diff --git a/src/compiler/checker.ts b/src/compiler/checker.ts
index b764348cc6f10..c9ba83b15b9e4 100644
--- a/src/compiler/checker.ts
+++ b/src/compiler/checker.ts
@@ -18791,10 +18791,11 @@ namespace ts {
                         // type references (which are intended by be compared structurally). Obtain the variance
                         // information for the type parameters and relate the type arguments accordingly.
                         const variances = getVariances((source as TypeReference).target);
-                        // We return Ternary.Maybe for a recursive invocation of getVariances (signalled by emptyArray). This
+                        // We return Ternary.Unknown for a recursive invocation of getVariances (signalled by emptyArray). This
                         // effectively means we measure variance only from type parameter occurrences that aren't nested in
                         // recursive instantiations of the generic type.
                         if (variances === emptyArray) {
+                            outofbandVarianceMarkerHandler!(/*onlyUnreliable*/ false);
                             return Ternary.Unknown;
                         }
                         const varianceResult = relateVariances(getTypeArguments(source as TypeReference), getTypeArguments(target as TypeReference), variances, intersectionState);
@@ -19756,7 +19757,7 @@ namespace ts {
                     outofbandVarianceMarkerHandler = oldHandler;
                     if (unmeasurable || unreliable) {
                         if (unmeasurable) {
-                            variance |= VarianceFlags.Unmeasurable;
+                            variance = VarianceFlags.Unmeasurable;
                         }
                         if (unreliable) {
                             variance |= VarianceFlags.Unreliable;
diff --git a/tests/baselines/reference/checkOrderDependenceGenericAssignability.errors.txt b/tests/baselines/reference/checkOrderDependenceGenericAssignability.errors.txt
new file mode 100644
index 0000000000000..c3b30a5f9aaab
--- /dev/null
+++ b/tests/baselines/reference/checkOrderDependenceGenericAssignability.errors.txt
@@ -0,0 +1,35 @@
+tests/cases/compiler/checkOrderDependenceGenericAssignability.ts(24,7): error TS2322: Type 'Parent<unknown>' is not assignable to type 'Parent<string>'.
+  The types of 'child.a' are incompatible between these types.
+    Type 'unknown' is not assignable to type 'string'.
+
+
+==== tests/cases/compiler/checkOrderDependenceGenericAssignability.ts (1 errors) ====
+    // #44572
+    
+    interface Parent<A> {
+      child: Child<A> | null;
+      parent: Parent<A> | null;
+    }
+    
+    interface Child<A, B = unknown> extends Parent<A> {
+      readonly a: A;
+      // This field isn't necessary to the repro, but the
+      // type parameter is, so including it
+      readonly b: B;
+    }
+    
+    function fn<A>(inp: Child<A>) {
+      // This assignability check defeats the later one
+      const a: Child<unknown> = inp;
+    }
+    
+    // Allowed initialization of pu
+    const pu: Parent<unknown> = { child: { a: 0, b: 0, child: null, parent: null }, parent: null };
+    
+    // Should error
+    const notString: Parent<string> = pu;
+          ~~~~~~~~~
+!!! error TS2322: Type 'Parent<unknown>' is not assignable to type 'Parent<string>'.
+!!! error TS2322:   The types of 'child.a' are incompatible between these types.
+!!! error TS2322:     Type 'unknown' is not assignable to type 'string'.
