diff --git a/releasenotes.md b/releasenotes.md
index 0755711b6..8e290f74e 100644
--- a/releasenotes.md
+++ b/releasenotes.md
@@ -57,6 +57,7 @@
 - Linking fails on operator method imported as `@public` #2224.
 - Lambda C-style vaargs were not properly rejected, leading to crash #2229.
 - Incorrect handling of constant null fault causing compiler crash #2232.
+- Overload resolution fixes to inline typedef #2226.
 
 ### Stdlib changes
 - Deprecate `String.is_zstr` and `String.quick_zstr` #2188.
diff --git a/src/compiler/sema_const.c b/src/compiler/sema_const.c
index 851c1dfd1..3ed085605 100644
--- a/src/compiler/sema_const.c
+++ b/src/compiler/sema_const.c
@@ -291,6 +291,7 @@ static inline ConstInitializer *expr_const_initializer_from_expr(Expr *expr)
 	}
 }
 
+
 /**
  * The following valid cases exist:
  *
@@ -303,14 +304,11 @@ static inline ConstInitializer *expr_const_initializer_from_expr(Expr *expr)
  */
 bool sema_expr_analyse_ct_concat(SemaContext *context, Expr *concat_expr, Expr *left, Expr *right, bool *failed_ref)
 {
-	ASSERT(concat_expr->resolve_status == RESOLVE_RUNNING);
+	ASSERT_SPAN(concat_expr, concat_expr->resolve_status == RESOLVE_RUNNING);
+	if (!sema_check_left_right_const(context, left, right)) return false;
 	ArraySize len = 0;
 	bool use_array = true;
 	Type *indexed_type = NULL;
-	if (!sema_analyse_expr(context, left)) return false;
-	if (!sema_cast_const(left)) RETURN_SEMA_ERROR(left, "Expected this to evaluate to a constant value.");
-	if (!sema_analyse_expr(context, right)) return false;
-	if (!sema_cast_const(right)) RETURN_SEMA_ERROR(right, "Expected this to evaluate to a constant value.");
 	Type *element_type = left->type->canonical;
 	Type *right_type = right->type->canonical;
 	switch (left->const_expr.const_kind)
diff --git a/src/compiler/sema_decls.c b/src/compiler/sema_decls.c
index c8b8fe66d..eee889855 100755
--- a/src/compiler/sema_decls.c
+++ b/src/compiler/sema_decls.c
@@ -1802,27 +1802,37 @@ static bool sema_find_typed_operator_in_list(SemaContext *context, Decl **method
 {
 
 	Decl *candidate = *candidate_ref;
+	Type *candidate_type = candidate ? candidate->func_decl.signature.params[1]->type : NULL;
+	bool last_first_arg_exact_match = candidate_type ? candidate_type->canonical == binary_type : false;
+
 	FOREACH(Decl *, func, methods)
 	{
 		if (func->func_decl.operator != operator_overload) continue;
 		if (parent_type && parent_type != typeget(func->func_decl.type_parent)) continue;
 		if ((overload_type & func->func_decl.overload_type) == 0) continue;
+		bool is_exact_match = true;
 		if (!func->func_decl.is_wildcard_overload)
 		{
 			Type *first_arg = func->func_decl.signature.params[1]->type->canonical;
 			if (first_arg != binary_type)
 			{
+				is_exact_match = false;
 				if (!binary_arg) continue;
 				if (!may_cast(context, binary_arg, first_arg, false, true)) continue;
 			}
 		}
 		if (candidate && !candidate->func_decl.is_wildcard_overload)
 		{
+			if (last_first_arg_exact_match && !is_exact_match) continue;
+			if (!last_first_arg_exact_match && is_exact_match) goto MATCH;
+			assert(!last_first_arg_exact_match);
 			*ambiguous_ref = func;
 			*candidate_ref = candidate;
 			return false;
 		}
+MATCH:
 		candidate = func;
+		last_first_arg_exact_match = is_exact_match;
 	}
 	*candidate_ref = candidate;
 	return true;
diff --git a/src/compiler/sema_expr.c b/src/compiler/sema_expr.c
index 391cfb69b..0de6a0b2e 100644
--- a/src/compiler/sema_expr.c
+++ b/src/compiler/sema_expr.c
@@ -1224,6 +1224,50 @@ static inline bool sema_expr_analyse_ct_identifier(SemaContext *context, Expr *e
 }
 
 
+static inline bool sema_binary_analyse_with_inference(SemaContext *context, Expr *left, Expr *right, BinaryOp op)
+{
+	const static int op_table[BINARYOP_LAST + 1] = {
+		[BINARYOP_AND] = 1, [BINARYOP_OR] = 1, [BINARYOP_CT_AND] = 1, [BINARYOP_CT_OR] = 1,
+		[BINARYOP_EQ] = 2, [BINARYOP_NE] = 2 };
+	int op_result = op_table[op];
+	if (op_result == 1) return true;
+	// If lhs or rhs is an initializer list, infer
+	bool is_init_rhs = right->expr_kind == EXPR_INITIALIZER_LIST;
+	bool is_init_lhs = left->expr_kind == EXPR_INITIALIZER_LIST;
+	if (is_init_rhs && is_init_lhs) goto EVAL_BOTH;
+
+	if (is_init_rhs)
+	{
+		if (!sema_analyse_expr(context, left)) return false;
+		if (type_kind_is_any_vector(type_flatten(left->type)->type_kind))
+		{
+			return sema_analyse_inferred_expr(context, left->type, right);
+		}
+		return sema_analyse_expr(context, right);
+	}
+	if (is_init_lhs)
+	{
+		if (!sema_analyse_expr(context, right)) return false;
+		if (type_kind_is_any_vector(type_flatten(right->type)->type_kind))
+		{
+			return sema_analyse_inferred_expr(context, right->type, left);
+		}
+		return sema_analyse_expr(context, left);
+	}
+
+	if (op_result != 2) goto EVAL_BOTH;
+
+	if (!sema_analyse_expr(context, left)) return false;
+	if (left->type->canonical->type_kind == TYPE_ENUM)
+	{
+		return sema_analyse_inferred_expr(context, left->type, right);
+	}
+	return sema_analyse_expr(context, right);
+
+EVAL_BOTH:
+	return sema_analyse_expr(context, left) && sema_analyse_expr(context, right);
+}
+
 static inline bool sema_binary_analyse_subexpr(SemaContext *context, Expr *left, Expr *right)
 {
 	// Special handling of f = FOO_BAR
@@ -1273,7 +1317,8 @@ static inline bool sema_binary_analyse_arithmetic_subexpr(SemaContext *context,
 	Expr *right = exprptr(expr->binary_expr.right);
 
 	// 1. Analyse both sides.
-	if (!sema_binary_analyse_subexpr(context, left, right)) return false;
+	ASSERT_SPAN(expr, left->resolve_status == RESOLVE_DONE);
+	ASSERT_SPAN(expr, right->resolve_status == RESOLVE_DONE);
 
 	Type *left_type = type_no_optional(left->type)->canonical;
 	Type *right_type = type_no_optional(right->type)->canonical;
@@ -8656,10 +8701,22 @@ static inline bool sema_expr_analyse_binary(SemaContext *context, Type *infer_ty
 		RETURN_SEMA_ERROR(expr, "You need to add explicit parentheses to clarify precedence.");
 	}
 	BinaryOp operator = expr->binary_expr.operator;
+	if (operator >= BINARYOP_ASSIGN)
+	{
+		if (left->expr_kind != EXPR_TYPEINFO)
+		{
+			if (!sema_analyse_expr_lvalue(context, left, NULL)) return false;
+		}
+	}
+	else
+	{
+		if (operator == BINARYOP_ELSE) return sema_expr_analyse_or_error(context, expr, left, right, infer_type, failed_ref);
+		if (!sema_binary_analyse_with_inference(context, left, right, operator)) return false;
+	}
 	switch (operator)
 	{
 		case BINARYOP_ELSE:
-			return sema_expr_analyse_or_error(context, expr, left, right, infer_type, failed_ref);
+			UNREACHABLE
 		case BINARYOP_CT_CONCAT:
 			return sema_expr_analyse_ct_concat(context, expr, left, right, failed_ref);
 		case BINARYOP_CT_OR:
diff --git a/src/compiler/sema_internal.h b/src/compiler/sema_internal.h
index 9cd87cbff..bd3776ae9 100644
--- a/src/compiler/sema_internal.h
+++ b/src/compiler/sema_internal.h
@@ -130,6 +130,12 @@ INLINE bool sema_set_alloca_alignment(SemaContext *context, Type *type, AlignSiz
 INLINE void sema_display_deprecated_warning_on_use(Decl *decl, SourceSpan span);
 bool sema_expr_analyse_ct_concat(SemaContext *context, Expr *concat_expr, Expr *left, Expr *right, bool *failed_ref);
 
+INLINE bool sema_check_left_right_const(SemaContext *context, Expr *left, Expr *right)
+{
+	if (!sema_cast_const(left)) RETURN_SEMA_ERROR(left, "Expected this to evaluate to a constant value.");
+	if (!sema_cast_const(right)) RETURN_SEMA_ERROR(right, "Expected this to evaluate to a constant value.");
+	return true;
+}
 
 INLINE bool sema_set_abi_alignment(SemaContext *context, Type *type, AlignSize *result)
 {
diff --git a/test/test_suite/methods/overload_method_example.c3t b/test/test_suite/methods/overload_method_example.c3t
new file mode 100644
index 000000000..629d32ee2
--- /dev/null
+++ b/test/test_suite/methods/overload_method_example.c3t
@@ -0,0 +1,39 @@
+// #target: macos-x64
+module test;
+struct Word {int x;}
+typedef Byte = inline ushort;
+
+macro Word Word.add0(self, int other) @operator(+) => { self.x + (int)other };
+macro Word Word.add1(self, Byte other) @operator(+) => { self.x + (int)other };
+
+fn int main()
+{
+	Word a = {1};
+	Byte b = 2;
+	Word c = a + b;
+	return 0;
+}
+
+/* #expect: test.ll
+
+define i32 @main() #0 {
+entry:
+  %a = alloca %Word, align 4
+  %b = alloca i16, align 2
+  %c = alloca %Word, align 4
+  %self = alloca %Word, align 4
+  %other = alloca i16, align 2
+  %literal = alloca %Word, align 4
+  call void @llvm.memcpy.p0.p0.i32(ptr align 4 %a, ptr align 4 @.__const, i32 4, i1 false)
+  store i16 2, ptr %b, align 2
+  call void @llvm.memcpy.p0.p0.i32(ptr align 4 %self, ptr align 4 %a, i32 4, i1 false)
+  %0 = load i16, ptr %b, align 2
+  store i16 %0, ptr %other, align 2
+  %1 = load i32, ptr %self, align 4
+  %2 = load i16, ptr %other, align 2
+  %zext = zext i16 %2 to i32
+  %add = add i32 %1, %zext
+  store i32 %add, ptr %literal, align 4
+  call void @llvm.memcpy.p0.p0.i32(ptr align 4 %c, ptr align 4 %literal, i32 4, i1 false)
+  ret i32 0
+}