\r\nFizz\r\n");
+    while (list.totalPages() < 3) try s.nextSlice("\r\n");
+    for (0..list.rows) |_| try s.nextSlice("\r\n");
+    try s.nextSlice("Fizz.");
+
+    // Complete initial search
+    var search: ScreenSearch = try .init(alloc, t.screens.active, "Fizz");
+    defer search.deinit();
+    try search.searchAll();
+
+    // Now trigger reloadActive by adding more content that changes the
+    // active/history boundary. First add more "Fizz" entries to history.
+    try s.nextSlice("\r\nFizz\r\nFizz\r\n");
+    while (list.totalPages() < 4) try s.nextSlice("\r\n");
+    for (0..list.rows) |_| try s.nextSlice("\r\n");
+
+    // Arm the tripwire to fail at appendSlice (after the loop completes).
+    // At this point, there are FlattenedHighlight items in the results list
+    // that need cleanup.
+    const tw = reloadActive_tw;
+    defer tw.end(.reset) catch unreachable;
+    try tw.errorAlways(.history_append_existing, error.OutOfMemory);
+
+    // reloadActive is called by select(), which should trigger the error path.
+    // If the bug exists, testing.allocator will report a memory leak
+    // because FlattenedHighlight items weren't cleaned up.
+    try testing.expectError(error.OutOfMemory, search.select(.next));
+}
+
+test "reloadActive partial history cleanup on loop append error" {
+    // This test verifies that when reloadActive fails inside the loop
+    // (after some items have been appended), all FlattenedHighlight items
+    // are properly cleaned up.
+    const alloc = testing.allocator;
+    var t: Terminal = try .init(alloc, .{
+        .cols = 10,
+        .rows = 2,
+        .max_scrollback = std.math.maxInt(usize),
+    });
+    defer t.deinit(alloc);
+    const list: *PageList = &t.screens.active.pages;
+
+    var s = t.vtStream();
+    defer s.deinit();
+
+    // Write multiple "Fizz" matches that will end up in history.
+    // We need enough content to push "Fizz" entries into scrollback.
+    try s.nextSlice("Fizz\r\nFizz\r\n");
+    while (list.totalPages() < 3) try s.nextSlice("\r\n");
+    for (0..list.rows) |_| try s.nextSlice("\r\n");
+    try s.nextSlice("Fizz.");
+
+    // Complete initial search
+    var search: ScreenSearch = try .init(alloc, t.screens.active, "Fizz");
+    defer search.deinit();
+    try search.searchAll();
+
+    // Now trigger reloadActive by adding more content that changes the
+    // active/history boundary. First add more "Fizz" entries to history.
+    try s.nextSlice("\r\nFizz\r\nFizz\r\n");
+    while (list.totalPages() < 4) try s.nextSlice("\r\n");
+    for (0..list.rows) |_| try s.nextSlice("\r\n");
+
+    // Arm the tripwire to fail after the first loop append succeeds.
+    // This leaves at least one FlattenedHighlight in the results list
+    // that needs cleanup.
+    const tw = reloadActive_tw;
+    defer tw.end(.reset) catch unreachable;
+    try tw.errorAfter(.history_append_new, error.OutOfMemory, 1);
+
+    // reloadActive is called by select(), which should trigger the error path.
+    // If the bug exists, testing.allocator will report a memory leak
+    // because FlattenedHighlight items weren't cleaned up.
+    try testing.expectError(error.OutOfMemory, search.select(.next));
+}