diff --git a/examples/tests/invalid/inference.w b/examples/tests/invalid/inference.w
index 39a3a6d32d3..11b173a0493 100644
--- a/examples/tests/invalid/inference.w
+++ b/examples/tests/invalid/inference.w
@@ -80,4 +80,7 @@ class NeedAnnotations {
 //     ^^^^ Missing required type annotation for method signature
     log(nice);
   }
-}
\ No newline at end of file
+}
+
+let badFunc: inflight (str): void = inflight (arg1: num) => {};
+//                                  ^^^^^^^^^^^^^^^^^^^^^^^^^^ Expected type to be "inflight (str): void", but got "inflight (arg1: num): unknown" instead
diff --git a/libs/wingc/src/type_check.rs b/libs/wingc/src/type_check.rs
index 5b9e3809180..7b96e49b602 100644
--- a/libs/wingc/src/type_check.rs
+++ b/libs/wingc/src/type_check.rs
@@ -2419,7 +2419,8 @@ impl<'a> TypeChecker<'a> {
 		if expected_types.len() == 1 {
 			// First check if the actual type is an inference that can be replaced with the expected type
 			if self.add_new_inference(&actual_type, &expected_types[0]) {
-				return_type = expected_types[0];
+				// Update the type we validate and return
+				return_type = self.types.maybe_unwrap_inference(return_type);
 			} else {
 				// otherwise, check if the expected type is an inference that can be replaced with the actual type
 				self.add_new_inference(&expected_types[0], &actual_type);
diff --git a/tools/hangar/__snapshots__/invalid.ts.snap b/tools/hangar/__snapshots__/invalid.ts.snap
index 16d181e64db..91904806b2d 100644
--- a/tools/hangar/__snapshots__/invalid.ts.snap
+++ b/tools/hangar/__snapshots__/invalid.ts.snap
@@ -437,6 +437,17 @@ exports[`cloud_function_expects_inflight.w 1`] = `
   | \\\\-^ Expected type to be \\"inflight (event: str): void\\", but got \\"preflight (name: str): str\\" instead
 
 
+error: Expected type to be \\"inflight (message: str): void\\", but got \\"inflight (x: num): unknown\\" instead
+   --> ../../../examples/tests/invalid/cloud_function_expects_inflight.w:9:15
+   |  
+ 9 |   q.setConsumer(inflight (x: num) => {
+   | /---------------^
+10 | |                      // ^ \\"num\\" doesn't match the expected type \\"str\\"
+11 | |   return;
+12 | | });
+   | \\\\-^ Expected type to be \\"inflight (message: str): void\\", but got \\"inflight (x: num): unknown\\" instead
+
+
  
  
 Tests 1 failed (1)
@@ -882,6 +893,13 @@ error: Expected \\"Json\\" elements to be Json values (https://www.json.org/json
    |              ^^^^^^^^^^^^^^^^^ Expected \\"Json\\" elements to be Json values (https://www.json.org/json-en.html), but got \\"Array<unknown>\\" which is not a Json value
 
 
+error: Expected type to be \\"inflight (str): void\\", but got \\"inflight (arg1: num): unknown\\" instead
+   --> ../../../examples/tests/invalid/inference.w:85:37
+   |
+85 | let badFunc: inflight (str): void = inflight (arg1: num) => {};
+   |                                     ^^^^^^^^^^^^^^^^^^^^^^^^^^ Expected type to be \\"inflight (str): void\\", but got \\"inflight (arg1: num): unknown\\" instead
+
+
 error: Unexpected return value from void function. Return type annotations are required for methods.
    --> ../../../examples/tests/invalid/inference.w:76:5
    |