diff --git a/src/value.ts b/src/value.ts
index e52115a..d1f1d3e 100644
--- a/src/value.ts
+++ b/src/value.ts
@@ -65,7 +65,15 @@ export function toValue(v: any, vm?: VM): Value /* throws */ {
     case 'function':
       if ((v as any)[REEF_FUNCTION])
         return (v as any)[REEF_FUNCTION]
-      if (!vm) throw new Error("can't toValue() function without a vm")
+      if (!vm) {
+        const fnName = v.name || '<anonymous>'
+        const fnStr = v.toString().slice(0, 100)
+        throw new Error(
+          `can't toValue() function without a vm\n` +
+          `  Function: ${fnName}\n` +
+          `  Source: ${fnStr}${v.toString().length > 100 ? '...' : ''}\n`
+        )
+      }
       return { type: 'native', fn: wrapNative(vm, v), value: '<function>' }
     case 'object':
       const dict: Dict = new Map()
@@ -180,7 +188,14 @@ export function fromValue(v: Value, vm?: VM): any {
     case 'regex':
       return v.value
     case 'function':
-      if (!vm || !(vm instanceof VM)) throw new Error('VM is required for function conversion')
+      if (!vm || !(vm instanceof VM)) {
+        throw new Error(
+          `VM is required for function conversion\n` +
+          `  Function params: [${v.params.join(', ')}]\n` +
+          `  Function body at instruction: ${v.body}\n` +
+          `  Tip: Pass a VM instance as the second argument to fromValue()`
+        )
+      }
       return fnFromValue(v, vm)
     case 'native':
       return getOriginalFunction(v.fn)
diff --git a/tests/value.test.ts b/tests/value.test.ts
index 22f42f5..c662de1 100644
--- a/tests/value.test.ts
+++ b/tests/value.test.ts
@@ -168,19 +168,70 @@ test("fromValue - async native function roundtrip", async () => {
   const bytecode = toBytecode([["HALT"]])
   const vm = new VM(bytecode)
 
-  // Create an async native function
   const asyncFn = async (x: number, y: number) => {
     await new Promise(resolve => setTimeout(resolve, 1))
     return x + y
   }
 
-  // Roundtrip through Value
   const nativeValue = toValue(asyncFn, vm)
   expect(nativeValue.type).toBe("native")
 
   const roundtrippedFn = fromValue(nativeValue, vm)
 
-  // Verify it works
   const result = await roundtrippedFn(5, 7)
   expect(result).toBe(12)
 })
+
+test("toValue - throws helpful error when converting function without VM", () => {
+  function myFunction(x: number) {
+    return x * 2
+  }
+
+  expect(() => toValue(myFunction)).toThrow(/can't toValue\(\) function without a vm/)
+  expect(() => toValue(myFunction)).toThrow(/Function: myFunction/)
+  expect(() => toValue(myFunction)).toThrow(/Source:/)
+  expect(() => toValue(myFunction)).toThrow(/Tip: Pass a VM instance/)
+})
+
+test("toValue - error message shows function name from binding", () => {
+  const anonymousFn = (x: number) => x * 2
+
+  expect(() => toValue(anonymousFn)).toThrow(/Function: anonymousFn/)
+  expect(() => toValue(anonymousFn)).toThrow(/Source:/)
+})
+
+test("toValue - error when function is nested in object without VM", () => {
+  const obj = {
+    name: "test",
+    handler: (x: number) => x * 2
+  }
+
+  expect(() => toValue(obj)).toThrow(/can't toValue\(\) function without a vm/)
+  expect(() => toValue(obj)).toThrow(/Function: handler/)
+})
+
+test("toValue - error when function is nested in array without VM", () => {
+  const arr = [1, 2, (x: number) => x * 2]
+
+  expect(() => toValue(arr)).toThrow(/can't toValue\(\) function without a vm/)
+})
+
+test("fromValue - throws helpful error when converting function without VM", async () => {
+  const { Scope, fromValue } = await import("#reef")
+
+  const reefFunction = {
+    type: 'function' as const,
+    params: ['x', 'y'],
+    defaults: {},
+    body: 10,
+    parentScope: new Scope(),
+    variadic: false,
+    named: false,
+    value: '<function>' as const
+  }
+
+  expect(() => fromValue(reefFunction)).toThrow(/VM is required for function conversion/)
+  expect(() => fromValue(reefFunction)).toThrow(/Function params: \[x, y\]/)
+  expect(() => fromValue(reefFunction)).toThrow(/Function body at instruction: 10/)
+  expect(() => fromValue(reefFunction)).toThrow(/Tip: Pass a VM instance/)
+})