diff --git a/AK/FlyString.cpp b/AK/FlyString.cpp
index 55fb34dd47d..13f08ddfc4e 100644
--- a/AK/FlyString.cpp
+++ b/AK/FlyString.cpp
@@ -50,6 +50,8 @@ FlyString FlyString::from_utf8_without_validation(ReadonlyBytes string)
 
 FlyString::FlyString(String const& string)
 {
+    ASSERT(!string.is_invalid());
+
     if (string.is_short_string()) {
         m_data = string;
         return;
diff --git a/AK/FlyString.h b/AK/FlyString.h
index fd2c21e51a9..a0963e6b831 100644
--- a/AK/FlyString.h
+++ b/AK/FlyString.h
@@ -8,6 +8,7 @@
 
 #include <AK/Error.h>
 #include <AK/Format.h>
+#include <AK/Optional.h>
 #include <AK/Platform.h>
 #include <AK/String.h>
 #include <AK/Traits.h>
@@ -80,12 +81,129 @@ public:
     }
 
 private:
+    friend class Optional<FlyString>;
+
+    explicit FlyString(nullptr_t)
+        : m_data(Detail::StringBase(nullptr))
+    {
+    }
+
     explicit FlyString(Detail::StringBase data)
         : m_data(move(data))
     {
     }
 
     Detail::StringBase m_data;
+
+    bool is_invalid() const { return m_data.is_invalid(); }
+};
+
+template<>
+class Optional<FlyString> : public OptionalBase<FlyString> {
+    template<typename U>
+    friend class Optional;
+
+public:
+    using ValueType = FlyString;
+
+    Optional() = default;
+
+    template<SameAs<OptionalNone> V>
+    Optional(V) { }
+
+    Optional(Optional<FlyString> const& other)
+    {
+        if (other.has_value())
+            m_value = other.m_value;
+    }
+
+    Optional(Optional&& other)
+        : m_value(other.m_value)
+    {
+    }
+
+    template<typename U = FlyString>
+    requires(!IsSame<OptionalNone, RemoveCVReference<U>>)
+    explicit(!IsConvertible<U&&, FlyString>) Optional(U&& value)
+    requires(!IsSame<RemoveCVReference<U>, Optional<FlyString>> && IsConstructible<FlyString, U &&>)
+        : m_value(forward<U>(value))
+    {
+    }
+
+    template<SameAs<OptionalNone> V>
+    Optional& operator=(V)
+    {
+        clear();
+        return *this;
+    }
+
+    Optional& operator=(Optional const& other)
+    {
+        if (this != &other) {
+            clear();
+            m_value = other.m_value;
+        }
+        return *this;
+    }
+
+    Optional& operator=(Optional&& other)
+    {
+        if (this != &other) {
+            clear();
+            m_value = other.m_value;
+        }
+        return *this;
+    }
+
+    template<typename O>
+    ALWAYS_INLINE bool operator==(Optional<O> const& other) const
+    {
+        return has_value() == other.has_value() && (!has_value() || value() == other.value());
+    }
+
+    template<typename O>
+    ALWAYS_INLINE bool operator==(O const& other) const
+    {
+        return has_value() && value() == other;
+    }
+
+    void clear()
+    {
+        m_value = FlyString(nullptr);
+    }
+
+    [[nodiscard]] bool has_value() const
+    {
+        return !m_value.is_invalid();
+    }
+
+    [[nodiscard]] FlyString& value() &
+    {
+        VERIFY(has_value());
+        return m_value;
+    }
+
+    [[nodiscard]] FlyString const& value() const&
+    {
+        VERIFY(has_value());
+        return m_value;
+    }
+
+    [[nodiscard]] FlyString value() &&
+    {
+        return release_value();
+    }
+
+    [[nodiscard]] FlyString release_value()
+    {
+        VERIFY(has_value());
+        FlyString released_value = m_value;
+        clear();
+        return released_value;
+    }
+
+private:
+    FlyString m_value = FlyString(nullptr);
 };
 
 template<>
diff --git a/AK/Forward.h b/AK/Forward.h
index 1bc4d95d37c..68b5af27b55 100644
--- a/AK/Forward.h
+++ b/AK/Forward.h
@@ -125,6 +125,12 @@ class NonnullOwnPtr;
 template<typename T>
 class Optional;
 
