diff --git a/crates/oxide_vm/src/coercion.rs b/crates/oxide_vm/src/coercion.rs
index e07b811..d62f39b 100644
--- a/crates/oxide_vm/src/coercion.rs
+++ b/crates/oxide_vm/src/coercion.rs
@@ -81,7 +81,7 @@ pub fn to_string(string_forge: &StringForge, val: JsValue) -> String {
     String::new()
 }
 
-pub fn to_boolean(val: JsValue) -> bool {
+pub fn to_boolean(val: JsValue, string_forge: &StringForge) -> bool {
     if val.is_undefined() || val.is_null() {
         return false;
     }
@@ -96,7 +96,10 @@ pub fn to_boolean(val: JsValue) -> bool {
         return !(d == 0.0 || d == -0.0 || d.is_nan());
     }
     if val.is_string() {
-        return true;
+        let s = string_forge
+            .lookup(val.as_string_index())
+            .unwrap_or_default();
+        return !s.is_empty();
     }
     if val.is_object() {
         return true;
diff --git a/crates/oxide_vm/src/vm.rs b/crates/oxide_vm/src/vm.rs
index e210187..f132a90 100644
--- a/crates/oxide_vm/src/vm.rs
+++ b/crates/oxide_vm/src/vm.rs
@@ -259,7 +259,8 @@ impl Vm {
                 }
 
                 OpCode::JMP_IF_FALSE => {
-                    let cond = coercion::to_boolean(self.regs[rd]);
+                    let cond =
+                        coercion::to_boolean(self.regs[rd], self.kernel.string_forge().as_ref());
                     if !cond {
                         let offset = opcode::offset16(instr) as isize;
                         self.pc = ((self.pc as isize) + offset - 1) as usize;
@@ -267,7 +268,8 @@ impl Vm {
                 }
 
                 OpCode::JMP_IF_TRUE => {
-                    let cond = coercion::to_boolean(self.regs[rd]);
+                    let cond =
+                        coercion::to_boolean(self.regs[rd], self.kernel.string_forge().as_ref());
                     if cond {
                         let offset = opcode::offset16(instr) as isize;
                         self.pc = ((self.pc as isize) + offset - 1) as usize;
@@ -547,17 +549,20 @@ impl Vm {
                 }
 
                 OpCode::NOT => {
-                    let cond = coercion::to_boolean(self.regs[a]);
+                    let cond =
+                        coercion::to_boolean(self.regs[a], self.kernel.string_forge().as_ref());
                     self.regs[rd] = JsValue::bool(!cond);
                 }
 
                 OpCode::AND => {
-                    let cond = coercion::to_boolean(self.regs[a]);
+                    let cond =
+                        coercion::to_boolean(self.regs[a], self.kernel.string_forge().as_ref());
                     self.regs[rd] = if cond { self.regs[b] } else { self.regs[a] };
                 }
 
                 OpCode::OR => {
-                    let cond = coercion::to_boolean(self.regs[a]);
+                    let cond =
+                        coercion::to_boolean(self.regs[a], self.kernel.string_forge().as_ref());
                     self.regs[rd] = if cond { self.regs[a] } else { self.regs[b] };
                 }