diff --git a/src/repl/eval.zig b/src/repl/eval.zig
index 76aa445ec2..d80a1aee43 100644
--- a/src/repl/eval.zig
+++ b/src/repl/eval.zig
@@ -239,12 +239,15 @@ pub const Repl = struct {
                 return try std.fmt.allocPrint(self.allocator, "assigned `{s}`", .{info.var_name});
             },
             .type_annotation => |info| {
-                // Store the type annotation for future use
+                // For type annotations:
+                // 1. Store them as definitions for future use
                 try self.addOrReplaceDefinition(info.source, info.var_name);
 
-                // Type annotations alone cannot be evaluated - they create e_anno_only which crashes when used
-                // Return a message indicating the annotation was stored
-                return try std.fmt.allocPrint(self.allocator, "Crash: runtime error", .{});
+                // 2. Evaluate the full source (including all definitions + this annotation)
+                //    This will create an e_anno_only which will crash when evaluated
+                const full_source = try self.buildFullSource(input);
+                defer self.allocator.free(full_source);
+                return try self.evaluateSource(full_source);
             },
             .import => {
                 // Imports are not supported in this implementation
diff --git a/src/repl/repl_test.zig b/src/repl/repl_test.zig
index 4aab7548d3..1157d70b54 100644
--- a/src/repl/repl_test.zig
+++ b/src/repl/repl_test.zig
@@ -402,10 +402,10 @@ test "Repl - standalone annotation should crash, then call should fail - REGRESS
     const result2 = try repl.step("foo(\"test\")");
     defer std.testing.allocator.free(result2);
 
-    // Should return a canonicalization error since foo only has a type annotation, no definition
-    if (std.mem.indexOf(u8, result2, "Canonicalize expr error") == null) {
-        std.debug.print("\nexpected Canonicalize expr error, got: {s}\n", .{result2});
+    // Should return "Evaluation error: error.TypeMismatch"
+    if (std.mem.indexOf(u8, result2, "TypeMismatch") == null) {
+        std.debug.print("\nexpected TypeMismatch, got: {s}\n", .{result2});
         return error.TestUnexpectedResult;
     }
-    try testing.expect(std.mem.indexOf(u8, result2, "expression returned null for apply") != null);
+    try testing.expect(std.mem.indexOf(u8, result2, "Evaluation error") != null);
 }
diff --git a/test/snapshots/repl/anno_only_crash.md b/test/snapshots/repl/anno_only_crash.md
index a3f49c8cbc..efdda51bcc 100644
--- a/test/snapshots/repl/anno_only_crash.md
+++ b/test/snapshots/repl/anno_only_crash.md
@@ -11,6 +11,6 @@ type=repl
 # OUTPUT
 Crash: runtime error
 ---
-Canonicalize expr error: expression returned null for apply
+Evaluation error: error.TypeMismatch
 # PROBLEMS
 NIL