+    
\ No newline at end of file
diff --git a/tests/baselines/reference/checkOrderDependenceGenericAssignability.js b/tests/baselines/reference/checkOrderDependenceGenericAssignability.js
new file mode 100644
index 0000000000000..4dcb50ee44408
--- /dev/null
+++ b/tests/baselines/reference/checkOrderDependenceGenericAssignability.js
@@ -0,0 +1,37 @@
+//// [checkOrderDependenceGenericAssignability.ts]
+// #44572
+
+interface Parent<A> {
+  child: Child<A> | null;
+  parent: Parent<A> | null;
+}
+
+interface Child<A, B = unknown> extends Parent<A> {
+  readonly a: A;
+  // This field isn't necessary to the repro, but the
+  // type parameter is, so including it
+  readonly b: B;
+}
+
+function fn<A>(inp: Child<A>) {
+  // This assignability check defeats the later one
+  const a: Child<unknown> = inp;
+}
+
+// Allowed initialization of pu
+const pu: Parent<unknown> = { child: { a: 0, b: 0, child: null, parent: null }, parent: null };
+
+// Should error
+const notString: Parent<string> = pu;
+
+
+//// [checkOrderDependenceGenericAssignability.js]
+// #44572
+function fn(inp) {
+    // This assignability check defeats the later one
+    var a = inp;
+}
+// Allowed initialization of pu
+var pu = { child: { a: 0, b: 0, child: null, parent: null }, parent: null };
+// Should error
+var notString = pu;
diff --git a/tests/baselines/reference/checkOrderDependenceGenericAssignability.symbols b/tests/baselines/reference/checkOrderDependenceGenericAssignability.symbols
new file mode 100644
index 0000000000000..ad9be4689614f
--- /dev/null
+++ b/tests/baselines/reference/checkOrderDependenceGenericAssignability.symbols
@@ -0,0 +1,67 @@
+=== tests/cases/compiler/checkOrderDependenceGenericAssignability.ts ===
+// #44572
+
+interface Parent<A> {
+>Parent : Symbol(Parent, Decl(checkOrderDependenceGenericAssignability.ts, 0, 0))
+>A : Symbol(A, Decl(checkOrderDependenceGenericAssignability.ts, 2, 17))
+
+  child: Child<A> | null;
+>child : Symbol(Parent.child, Decl(checkOrderDependenceGenericAssignability.ts, 2, 21))
+>Child : Symbol(Child, Decl(checkOrderDependenceGenericAssignability.ts, 5, 1))
+>A : Symbol(A, Decl(checkOrderDependenceGenericAssignability.ts, 2, 17))
+
+  parent: Parent<A> | null;
+>parent : Symbol(Parent.parent, Decl(checkOrderDependenceGenericAssignability.ts, 3, 25))
+>Parent : Symbol(Parent, Decl(checkOrderDependenceGenericAssignability.ts, 0, 0))
+>A : Symbol(A, Decl(checkOrderDependenceGenericAssignability.ts, 2, 17))
+}
+
+interface Child<A, B = unknown> extends Parent<A> {
+>Child : Symbol(Child, Decl(checkOrderDependenceGenericAssignability.ts, 5, 1))
+>A : Symbol(A, Decl(checkOrderDependenceGenericAssignability.ts, 7, 16))
+>B : Symbol(B, Decl(checkOrderDependenceGenericAssignability.ts, 7, 18))
+>Parent : Symbol(Parent, Decl(checkOrderDependenceGenericAssignability.ts, 0, 0))
+>A : Symbol(A, Decl(checkOrderDependenceGenericAssignability.ts, 7, 16))
+
+  readonly a: A;
+>a : Symbol(Child.a, Decl(checkOrderDependenceGenericAssignability.ts, 7, 51))
+>A : Symbol(A, Decl(checkOrderDependenceGenericAssignability.ts, 7, 16))
+
+  // This field isn't necessary to the repro, but the
+  // type parameter is, so including it
+  readonly b: B;
+>b : Symbol(Child.b, Decl(checkOrderDependenceGenericAssignability.ts, 8, 16))
+>B : Symbol(B, Decl(checkOrderDependenceGenericAssignability.ts, 7, 18))
+}
+
+function fn<A>(inp: Child<A>) {
+>fn : Symbol(fn, Decl(checkOrderDependenceGenericAssignability.ts, 12, 1))
+>A : Symbol(A, Decl(checkOrderDependenceGenericAssignability.ts, 14, 12))
+>inp : Symbol(inp, Decl(checkOrderDependenceGenericAssignability.ts, 14, 15))
+>Child : Symbol(Child, Decl(checkOrderDependenceGenericAssignability.ts, 5, 1))
+>A : Symbol(A, Decl(checkOrderDependenceGenericAssignability.ts, 14, 12))
+
+  // This assignability check defeats the later one
+  const a: Child<unknown> = inp;
+>a : Symbol(a, Decl(checkOrderDependenceGenericAssignability.ts, 16, 7))
+>Child : Symbol(Child, Decl(checkOrderDependenceGenericAssignability.ts, 5, 1))
+>inp : Symbol(inp, Decl(checkOrderDependenceGenericAssignability.ts, 14, 15))
+}
+
+// Allowed initialization of pu
+const pu: Parent<unknown> = { child: { a: 0, b: 0, child: null, parent: null }, parent: null };
+>pu : Symbol(pu, Decl(checkOrderDependenceGenericAssignability.ts, 20, 5))
+>Parent : Symbol(Parent, Decl(checkOrderDependenceGenericAssignability.ts, 0, 0))
+>child : Symbol(child, Decl(checkOrderDependenceGenericAssignability.ts, 20, 29))
+>a : Symbol(a, Decl(checkOrderDependenceGenericAssignability.ts, 20, 38))
+>b : Symbol(b, Decl(checkOrderDependenceGenericAssignability.ts, 20, 44))
+>child : Symbol(child, Decl(checkOrderDependenceGenericAssignability.ts, 20, 50))
+>parent : Symbol(parent, Decl(checkOrderDependenceGenericAssignability.ts, 20, 63))
+>parent : Symbol(parent, Decl(checkOrderDependenceGenericAssignability.ts, 20, 79))
+
+// Should error
+const notString: Parent<string> = pu;
+>notString : Symbol(notString, Decl(checkOrderDependenceGenericAssignability.ts, 23, 5))
+>Parent : Symbol(Parent, Decl(checkOrderDependenceGenericAssignability.ts, 0, 0))
+>pu : Symbol(pu, Decl(checkOrderDependenceGenericAssignability.ts, 20, 5))
+
diff --git a/tests/baselines/reference/checkOrderDependenceGenericAssignability.types b/tests/baselines/reference/checkOrderDependenceGenericAssignability.types
new file mode 100644
index 0000000000000..5bbdeb742ac41
--- /dev/null
+++ b/tests/baselines/reference/checkOrderDependenceGenericAssignability.types
@@ -0,0 +1,55 @@
+=== tests/cases/compiler/checkOrderDependenceGenericAssignability.ts ===
+// #44572
+
+interface Parent<A> {
+  child: Child<A> | null;
+>child : Child<A, unknown>
+>null : null
+
+  parent: Parent<A> | null;
+>parent : Parent<A>
+>null : null
+}
+
+interface Child<A, B = unknown> extends Parent<A> {
+  readonly a: A;
+>a : A
+
+  // This field isn't necessary to the repro, but the
+  // type parameter is, so including it
+  readonly b: B;
+>b : B
+}
+
+function fn<A>(inp: Child<A>) {
+>fn : <A>(inp: Child<A>) => void
+>inp : Child<A, unknown>
+
+  // This assignability check defeats the later one
+  const a: Child<unknown> = inp;
+>a : Child<unknown, unknown>
+>inp : Child<A, unknown>
+}
+
+// Allowed initialization of pu
+const pu: Parent<unknown> = { child: { a: 0, b: 0, child: null, parent: null }, parent: null };
+>pu : Parent<unknown>
+>{ child: { a: 0, b: 0, child: null, parent: null }, parent: null } : { child: { a: number; b: number; child: null; parent: null; }; parent: null; }
+>child : { a: number; b: number; child: null; parent: null; }
+>{ a: 0, b: 0, child: null, parent: null } : { a: number; b: number; child: null; parent: null; }
+>a : number
+>0 : 0
+>b : number
+>0 : 0
+>child : null
+>null : null
+>parent : null
+>null : null
+>parent : null
+>null : null
+
+// Should error
+const notString: Parent<string> = pu;
+>notString : Parent<string>
+>pu : Parent<unknown>
+
diff --git a/tests/baselines/reference/objectTypeWithRecursiveWrappedProperty.errors.txt b/tests/baselines/reference/objectTypeWithRecursiveWrappedProperty.errors.txt
index 582d7719a8976..e70e142573428 100644
--- a/tests/baselines/reference/objectTypeWithRecursiveWrappedProperty.errors.txt
+++ b/tests/baselines/reference/objectTypeWithRecursiveWrappedProperty.errors.txt
@@ -1,5 +1,6 @@
 tests/cases/conformance/types/typeRelationships/recursiveTypes/objectTypeWithRecursiveWrappedProperty.ts(13,1): error TS2322: Type 'List<string>' is not assignable to type 'List<number>'.
-  Type 'string' is not assignable to type 'number'.
+  Types of property 'data' are incompatible.
+    Type 'string' is not assignable to type 'number'.
 
 
 ==== tests/cases/conformance/types/typeRelationships/recursiveTypes/objectTypeWithRecursiveWrappedProperty.ts (1 errors) ====
@@ -18,4 +19,5 @@ tests/cases/conformance/types/typeRelationships/recursiveTypes/objectTypeWithRec
     list1 = list3; // error
     ~~~~~
 !!! error TS2322: Type 'List<string>' is not assignable to type 'List<number>'.
-!!! error TS2322:   Type 'string' is not assignable to type 'number'.
\ No newline at end of file
+!!! error TS2322:   Types of property 'data' are incompatible.
+!!! error TS2322:     Type 'string' is not assignable to type 'number'.
\ No newline at end of file
diff --git a/tests/baselines/reference/objectTypeWithRecursiveWrappedProperty2.errors.txt b/tests/baselines/reference/objectTypeWithRecursiveWrappedProperty2.errors.txt
index 6349a4528213a..a3905028d0dff 100644
--- a/tests/baselines/reference/objectTypeWithRecursiveWrappedProperty2.errors.txt
+++ b/tests/baselines/reference/objectTypeWithRecursiveWrappedProperty2.errors.txt
@@ -1,5 +1,6 @@
 tests/cases/conformance/types/typeRelationships/recursiveTypes/objectTypeWithRecursiveWrappedProperty2.ts(13,1): error TS2322: Type 'List<string>' is not assignable to type 'List<number>'.
-  Type 'string' is not assignable to type 'number'.
+  Types of property 'data' are incompatible.
+    Type 'string' is not assignable to type 'number'.
 
 
 ==== tests/cases/conformance/types/typeRelationships/recursiveTypes/objectTypeWithRecursiveWrappedProperty2.ts (1 errors) ====
@@ -18,4 +19,5 @@ tests/cases/conformance/types/typeRelationships/recursiveTypes/objectTypeWithRec
     list1 = list3; // error
     ~~~~~
 !!! error TS2322: Type 'List<string>' is not assignable to type 'List<number>'.
-!!! error TS2322:   Type 'string' is not assignable to type 'number'.
\ No newline at end of file
+!!! error TS2322:   Types of property 'data' are incompatible.
+!!! error TS2322:     Type 'string' is not assignable to type 'number'.
\ No newline at end of file
diff --git a/tests/baselines/reference/varianceMeasurement.errors.txt b/tests/baselines/reference/varianceMeasurement.errors.txt
index 4deb2d81e0b64..0869519529776 100644
--- a/tests/baselines/reference/varianceMeasurement.errors.txt
+++ b/tests/baselines/reference/varianceMeasurement.errors.txt
@@ -1,5 +1,11 @@
 tests/cases/compiler/varianceMeasurement.ts(10,7): error TS2322: Type 'Foo1<string>' is not assignable to type 'Foo1<"a">'.
-  Type 'string' is not assignable to type '"a"'.
+  Types of property 'x' are incompatible.
+    Type 'string' is not assignable to type '"a"'.
+tests/cases/compiler/varianceMeasurement.ts(11,7): error TS2322: Type 'Foo1<string>' is not assignable to type 'Foo1<unknown>'.
+  The types of 'y.x' are incompatible between these types.
+    Type '(arg: string) => void' is not assignable to type '(arg: unknown) => void'.
+      Types of parameters 'arg' and 'arg' are incompatible.
+        Type 'unknown' is not assignable to type 'string'.
 tests/cases/compiler/varianceMeasurement.ts(21,7): error TS2322: Type 'Foo2<string>' is not assignable to type 'Foo2<"a">'.
   Types of property 'x' are incompatible.
     Type 'string' is not assignable to type '"a"'.
@@ -19,14 +25,17 @@ tests/cases/compiler/varianceMeasurement.ts(45,7): error TS2322: Type 'Foo4<stri
       Types of parameters 'arg' and 'arg' are incompatible.
         Type 'unknown' is not assignable to type 'string'.
 tests/cases/compiler/varianceMeasurement.ts(57,7): error TS2322: Type 'Fn<string, number>' is not assignable to type 'Fn<unknown, number>'.
-  Type 'unknown' is not assignable to type 'string'.
+  The types returned by 'then(...)' are incompatible between these types.
+    Type 'Fn<string, any>' is not assignable to type 'Fn<unknown, any>'.
+      Types of parameters 'a' and 'a' are incompatible.
+        Type 'unknown' is not assignable to type 'string'.
 tests/cases/compiler/varianceMeasurement.ts(62,7): error TS2322: Type 'Fn<string, number>' is not assignable to type 'Fn<string, 0>'.
   Type 'number' is not assignable to type '0'.
 tests/cases/compiler/varianceMeasurement.ts(75,7): error TS2322: Type 'C<unknown, number>' is not assignable to type 'C<unknown, string>'.
   Type 'number' is not assignable to type 'string'.
 
 
-==== tests/cases/compiler/varianceMeasurement.ts (9 errors) ====
+==== tests/cases/compiler/varianceMeasurement.ts (10 errors) ====
     // The type below should be invariant in T but is measured as covariant because
     // we don't analyze recursive references.
     
@@ -39,8 +48,15 @@ tests/cases/compiler/varianceMeasurement.ts(75,7): error TS2322: Type 'C<unknown
     const f11: Foo1<'a'> = f10;
           ~~~
 !!! error TS2322: Type 'Foo1<string>' is not assignable to type 'Foo1<"a">'.
-!!! error TS2322:   Type 'string' is not assignable to type '"a"'.
+!!! error TS2322:   Types of property 'x' are incompatible.
+!!! error TS2322:     Type 'string' is not assignable to type '"a"'.
     const f12: Foo1<unknown> = f10;
+          ~~~
+!!! error TS2322: Type 'Foo1<string>' is not assignable to type 'Foo1<unknown>'.
+!!! error TS2322:   The types of 'y.x' are incompatible between these types.
+!!! error TS2322:     Type '(arg: string) => void' is not assignable to type '(arg: unknown) => void'.
+!!! error TS2322:       Types of parameters 'arg' and 'arg' are incompatible.
+!!! error TS2322:         Type 'unknown' is not assignable to type 'string'.
     
     // The type below is invariant in T and is measured as such.
     
@@ -112,7 +128,10 @@ tests/cases/compiler/varianceMeasurement.ts(75,7): error TS2322: Type 'C<unknown
     const fn1: Fn<unknown, number> = fn;  // Error
           ~~~
 !!! error TS2322: Type 'Fn<string, number>' is not assignable to type 'Fn<unknown, number>'.
-!!! error TS2322:   Type 'unknown' is not assignable to type 'string'.
+!!! error TS2322:   The types returned by 'then(...)' are incompatible between these types.
+!!! error TS2322:     Type 'Fn<string, any>' is not assignable to type 'Fn<unknown, any>'.
+!!! error TS2322:       Types of parameters 'a' and 'a' are incompatible.
+!!! error TS2322:         Type 'unknown' is not assignable to type 'string'.
     const fn2: Fn<'a', number> = fn;
     
     // Covariant in B
diff --git a/tests/cases/compiler/checkOrderDependenceGenericAssignability.ts b/tests/cases/compiler/checkOrderDependenceGenericAssignability.ts
new file mode 100644
index 0000000000000..508b1f3d8406d
--- /dev/null
+++ b/tests/cases/compiler/checkOrderDependenceGenericAssignability.ts
@@ -0,0 +1,24 @@
+// #44572
+
+interface Parent<A> {
+  child: Child<A> | null;
+  parent: Parent<A> | null;
+}
+
+interface Child<A, B = unknown> extends Parent<A> {
+  readonly a: A;
+  // This field isn't necessary to the repro, but the
+  // type parameter is, so including it
+  readonly b: B;
+}
+
+function fn<A>(inp: Child<A>) {
+  // This assignability check defeats the later one
+  const a: Child<unknown> = inp;
+}
+
+// Allowed initialization of pu
+const pu: Parent<unknown> = { child: { a: 0, b: 0, child: null, parent: null }, parent: null };
+
+// Should error
+const notString: Parent<string> = pu;