diff --git a/src/compiler/llvm_codegen_expr.c b/src/compiler/llvm_codegen_expr.c
index 4ecb22116..9051a171a 100644
--- a/src/compiler/llvm_codegen_expr.c
+++ b/src/compiler/llvm_codegen_expr.c
@@ -1300,7 +1300,7 @@ void llvm_emit_cast(GenContext *c, CastKind cast_kind, BEValue *value, Type *to_
 			llvm_value_rvalue(c, value);
 			value->value = type_convert_will_trunc(to_type, from_type)
 			       ? LLVMBuildTrunc(c->builder, value->value, llvm_get_type(c, to_type), "siuitrunc")
-			       : LLVMBuildZExt(c->builder, value->value, llvm_get_type(c, to_type), "siuiext");
+			       : LLVMBuildSExt(c->builder, value->value, llvm_get_type(c, to_type), "siuiext");
 			break;
 		case CAST_SIFP:
 			llvm_value_rvalue(c, value);
diff --git a/src/compiler/sema_casts.c b/src/compiler/sema_casts.c
index 6cfd83fe3..f7cb1a092 100644
--- a/src/compiler/sema_casts.c
+++ b/src/compiler/sema_casts.c
@@ -245,6 +245,13 @@ bool lit_integer_to_enum(Expr *expr, Type *canonical, Type *type)
 
 static bool int_conversion(Expr *expr, CastKind kind, Type *canonical, Type *type)
 {
+	// Fold pointer casts if narrowing
+	if (expr->expr_kind == EXPR_CAST && expr->cast_expr.kind == CAST_PTRXI
+	    && type_size(type) <= type_size(expr->type))
+	{
+		expr->type = type;
+		return true;
+	}
 	if (insert_runtime_cast_unless_const(expr, kind, type)) return true;
 
 	expr->const_expr.ixx = int_conv(expr->const_expr.ixx, canonical->type_kind);
diff --git a/test/test_suite/cast/cast_from_ptr.c3t b/test/test_suite/cast/cast_from_ptr.c3t
new file mode 100644
index 000000000..5fd784a32
--- /dev/null
+++ b/test/test_suite/cast/cast_from_ptr.c3t
@@ -0,0 +1,18 @@
+module test;
+
+fn void tester()
+{
+    int *x;
+    short y = (short)((uptr)(x));
+    uptr z = (uptr)((short)((uptr)(x)));
+}
+
+/* #expect: test.ll
+
+  %0 = load i32*, i32** %x, align 8
+  %ptrxi = ptrtoint i32* %0 to i16
+  store i16 %ptrxi, i16* %y, align 2
+  %1 = load i32*, i32** %x, align 8
+  %ptrxi1 = ptrtoint i32* %1 to i16
+  %siuiext = sext i16 %ptrxi1 to i64
+  store i64 %siuiext, i64* %z, align 8
diff --git a/test/test_suite/clang/2002-01_02.c3t b/test/test_suite/clang/2002-01_02.c3t
index 134cb61e5..fc6e621f7 100644
--- a/test/test_suite/clang/2002-01_02.c3t
+++ b/test/test_suite/clang/2002-01_02.c3t
@@ -234,9 +234,8 @@ if.then:                                          ; preds = %loop.body
   %3 = load %Edge_rec*, %Edge_rec** %basel, align 8
   %4 = getelementptr inbounds %Edge_rec, %Edge_rec* %3, i32 0, i32 1
   %5 = load %Edge_rec*, %Edge_rec** %4, align 8
-  %ptrxi = ptrtoint %Edge_rec* %5 to i64
-  %sisitrunc = trunc i64 %ptrxi to i32
-  ret i32 %sisitrunc
+  %ptrxi = ptrtoint %Edge_rec* %5 to i32
+  ret i32 %ptrxi
 
 if.exit:                                          ; preds = %loop.body
   br label %loop.body
diff --git a/test/test_suite/functions/test_regression.c3t b/test/test_suite/functions/test_regression.c3t
index 265e1b4a1..f728773d8 100644
--- a/test/test_suite/functions/test_regression.c3t
+++ b/test/test_suite/functions/test_regression.c3t
@@ -476,7 +476,7 @@ loop.cond:                                        ; preds = %loop.body, %entry
 loop.body:                                        ; preds = %loop.cond
   %6 = load i32, i32* %i, align 4
   %7 = load i32, i32* %i, align 4
-  %siuiext = zext i32 %7 to i64
+  %siuiext = sext i32 %7 to i64
   %8 = call i32 @"std::array::linkedlist.int.LinkedList__get"(%LinkedList* %list, i64 %siuiext)
   %9 = call i32 (i8*, ...) @printf(i8* getelementptr inbounds ([17 x i8], [17 x i8]* @.str.2, i32 0, i32 0), i32 %6, i32 %8)
   %10 = load i32, i32* %i, align 4
@@ -511,7 +511,7 @@ loop.cond2:                                       ; preds = %loop.body5, %loop.e
 loop.body5:                                       ; preds = %loop.cond2
   %16 = load i32, i32* %i1, align 4
   %17 = load i32, i32* %i1, align 4
-  %siuiext6 = zext i32 %17 to i64
+  %siuiext6 = sext i32 %17 to i64
   %18 = call i32 @"std::array::list.int.List__get"(%List* %array, i64 %siuiext6)
   %19 = call i32 (i8*, ...) @printf(i8* getelementptr inbounds ([17 x i8], [17 x i8]* @.str.5, i32 0, i32 0), i32 %16, i32 %18)
   %20 = load i32, i32* %i1, align 4
diff --git a/test/test_suite/functions/test_regression_mingw.c3t b/test/test_suite/functions/test_regression_mingw.c3t
index 7b7ae7959..36059aa20 100644
--- a/test/test_suite/functions/test_regression_mingw.c3t
+++ b/test/test_suite/functions/test_regression_mingw.c3t
@@ -538,7 +538,7 @@ loop.cond:                                        ; preds = %loop.body, %entry
 loop.body:                                        ; preds = %loop.cond
   %6 = load i32, i32* %i, align 4
   %7 = load i32, i32* %i, align 4
-  %siuiext = zext i32 %7 to i64
+  %siuiext = sext i32 %7 to i64
   %8 = call i32 @"std::array::linkedlist.int.LinkedList__get"(%LinkedList* %list, i64 %siuiext)
   %9 = call i32 (i8*, ...) @printf(i8* getelementptr inbounds ([17 x i8], [17 x i8]* @.str.2, i32 0, i32 0), i32 %6, i32 %8)
   %10 = load i32, i32* %i, align 4
@@ -573,7 +573,7 @@ loop.cond2:                                       ; preds = %loop.body5, %loop.e
 loop.body5:                                       ; preds = %loop.cond2
   %16 = load i32, i32* %i1, align 4
   %17 = load i32, i32* %i1, align 4
-  %siuiext6 = zext i32 %17 to i64
+  %siuiext6 = sext i32 %17 to i64
   %18 = call i32 @"std::array::list.int.List__get"(%List* %array, i64 %siuiext6)
   %19 = call i32 (i8*, ...) @printf(i8* getelementptr inbounds ([17 x i8], [17 x i8]* @.str.5, i32 0, i32 0), i32 %16, i32 %18)
   %20 = load i32, i32* %i1, align 4