diff --git a/AK/CircularBuffer.cpp b/AK/CircularBuffer.cpp
index 7e38361a847..8c6034ccbc0 100644
--- a/AK/CircularBuffer.cpp
+++ b/AK/CircularBuffer.cpp
@@ -60,15 +60,15 @@ Optional<size_t> CircularBuffer::offset_of(StringView needle, Optional<size_t> f
 
     Array<ReadonlyBytes, 2> spans {};
     spans[0] = next_read_span();
+    auto const original_span_0_size = spans[0].size();
 
     if (read_from > 0)
         spans[0] = spans[0].slice(min(spans[0].size(), read_from));
 
     if (spans[0].size() + read_from > read_until)
         spans[0] = spans[0].trim(read_until - read_from);
-
-    if (is_wrapping_around())
-        spans[1] = m_buffer.span().slice(max(spans[0].size(), read_from) - spans[0].size(), min(read_until, m_used_space) - spans[0].size());
+    else if (is_wrapping_around())
+        spans[1] = m_buffer.span().slice(max(original_span_0_size, read_from) - original_span_0_size, min(read_until, m_used_space) - original_span_0_size);
 
     auto maybe_found = AK::memmem(spans.begin(), spans.end(), needle.bytes());
     if (maybe_found.has_value())
diff --git a/Tests/AK/TestCircularBuffer.cpp b/Tests/AK/TestCircularBuffer.cpp
index 8bab0233c24..5551d72d3ca 100644
--- a/Tests/AK/TestCircularBuffer.cpp
+++ b/Tests/AK/TestCircularBuffer.cpp
@@ -310,6 +310,41 @@ TEST_CASE(offset_of_with_until_and_after)
     result = circular_buffer.offset_of("o Frie"sv, 4, 10);
     EXPECT_EQ(result.value_or(42), 4ul);
 
-    result = circular_buffer.offset_of("el"sv, 3, 14);
+    result = circular_buffer.offset_of("el"sv, 3, 17);
     EXPECT_EQ(result.value_or(42), 15ul);
 }
+
+TEST_CASE(offset_of_with_until_and_after_wrapping_around)
+{
+    auto const source = "Well Hello Friends!"sv;
+    auto byte_buffer_or_error = ByteBuffer::copy(source.bytes());
+    EXPECT(!byte_buffer_or_error.is_error());
+    auto byte_buffer = byte_buffer_or_error.release_value();
+
+    auto circular_buffer_or_error = CircularBuffer::create_empty(19);
+    EXPECT(!circular_buffer_or_error.is_error());
+    auto circular_buffer = circular_buffer_or_error.release_value();
+
+    auto written_bytes = circular_buffer.write(byte_buffer.span().trim(5));
+    EXPECT_EQ(written_bytes, 5ul);
+
+    auto result = circular_buffer.offset_of("Well "sv, 0, 5);
+    EXPECT_EQ(result.value_or(42), 0ul);
+
+    written_bytes = circular_buffer.write(byte_buffer.span().slice(5));
+    EXPECT_EQ(written_bytes, 14ul);
+
+    result = circular_buffer.offset_of("Hello Friends!"sv, 5, 19);
+    EXPECT_EQ(result.value_or(42), 5ul);
+
+    safe_discard(circular_buffer, 5);
+
+    result = circular_buffer.offset_of("Hello Friends!"sv, 0, 14);
+    EXPECT_EQ(result.value_or(42), 0ul);
+
+    written_bytes = circular_buffer.write(byte_buffer.span().trim(5));
+    EXPECT_EQ(written_bytes, 5ul);
+
+    result = circular_buffer.offset_of("Well "sv, 14, 19);
+    EXPECT_EQ(result.value_or(42), 14ul);
+}