+template<>
+class Optional<String>;
+
+template<>
+class Optional<FlyString>;
+
 template<typename T>
 class RefPtr;
 
diff --git a/AK/Optional.h b/AK/Optional.h
index 0e2c39b7f83..1bb6441bcbe 100644
--- a/AK/Optional.h
+++ b/AK/Optional.h
@@ -211,7 +211,7 @@ public:
 
     template<typename U>
     requires(IsConstructible<T, U const&> && !IsSpecializationOf<T, Optional> && !IsSpecializationOf<U, Optional>) ALWAYS_INLINE explicit Optional(Optional<U> const& other)
-        : m_has_value(other.m_has_value)
+        : m_has_value(other.has_value())
     {
         if (other.has_value())
             new (&m_storage) T(other.value());
@@ -219,7 +219,7 @@ public:
 
     template<typename U>
     requires(IsConstructible<T, U &&> && !IsSpecializationOf<T, Optional> && !IsSpecializationOf<U, Optional>) ALWAYS_INLINE explicit Optional(Optional<U>&& other)
-        : m_has_value(other.m_has_value)
+        : m_has_value(other.has_value())
     {
         if (other.has_value())
             new (&m_storage) T(other.release_value());
diff --git a/AK/String.h b/AK/String.h
index 93c04983fe7..9461d16e875 100644
--- a/AK/String.h
+++ b/AK/String.h
@@ -211,6 +211,7 @@ public:
 
 private:
     friend class ::AK::FlyString;
+    friend class Optional<String>;
 
     using ShortString = Detail::ShortString;
 
@@ -218,6 +219,117 @@ private:
         : StringBase(move(base))
     {
     }
+
+    explicit constexpr String(nullptr_t)
+        : StringBase(nullptr)
+    {
+    }
+};
+
+template<>
+class Optional<String> : public OptionalBase<String> {
+    template<typename U>
+    friend class Optional;
+
+public:
+    using ValueType = String;
+
+    Optional() = default;
+
+    template<SameAs<OptionalNone> V>
+    Optional(V) { }
+
+    Optional(Optional<String> const& other)
+    {
+        if (other.has_value())
+            m_value = other.m_value;
+    }
+
+    Optional(Optional&& other)
+        : m_value(move(other.m_value))
+    {
+    }
+
+    template<typename U = String>
+    requires(!IsSame<OptionalNone, RemoveCVReference<U>>)
+    explicit(!IsConvertible<U&&, String>) Optional(U&& value)
+    requires(!IsSame<RemoveCVReference<U>, Optional<String>> && IsConstructible<String, U &&>)
+        : m_value(forward<U>(value))
+    {
+    }
+
+    template<SameAs<OptionalNone> V>
+    Optional& operator=(V)
+    {
+        clear();
+        return *this;
+    }
+
+    Optional& operator=(Optional const& other)
+    {
+        if (this != &other) {
+            m_value = other.m_value;
+        }
+        return *this;
+    }
+
+    Optional& operator=(Optional&& other)
+    {
+        if (this != &other) {
+            m_value = move(other.m_value);
+        }
+        return *this;
+    }
+
+    template<typename O>
+    ALWAYS_INLINE bool operator==(Optional<O> const& other) const
+    {
+        return has_value() == other.has_value() && (!has_value() || value() == other.value());
+    }
+
+    template<typename O>
+    ALWAYS_INLINE bool operator==(O const& other) const
+    {
+        return has_value() && value() == other;
+    }
+
+    void clear()
+    {
+        m_value = String(nullptr);
+    }
+
+    [[nodiscard]] bool has_value() const
+    {
+        return !m_value.is_invalid();
+    }
+
+    [[nodiscard]] String& value() &
+    {
+        VERIFY(has_value());
+        return m_value;
+    }
+
+    [[nodiscard]] String const& value() const&
+    {
+        VERIFY(has_value());
+        return m_value;
+    }
+
+    [[nodiscard]] String value() &&
+    {
+        return release_value();
+    }
+
+    [[nodiscard]] String release_value()
+    {
+        VERIFY(has_value());
+        String released_value = m_value;
+        clear();
+        return released_value;
+    }
+
+private:
+    String m_value { nullptr };
 };
 
 template<>
diff --git a/AK/StringBase.cpp b/AK/StringBase.cpp
index 622266d1764..dd453bc4cf0 100644
--- a/AK/StringBase.cpp
+++ b/AK/StringBase.cpp
@@ -58,6 +58,7 @@ StringBase& StringBase::operator=(StringBase const& other)
 
