diff --git a/Userland/Libraries/LibJS/JIT/Assembler.h b/Userland/Libraries/LibJS/JIT/Assembler.h
index b1a4832708..752c9eaf2a 100644
--- a/Userland/Libraries/LibJS/JIT/Assembler.h
+++ b/Userland/Libraries/LibJS/JIT/Assembler.h
@@ -37,6 +37,8 @@ struct Assembler {
     struct Operand {
         enum class Type {
             Reg,
+            Imm8,
+            Imm32,
             Imm64,
             Mem64BaseAndOffset,
         };
@@ -54,6 +56,22 @@ struct Assembler {
             return operand;
         }
 
+        static Operand Imm8(u8 imm8)
+        {
+            Operand operand;
+            operand.type = Type::Imm8;
+            operand.offset_or_immediate = imm8;
+            return operand;
+        }
+
+        static Operand Imm32(u32 imm32)
+        {
+            Operand operand;
+            operand.type = Type::Imm32;
+            operand.offset_or_immediate = imm32;
+            return operand;
+        }
+
         static Operand Imm64(u64 imm64)
         {
             Operand operand;
@@ -77,6 +95,16 @@ struct Assembler {
         return to_underlying(reg) & 0x7;
     }
 
+    void shift_right(Operand dst, Operand count)
+    {
+        VERIFY(dst.type == Operand::Type::Reg);
+        VERIFY(count.type == Operand::Type::Imm8);
+        emit8(0x48 | ((to_underlying(dst.reg) >= 8) ? 1 << 0 : 0));
+        emit8(0xc1);
+        emit8(0xe8 | encode_reg(dst.reg));
+        emit8(count.offset_or_immediate);
+    }
+
     void mov(Operand dst, Operand src)
     {
         if (dst.type == Operand::Type::Reg && src.type == Operand::Type::Reg) {
@@ -176,6 +204,33 @@ struct Assembler {
         emit8(0xc0 | (to_underlying(dst) << 3) | to_underlying(dst));
     }
 
+    struct Label {
+        size_t offset_in_instruction_stream { 0 };
+
+        void link(Assembler& assembler)
+        {
+            auto offset = assembler.m_output.size() - offset_in_instruction_stream;
+            auto jump_slot = offset_in_instruction_stream - 4;
+            assembler.m_output[jump_slot + 0] = (offset >> 0) & 0xff;
+            assembler.m_output[jump_slot + 1] = (offset >> 8) & 0xff;
+            assembler.m_output[jump_slot + 2] = (offset >> 16) & 0xff;
+            assembler.m_output[jump_slot + 3] = (offset >> 24) & 0xff;
+        }
+    };
+
+    [[nodiscard]] Label make_label()
+    {
+        return { .offset_in_instruction_stream = m_output.size() };
+    }
+
+    [[nodiscard]] Label jump()
+    {
+        // jmp target (RIP-relative 32-bit offset)
+        emit8(0xe9);
+        emit32(0xdeadbeef);
+        return make_label();
+    }
+
     void jump(Bytecode::BasicBlock& target)
     {
         // jmp target (RIP-relative 32-bit offset)
@@ -203,6 +258,50 @@ struct Assembler {
         jump(true_target);
     }
 
