diff --git a/kotlin/codegen/src/main/java/com/squareup/moshi/kotlin/codegen/metadata.kt b/kotlin/codegen/src/main/java/com/squareup/moshi/kotlin/codegen/metadata.kt
index 32d579f..1f4e9ac 100644
--- a/kotlin/codegen/src/main/java/com/squareup/moshi/kotlin/codegen/metadata.kt
+++ b/kotlin/codegen/src/main/java/com/squareup/moshi/kotlin/codegen/metadata.kt
@@ -52,6 +52,7 @@ import java.lang.annotation.ElementType
 import java.lang.annotation.Retention
 import java.lang.annotation.RetentionPolicy
 import java.lang.annotation.Target
+import java.util.TreeSet
 import javax.annotation.processing.Messager
 import javax.lang.model.element.ElementKind
 import javax.lang.model.element.TypeElement
@@ -322,10 +323,22 @@ private fun String.escapeDollarSigns(): String {
 private fun TypeName.unwrapTypeAlias(): TypeName {
   return when (this) {
     is ClassName -> {
-      tag<TypeNameAliasTag>()?.type?.unwrapTypeAlias() ?: this
+      tag<TypeNameAliasTag>()?.type?.let { unwrappedType ->
+        // If any type is nullable, then the whole thing is nullable
+        var isAnyNullable = isNullable
+        // Keep track of all annotations across type levels. Sort them too for consistency.
+        val runningAnnotations = TreeSet<AnnotationSpec>(compareBy { it.toString() }).apply {
+          addAll(annotations)
+        }
+        val nestedUnwrappedType = unwrappedType.unwrapTypeAlias()
+        runningAnnotations.addAll(nestedUnwrappedType.annotations)
+        isAnyNullable = isAnyNullable || nestedUnwrappedType.isNullable
+        nestedUnwrappedType.copy(nullable = isAnyNullable, annotations = runningAnnotations.toList())
+      } ?: this
     }
     is ParameterizedTypeName -> {
       return (rawType.unwrapTypeAlias() as ClassName).parameterizedBy(typeArguments.map { it.unwrapTypeAlias() })
+          .copy(nullable = isNullable, annotations = annotations)
     }
     is TypeVariableName -> {
       return copy(bounds = bounds.map { it.unwrapTypeAlias() })
diff --git a/kotlin/tests/src/test/kotlin/com/squareup/moshi/kotlin/DualKotlinTest.kt b/kotlin/tests/src/test/kotlin/com/squareup/moshi/kotlin/DualKotlinTest.kt
index 8017ed9..05dd50a 100644
--- a/kotlin/tests/src/test/kotlin/com/squareup/moshi/kotlin/DualKotlinTest.kt
+++ b/kotlin/tests/src/test/kotlin/com/squareup/moshi/kotlin/DualKotlinTest.kt
@@ -433,7 +433,7 @@ class DualKotlinTest(useReflection: Boolean) {
       val parameterized: GenericClass<TypeAlias>,
       val wildcardIn: GenericClass<in TypeAlias>,
       val wildcardOut: GenericClass<out TypeAlias>,
-      val complex: GenericClass<GenericTypeAlias>
+      val complex: GenericClass<GenericTypeAlias>?
   )
 
   // Regression test for https://github.com/square/moshi/issues/991
@@ -481,11 +481,52 @@ class DualKotlinTest(useReflection: Boolean) {
       val double: Double,
       val nullableDouble: Double? = null
   )
+
+  // Regression test for https://github.com/square/moshi/issues/990
+  @Test fun nullableProperties() {
+    val adapter = moshi.adapter<NullableList>()
+
+    @Language("JSON")
+    val testJson = """{"nullableList":null}"""
+
+    assertThat(adapter.serializeNulls().toJson(NullableList(null)))
+        .isEqualTo(testJson)
+
+    val result = adapter.fromJson(testJson)!!
+    assertThat(result.nullableList).isNull()
+  }
+
+  @JsonClass(generateAdapter = true)
+  data class NullableList(val nullableList: List<Any>?)
+
+  @Test fun typeAliasNullability() {
+    val adapter = moshi.adapter<TypeAliasNullability>()
+
+    @Language("JSON")
+    val testJson = """{"aShouldBeNonNull":3,"nullableAShouldBeNullable":null,"redundantNullableAShouldBeNullable":null,"manuallyNullableAShouldBeNullable":null,"convolutedMultiNullableShouldBeNullable":null,"deepNestedNullableShouldBeNullable":null}"""
+
+    val instance = TypeAliasNullability(3, null, null, null, null, null)
+    assertThat(adapter.serializeNulls().toJson(instance))
+        .isEqualTo(testJson)
+
+    val result = adapter.fromJson(testJson)!!
+    assertThat(result).isEqualTo(instance)
+  }
+
+  @JsonClass(generateAdapter = true)
+  data class TypeAliasNullability(
+      val aShouldBeNonNull: A,
+      val nullableAShouldBeNullable: NullableA,
+      val redundantNullableAShouldBeNullable: NullableA?,
+      val manuallyNullableAShouldBeNullable: A?,
+      val convolutedMultiNullableShouldBeNullable: NullableB?,
+      val deepNestedNullableShouldBeNullable: E
+  )
 }
 
 typealias TypeAlias = Int
 @Suppress("REDUNDANT_PROJECTION")
-typealias GenericTypeAlias = List<out GenericClass<in TypeAlias>>
+typealias GenericTypeAlias = List<out GenericClass<in TypeAlias>?>?
 
 @JsonClass(generateAdapter = true)
 data class GenericClass<T>(val value: T)
@@ -493,3 +534,11 @@ data class GenericClass<T>(val value: T)
 // Has to be outside since inline classes are only allowed on top level
 @JsonClass(generateAdapter = true)
 inline class InlineClass(val i: Int)
+
+typealias A = Int
+typealias NullableA = A?
+typealias B = NullableA
+typealias NullableB = B?
+typealias C = NullableA
+typealias D = C
+typealias E = D