diff --git a/lru/lru_with_expiry_test.go b/lru/lru_with_expiry_test.go
index 42812d70..64190859 100644
--- a/lru/lru_with_expiry_test.go
+++ b/lru/lru_with_expiry_test.go
@@ -45,6 +45,11 @@ func TestTypedGetWithExpiry(t *testing.T) {
 		{name: "string_hit_expiring_big_jump", keyToAdd: "myKey", keyToGet: "myKey", keyExpiry: startTime.Add(time.Hour), setTime: startTime.Add(time.Hour * 24 * 365), expectedOK: false},
 		{name: "string_hit_expiring_exact_jump", keyToAdd: "myKey", keyToGet: "myKey", keyExpiry: startTime.Add(time.Hour), setTime: startTime.Add(time.Hour), expectedOK: false},
 		{name: "string_hit_expiring_jump_just_under", keyToAdd: "myKey", keyToGet: "myKey", keyExpiry: startTime.Add(time.Hour), setTime: startTime.Add(time.Hour - time.Nanosecond), expectedOK: true},
+		{name: "string_hit_zero_val_no_advance_prior_entry", keyToAdd: "fizzlebat", keyToGet: "fizzlebat", setTime: startTime, expectedOK: true},
+		{name: "string_hit_zero_val_big_jump_prior_entry", keyToAdd: "fizzlebat", keyToGet: "fizzlebat", setTime: startTime.Add(time.Hour * 24 * 365), expectedOK: true},
+		{name: "string_hit_expiring_big_jump_prior_entry", keyToAdd: "fizzlebat", keyToGet: "fizzlebat", keyExpiry: startTime.Add(time.Hour), setTime: startTime.Add(time.Hour * 24 * 365), expectedOK: false},
+		{name: "string_hit_expiring_exact_jump_prior_entry", keyToAdd: "fizzlebat", keyToGet: "fizzlebat", keyExpiry: startTime.Add(time.Hour), setTime: startTime.Add(time.Hour), expectedOK: false},
+		{name: "string_hit_expiring_jump_just_under_prior_entry", keyToAdd: "fizzlebat", keyToGet: "fizzlebat", keyExpiry: startTime.Add(time.Hour), setTime: startTime.Add(time.Hour - time.Nanosecond), expectedOK: true},
 	}
 
 	for _, tt := range getTests {
@@ -52,6 +57,8 @@ func TestTypedGetWithExpiry(t *testing.T) {
 			clk := fake.NewClock(startTime)
 			lru := TypedNew[string, int](0)
 			lru.Clock = clk
+			// add a pre-existing value that we can update with a different expiry
+			lru.AddExpiring("fizzlebat", 4321, startTime.Add(time.Minute))
 			lru.AddExpiring(tt.keyToAdd, 1234, tt.keyExpiry)
 
 			clk.SetClock(tt.setTime)
diff --git a/lru/typed_lru.go b/lru/typed_lru.go
index 163c766a..57eb3de3 100644
--- a/lru/typed_lru.go
+++ b/lru/typed_lru.go
@@ -121,8 +121,19 @@ func (c *TypedCache[K, V]) AddExpiring(key K, value V, expiration time.Time) {
 	if ele, hit := c.cache[key]; hit {
 		c.ll.MoveToFront(ele)
 		ele.value.value = value
+		// Remove the existing expiration handle from the heap before (possibly) adding a new one.
+		// this way we don't end up with both expirations in the heap.
+		if ele.value.hasExpiry {
+			c.expirations.Remove(ele.value.expHandle)
+		}
 		if !expiration.IsZero() {
 			ele.value.expHandle = c.expirations.Push(expiration, weak.Make(ele))
+			ele.value.hasExpiry = true
+			ele.value.expiry = expiration.Sub(c.expiryBase)
+		} else {
+			ele.value.expHandle = nil
+			ele.value.hasExpiry = false
+			ele.value.expiry = 0
 		}
 		return
 	}