+    void jump_if_not_equal(Operand lhs, Operand rhs, Label& label)
+    {
+        // cmp lhs, rhs
+        if (lhs.type == Operand::Type::Reg && rhs.type == Operand::Type::Reg) {
+            emit8(0x48
+                | ((to_underlying(lhs.reg) >= 8) ? 1 << 2 : 0)
+                | ((to_underlying(rhs.reg) >= 8) ? 1 << 0 : 0));
+            emit8(0x39);
+            emit8(0xc0 | (encode_reg(lhs.reg) << 3) | encode_reg(rhs.reg));
+        } else if (lhs.type == Operand::Type::Reg && rhs.type == Operand::Type::Imm32) {
+            emit8(0x48 | ((to_underlying(lhs.reg) >= 8) ? 1 << 0 : 0));
+            emit8(0x81);
+            emit8(0xf8 | encode_reg(lhs.reg));
+            emit32(rhs.offset_or_immediate);
+        } else {
+            VERIFY_NOT_REACHED();
+        }
+
+        // jne label (RIP-relative 32-bit offset)
+        emit8(0x0f);
+        emit8(0x85);
+        emit32(0xdeadbeef);
+        label.offset_in_instruction_stream = m_output.size();
+    }
+
+    void bitwise_and(Operand dst, Operand src)
+    {
+        // and dst,src
+        if (dst.type == Operand::Type::Reg && src.type == Operand::Type::Reg) {
+            emit8(0x48
+                | ((to_underlying(dst.reg) >= 8) ? 1 << 2 : 0)
+                | ((to_underlying(src.reg) >= 8) ? 1 << 0 : 0));
+            emit8(0x21);
+            emit8(0xc0 | (encode_reg(dst.reg) << 3) | encode_reg(src.reg));
+        } else if (dst.type == Operand::Type::Reg && src.type == Operand::Type::Imm32) {
+            emit8(0x48 | ((to_underlying(dst.reg) >= 8) ? 1 << 0 : 0));
+            emit8(0x81);
+            emit8(0xe0 | encode_reg(dst.reg));
+            emit32(src.offset_or_immediate);
+        } else {
+            VERIFY_NOT_REACHED();
+        }
+    }
+
     void exit()
     {
         // ret
diff --git a/Userland/Libraries/LibJS/JIT/Compiler.cpp b/Userland/Libraries/LibJS/JIT/Compiler.cpp
index 6066b06971..31e10d5ff2 100644
--- a/Userland/Libraries/LibJS/JIT/Compiler.cpp
+++ b/Userland/Libraries/LibJS/JIT/Compiler.cpp
@@ -82,22 +82,59 @@ static bool cxx_to_boolean(VM&, Value value)
     return value.to_boolean();
 }
 
-void Compiler::compile_to_boolean(Assembler::Reg reg)
+void Compiler::compile_to_boolean(Assembler::Reg dst, Assembler::Reg src)
 {
+    // dst = src;
+    m_assembler.mov(
+        Assembler::Operand::Register(dst),
+        Assembler::Operand::Register(src));
+
+    // dst >>= 48;
+    m_assembler.shift_right(
+        Assembler::Operand::Register(dst),
+        Assembler::Operand::Imm8(48));
+
+    // if (dst != BOOLEAN_TAG) goto slow_case;
+    auto slow_case = m_assembler.make_label();
+    m_assembler.jump_if_not_equal(
+        Assembler::Operand::Register(dst),
+        Assembler::Operand::Imm32(BOOLEAN_TAG),
+        slow_case);
+
+    // Fast path for JS::Value booleans.
+
+    // dst = src;
+    m_assembler.mov(
+        Assembler::Operand::Register(dst),
+        Assembler::Operand::Register(src));
+
+    // dst &= 1;
+    m_assembler.bitwise_and(
+        Assembler::Operand::Register(dst),
+        Assembler::Operand::Imm32(1));
+
+    // goto end;
+    auto end = m_assembler.jump();
+
+    // slow_case: // call C++ helper
+    slow_case.link(m_assembler);
     m_assembler.mov(
         Assembler::Operand::Register(Assembler::Reg::Arg1),
-        Assembler::Operand::Register(reg));
+        Assembler::Operand::Register(src));
     m_assembler.native_call((void*)cxx_to_boolean);
     m_assembler.mov(
-        Assembler::Operand::Register(reg),
+        Assembler::Operand::Register(dst),
         Assembler::Operand::Register(Assembler::Reg::Ret));
+
+    // end:
+    end.link(m_assembler);
 }
 
 void Compiler::compile_jump_conditional(Bytecode::Op::JumpConditional const& op)
 {
-    load_vm_register(Assembler::Reg::GPR0, Bytecode::Register::accumulator());
+    load_vm_register(Assembler::Reg::GPR1, Bytecode::Register::accumulator());
 
-    compile_to_boolean(Assembler::Reg::GPR0);
+    compile_to_boolean(Assembler::Reg::GPR0, Assembler::Reg::GPR1);
 
     m_assembler.jump_conditional(Assembler::Reg::GPR0,
         const_cast<Bytecode::BasicBlock&>(op.true_target()->block()),
diff --git a/Userland/Libraries/LibJS/JIT/Compiler.h b/Userland/Libraries/LibJS/JIT/Compiler.h
index 9139ff3b0e..5840df8b42 100644
--- a/Userland/Libraries/LibJS/JIT/Compiler.h
+++ b/Userland/Libraries/LibJS/JIT/Compiler.h
@@ -34,7 +34,7 @@ private:
     void store_vm_local(size_t, Assembler::Reg);
     void load_vm_local(Assembler::Reg, size_t);
 
-    void compile_to_boolean(Assembler::Reg);
+    void compile_to_boolean(Assembler::Reg dst, Assembler::Reg src);
 
     Vector<u8> m_output;
     Assembler m_assembler { m_output };