diff --git a/test/libsolidity/semanticTests/userDefinedValueType/dirty_uint8_read.sol b/test/libsolidity/semanticTests/userDefinedValueType/dirty_uint8_read.sol
new file mode 100644
index 000000000..4100e17f8
--- /dev/null
+++ b/test/libsolidity/semanticTests/userDefinedValueType/dirty_uint8_read.sol
@@ -0,0 +1,26 @@
+type MyInt8 is int8;
+contract C {
+    MyInt8 public x = MyInt8.wrap(-5);
+
+    /// The most significant bit is flipped to 0
+    function create_dirty_slot() external {
+        uint mask  = 2**255 -1;
+        assembly {
+            let value := sload(x.slot)
+            sstore(x.slot, and(mask, value))
+        }
+    }
+
+    function read_unclean_value() external returns (bytes32 ret) {
+        MyInt8 value = x;
+        assembly {
+            ret := value
+        }
+    }
+}
+// ====
+// compileViaYul: also
+// ----
+// x() -> -5
+// create_dirty_slot() ->
+// read_unclean_value() -> 0xfffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffb
diff --git a/test/libsolidity/semanticTests/userDefinedValueType/immutable_signed.sol b/test/libsolidity/semanticTests/userDefinedValueType/immutable_signed.sol
new file mode 100644
index 000000000..8923984a4
--- /dev/null
+++ b/test/libsolidity/semanticTests/userDefinedValueType/immutable_signed.sol
@@ -0,0 +1,21 @@
+type MyInt is int16;
+type MyBytes is bytes2;
+contract C {
+    MyInt immutable a = MyInt.wrap(-2);
+    MyBytes immutable b = MyBytes.wrap("ab");
+    function() internal returns (uint) immutable f = g;
+    function direct() view external returns (MyInt, MyBytes) {
+        return (a, b);
+    }
+    function viaasm() view external returns (bytes32 x, bytes32 y) {
+        MyInt _a = a;
+        MyBytes _b = b;
+        assembly { x := _a y := _b }
+    }
+    function g() internal pure returns (uint) { return 2; }
+}
+// ====
+// compileViaYul: also
+// ----
+// direct() -> -2, 0x6162000000000000000000000000000000000000000000000000000000000000
+// viaasm() -> 0xfffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffe, 0x6162000000000000000000000000000000000000000000000000000000000000
diff --git a/test/libsolidity/semanticTests/userDefinedValueType/storage_signed.sol b/test/libsolidity/semanticTests/userDefinedValueType/storage_signed.sol
new file mode 100644
index 000000000..80745866a
--- /dev/null
+++ b/test/libsolidity/semanticTests/userDefinedValueType/storage_signed.sol
@@ -0,0 +1,35 @@
+type MyInt is int16;
+contract C {
+    bytes2 first = "ab";
+    MyInt public a = MyInt.wrap(-2);
+    bytes2 third = "ef";
+    function direct() external returns (MyInt) {
+        return a;
+    }
+    function indirect() external returns (int16) {
+        return MyInt.unwrap(a);
+    }
+    function toMemDirect() external returns (MyInt[1] memory) {
+        return [a];
+    }
+    function toMemIndirect() external returns (int16[1] memory) {
+        return [MyInt.unwrap(a)];
+    }
+    function div() external returns (int16) {
+        return MyInt.unwrap(a) / 2;
+    }
+    function viaasm() external returns (bytes32 x) {
+        MyInt st = a;
+        assembly { x := st }
+    }
+}
+// ====
+// compileViaYul: also
+// ----
+// a() -> -2
+// direct() -> -2
+// indirect() -> -2
+// toMemDirect() -> -2
+// toMemIndirect() -> -2
+// div() -> -1
+// viaasm() -> 0xfffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffe