diff --git a/src/operands.rs b/src/operands.rs
index 8756ae0..078a392 100644
--- a/src/operands.rs
+++ b/src/operands.rs
@@ -27,6 +27,41 @@ pub enum ImmediateOperand {
 }
 
 impl ImmediateOperand {
+    // Sign-extend [`Self::Byte`] into [`Self::Word`].
+    // Returns [`Self::Word`], if already a word.
+    pub fn sign_extend(self) -> Self {
+        match self {
+            Self::Byte(_) => {
+                let sign = self.msb();
+                let byte = self.flip_sign();
+                let word = byte.as_word();
+                if sign {
+                    return word.flip_sign();
+                } else {
+                    return word;
+                }
+            }
+            Self::Word(_) => self,
+        }
+    }
+
+    // Interprets [`Self::Byte`] as [`Self::Word`].
+    // Returns word, if already a [`Self::Word`].
+    pub fn as_word(self) -> Self {
+        match self {
+            Self::Byte(b) => Self::Word(b as Word),
+            Self::Word(_) => self,
+        }
+    }
+
+    // Flip most significant bit.
+    pub fn flip_sign(self) -> Self {
+        match self {
+            Self::Byte(b) => Self::Byte(b ^ (1 << 7)),
+            Self::Word(w) => Self::Word(w ^ (1 << 15)),
+        }
+    }
+
     // Check if value is zero.
     pub fn zero(&self) -> bool {
         match self {
@@ -47,7 +82,7 @@ impl ImmediateOperand {
     }
 
     /// Check if least significant bit is set.
-    pub fn lsb(&self) -> bool {
+    pub fn _lsb(&self) -> bool {
         match self {
             Self::Byte(byte) => return byte & 1 == 1,
             Self::Word(word) => return word & 1 == 1,
@@ -57,8 +92,8 @@ impl ImmediateOperand {
     /// Check if most significant bit is set.
     pub fn msb(&self) -> bool {
         match self {
-            Self::Byte(byte) => return byte & (1 << 3) == 1,
-            Self::Word(word) => return word & (1 << 7) == 1,
+            Self::Byte(byte) => return (byte >> 7) == 1,
+            Self::Word(word) => return (word >> 15) == 1,
         }
     }
 }
@@ -74,8 +109,11 @@ impl Add for ImmediateOperand {
             },
             ImmediateOperand::Word(lhsw) => match other {
                 ImmediateOperand::Word(rhsw) => ImmediateOperand::Word(lhsw.wrapping_add(rhsw)),
-                ImmediateOperand::Byte(rhsb) => {
-                    ImmediateOperand::Word(lhsw.wrapping_add(rhsb as Word))
+                ImmediateOperand::Byte(_) => {
+                    ImmediateOperand::Word(lhsw.wrapping_add(match other.sign_extend() {
+                        ImmediateOperand::Word(w) => w,
+                        _ => panic!("Sign-extended Word is a Byte"),
+                    }))
                 }
             },
         }
@@ -118,8 +156,11 @@ impl Sub for ImmediateOperand {
             },
             ImmediateOperand::Word(lhsw) => match other {
                 ImmediateOperand::Word(rhsw) => ImmediateOperand::Word(lhsw.wrapping_sub(rhsw)),
-                ImmediateOperand::Byte(rhsb) => {
-                    ImmediateOperand::Word(lhsw.wrapping_sub(rhsb as Word))
+                ImmediateOperand::Byte(_) => {
+                    ImmediateOperand::Word(lhsw.wrapping_sub(match other.sign_extend() {
+                        ImmediateOperand::Word(w) => w,
+                        _ => panic!("Sign-extended Word is a Byte"),
+                    }))
                 }
             },
         }
@@ -137,8 +178,11 @@ impl Mul for ImmediateOperand {
             },
             ImmediateOperand::Word(lhsw) => match other {
                 ImmediateOperand::Word(rhsw) => ImmediateOperand::Word(lhsw.wrapping_mul(rhsw)),
-                ImmediateOperand::Byte(rhsb) => {
-                    ImmediateOperand::Word(lhsw.wrapping_mul(rhsb as Word))
+                ImmediateOperand::Byte(_) => {
+                    ImmediateOperand::Word(lhsw.wrapping_mul(match other.sign_extend() {
+                        ImmediateOperand::Word(w) => w,
+                        _ => panic!("Sign-extended Word is a Byte"),
+                    }))
                 }
             },
         }
@@ -156,8 +200,11 @@ impl Div for ImmediateOperand {
             },
             ImmediateOperand::Word(lhsw) => match other {
                 ImmediateOperand::Word(rhsw) => ImmediateOperand::Word(lhsw.wrapping_div(rhsw)),
-                ImmediateOperand::Byte(rhsb) => {
-                    ImmediateOperand::Word(lhsw.wrapping_div(rhsb as Word))
+                ImmediateOperand::Byte(_) => {
+                    ImmediateOperand::Word(lhsw.wrapping_div(match other.sign_extend() {
+                        ImmediateOperand::Word(w) => w,
+                        _ => panic!("Sign-extended Word is a Byte"),
+                    }))
                 }
             },
         }
@@ -339,3 +386,53 @@ impl std::fmt::Display for Pointer32 {
         write!(f, "{:#04x}:{:#04x}", self.segment, self.offset)
     }
 }
+
+#[cfg(test)]
+mod tests {
+    use super::*;
+
+    #[test]
+    fn test_msb() {
+        let pos = ImmediateOperand::Byte(1 << 4);
+        let neg = ImmediateOperand::Byte(1 << 7);
+        assert_eq!(pos.msb(), false);
+        assert_eq!(neg.msb(), true);
+    }
+
+    #[test]
+    fn test_as_word() {
+        let b: u8 = 5;
+        let byte = ImmediateOperand::Byte(b);
+        let word = ImmediateOperand::Word(b as Word);
+        assert_eq!(byte.as_word(), word);
+        assert_eq!(word, word);
+    }
+
+    #[test]
+    fn test_flip_sign_neg_to_pos() {
+        let b = 0 << 2;
+        let byte = ImmediateOperand::Byte((1 << 7) | b);
+        let word = ImmediateOperand::Word((1 << 15) | b as Word);
+        assert_eq!(byte.flip_sign(), ImmediateOperand::Byte(b));
+        assert_eq!(word.flip_sign(), ImmediateOperand::Word(b as Word));
+    }
+
+    #[test]
+    fn test_flip_sign_pos_to_neg() {
+        let b = 1 << 2;
+        let byte = ImmediateOperand::Byte(b);
+        let word = ImmediateOperand::Word(b as Word);
+        assert_eq!(byte.flip_sign(), ImmediateOperand::Byte((1 << 7) | b));
+        assert_eq!(
+            word.flip_sign(),
+            ImmediateOperand::Word((1 << 15) | b as Word)
+        );
+    }
+
+    #[test]
+    fn test_sign_extend() {
+        let byte = ImmediateOperand::Byte(1 << 7);
+        let word = ImmediateOperand::Word(1 << 15);
+        assert_eq!(byte.sign_extend(), word);
+    }
+}