 ReadonlyBytes StringBase::bytes() const
 {
+    ASSERT(!is_invalid());
     if (is_short_string())
         return m_short_string.bytes();
     return m_data->bytes();
@@ -65,6 +66,7 @@ ReadonlyBytes StringBase::bytes() const
 
 u32 StringBase::hash() const
 {
+    ASSERT(!is_invalid());
     if (is_short_string()) {
         auto bytes = this->bytes();
         return string_hash(reinterpret_cast<char const*>(bytes.data()), bytes.size());
@@ -74,6 +76,7 @@ u32 StringBase::hash() const
 
 size_t StringBase::byte_count() const
 {
+    ASSERT(!is_invalid());
     if (is_short_string())
         return m_short_string.byte_count_and_short_string_flag >> 1;
     return m_data->byte_count();
@@ -81,6 +84,7 @@ size_t StringBase::byte_count() const
 
 bool StringBase::operator==(StringBase const& other) const
 {
+    ASSERT(!is_invalid());
     if (is_short_string())
         return m_data == other.m_data;
     if (other.is_short_string())
@@ -92,6 +96,7 @@ bool StringBase::operator==(StringBase const& other) const
 
 void StringBase::replace_with_string_builder(StringBuilder& builder)
 {
+    ASSERT(!is_invalid());
     if (builder.length() <= MAX_SHORT_STRING_BYTE_COUNT) {
         return replace_with_new_short_string(builder.length(), [&](Bytes buffer) {
             builder.string_view().bytes().copy_to(buffer);
@@ -105,6 +110,7 @@ void StringBase::replace_with_string_builder(StringBuilder& builder)
 
 ErrorOr<Bytes> StringBase::replace_with_uninitialized_buffer(size_t byte_count)
 {
+    ASSERT(!is_invalid());
     if (byte_count <= MAX_SHORT_STRING_BYTE_COUNT)
         return replace_with_uninitialized_short_string(byte_count);
 
@@ -116,6 +122,7 @@ ErrorOr<Bytes> StringBase::replace_with_uninitialized_buffer(size_t byte_count)
 
 ErrorOr<StringBase> StringBase::substring_from_byte_offset_with_shared_superstring(size_t start, size_t length) const
 {
+    ASSERT(!is_invalid());
     VERIFY(start + length <= byte_count());
 
     if (length == 0)
diff --git a/AK/StringBase.h b/AK/StringBase.h
index e6086be2f72..39687e61b94 100644
--- a/AK/StringBase.h
+++ b/AK/StringBase.h
@@ -75,6 +75,8 @@ public:
     [[nodiscard]] ALWAYS_INLINE FlatPtr raw(Badge<FlyString>) const { return bit_cast<FlatPtr>(m_data); }
 
 protected:
+    bool is_invalid() const { return m_invalid_tag == UINTPTR_MAX; }
+
     template<typename Func>
     ErrorOr<void> replace_with_new_string(size_t byte_count, Func&& callback)
     {
@@ -107,6 +109,11 @@ private:
 
     explicit StringBase(NonnullRefPtr<Detail::StringData const>);
 
+    explicit constexpr StringBase(nullptr_t)
+        : m_invalid_tag(UINTPTR_MAX)
+    {
+    }
+
     explicit constexpr StringBase(ShortString short_string)
         : m_short_string(short_string)
     {
@@ -129,6 +136,7 @@ private:
     union {
         ShortString m_short_string;
         Detail::StringData const* m_data { nullptr };
+        uintptr_t m_invalid_tag;
     };
 };
 
diff --git a/Tests/AK/TestOptional.cpp b/Tests/AK/TestOptional.cpp
index e71221b132a..cb17d62debd 100644
--- a/Tests/AK/TestOptional.cpp
+++ b/Tests/AK/TestOptional.cpp
@@ -8,7 +8,9 @@
 #include <LibTest/TestCase.h>
 
 #include <AK/ByteString.h>
+#include <AK/FlyString.h>
 #include <AK/Optional.h>
+#include <AK/String.h>
 #include <AK/Vector.h>
 
 TEST_CASE(basic_optional)
@@ -269,3 +271,173 @@ TEST_CASE(comparison_reference)
     EXPECT_EQ(opt1, opt2);
     EXPECT_NE(opt1, opt3);
 }
+
+TEST_CASE(string_specialization)
+{
+    EXPECT_EQ(sizeof(Optional<String>), sizeof(String));
+
+    {
+        Optional<String> foo;
+
+        EXPECT(!foo.has_value());
+
+        foo = "long_enough_to_be_allocated"_string;
+
+        EXPECT(foo.has_value());
+        EXPECT_EQ(foo.value(), "long_enough_to_be_allocated"sv);
+    }
+
+    {
+        Optional<String> foo = "initial_value"_string;
+
+        EXPECT(foo.has_value());
+        EXPECT_EQ(foo.value(), "initial_value"sv);
+
+        foo = "long_enough_to_be_allocated"_string;
+
+        EXPECT(foo.has_value());
+        EXPECT_EQ(foo.value(), "long_enough_to_be_allocated"sv);
+    }
+
+    {
+        Optional<String> foo;
+
+        EXPECT(!foo.has_value());
+
+        String bar = "long_enough_to_be_allocated"_string;
+        foo = bar;
+
+        EXPECT(foo.has_value());
+        EXPECT_EQ(foo.value(), "long_enough_to_be_allocated"sv);
+    }
+
+    {
+        Optional<String> foo;
+
+        EXPECT(!foo.has_value());
+
+        Optional<String> bar = "long_enough_to_be_allocated"_string;
+        foo = bar;
+
+        EXPECT(foo.has_value());
+        EXPECT_EQ(foo.value(), "long_enough_to_be_allocated"sv);
+        EXPECT(bar.has_value());
+        EXPECT_EQ(bar.value(), "long_enough_to_be_allocated"sv);
+    }
+
+    {
+        Optional<String> foo;
+
+        EXPECT(!foo.has_value());
+
+        foo = Optional<String> { "long_enough_to_be_allocated"_string };
+
+        EXPECT(foo.has_value());
+        EXPECT_EQ(foo.value(), "long_enough_to_be_allocated"sv);
+    }
+
+    {
+        Optional<String> foo = "long_enough_to_be_allocated"_string;
+
+        EXPECT_EQ(foo.value_or("fallback_value"_string), "long_enough_to_be_allocated"sv);
+    }
+
+    {
+        Optional<String> foo;
+
+        EXPECT_EQ(foo.value_or("fallback_value"_string), "fallback_value"sv);
+    }
+
+    {
+        EXPECT_EQ((Optional<String> { "long_enough_to_be_allocated"_string }).value_or("fallback_value"_string), "long_enough_to_be_allocated"sv);
+    }
+
+    {
+        EXPECT_EQ((Optional<String> {}).value_or("fallback_value"_string), "fallback_value"sv);
+    }
+}
+
+TEST_CASE(flystring_specialization)
+{
+    EXPECT_EQ(sizeof(Optional<FlyString>), sizeof(FlyString));
+
+    {
+        Optional<FlyString> foo;
+
+        EXPECT(!foo.has_value());
+
+        foo = "long_enough_to_be_allocated"_fly_string;
+
+        EXPECT(foo.has_value());
+        EXPECT_EQ(foo.value(), "long_enough_to_be_allocated"sv);
+    }
+
+    {
+        Optional<FlyString> foo = "initial_value"_fly_string;
+
+        EXPECT(foo.has_value());
+        EXPECT_EQ(foo.value(), "initial_value"sv);
+
+        foo = "long_enough_to_be_allocated"_fly_string;
+
+        EXPECT(foo.has_value());
+        EXPECT_EQ(foo.value(), "long_enough_to_be_allocated"sv);
+    }
+
+    {
+        Optional<FlyString> foo;
+
+        EXPECT(!foo.has_value());
+
+        FlyString bar = "long_enough_to_be_allocated"_fly_string;
+        foo = bar;
+
+        EXPECT(foo.has_value());
+        EXPECT_EQ(foo.value(), "long_enough_to_be_allocated"sv);
+    }
+
+    {
+        Optional<FlyString> foo;
+
+        EXPECT(!foo.has_value());
+
+        Optional<FlyString> bar = "long_enough_to_be_allocated"_fly_string;
+        foo = bar;
+
+        EXPECT(bar.has_value());
+        EXPECT_EQ(bar.value(), "long_enough_to_be_allocated"sv);
+        EXPECT(foo.has_value());
+        EXPECT_EQ(foo.value(), "long_enough_to_be_allocated"sv);
+    }
+
+    {
+        Optional<FlyString> foo;
+
+        EXPECT(!foo.has_value());
+
+        foo = Optional<FlyString> { "long_enough_to_be_allocated"_fly_string };
+
+        EXPECT(foo.has_value());
+        EXPECT_EQ(foo.value(), "long_enough_to_be_allocated"sv);
+    }
+
+    {
+        Optional<FlyString> foo = "long_enough_to_be_allocated"_fly_string;
+
+        EXPECT_EQ(foo.value_or("fallback_value"_fly_string), "long_enough_to_be_allocated"sv);
+    }
+
+    {
+        Optional<FlyString> foo;
+
+        EXPECT_EQ(foo.value_or("fallback_value"_fly_string), "fallback_value"sv);
+    }
+
+    {
+        EXPECT_EQ((Optional<FlyString> { "long_enough_to_be_allocated"_fly_string }).value_or("fallback_value"_fly_string), "long_enough_to_be_allocated"sv);
+    }
+
+    {
+        EXPECT_EQ((Optional<FlyString> {}).value_or("fallback_value"_fly_string), "fallback_value"sv);
+    }
+}