diff --git a/src/compiler/checker.ts b/src/compiler/checker.ts
index e763d5703fc..067b0e00030 100644
--- a/src/compiler/checker.ts
+++ b/src/compiler/checker.ts
@@ -24140,21 +24140,25 @@ namespace ts {
             }
         }
 
-        function isConstraintPosition(node: Node) {
+        function isConstraintPosition(type: Type, node: Node) {
             const parent = node.parent;
-            // In an element access obj[x], we consider obj to be in a constraint position only when x is not
-            // of a generic type. This is because when both obj and x are of generic types T and K, we want
-            // the resulting type to be T[K].
+            // In an element access obj[x], we consider obj to be in a constraint position, except when obj is of
+            // a generic type without a nullable constraint and x is a generic type. This is because when both obj
+            // and x are of generic types T and K, we want the resulting type to be T[K].
             return parent.kind === SyntaxKind.PropertyAccessExpression ||
                 parent.kind === SyntaxKind.CallExpression && (parent as CallExpression).expression === node ||
                 parent.kind === SyntaxKind.ElementAccessExpression && (parent as ElementAccessExpression).expression === node &&
-                    !isGenericIndexType(getTypeOfExpression((parent as ElementAccessExpression).argumentExpression));
+                    !(isGenericTypeWithoutNullableConstraint(type) && isGenericIndexType(getTypeOfExpression((parent as ElementAccessExpression).argumentExpression)));
         }
 
         function isGenericTypeWithUnionConstraint(type: Type) {
             return !!(type.flags & TypeFlags.Instantiable && getBaseConstraintOrType(type).flags & (TypeFlags.Nullable | TypeFlags.Union));
         }
 
+        function isGenericTypeWithoutNullableConstraint(type: Type) {
+            return !!(type.flags & TypeFlags.Instantiable && !maybeTypeOfKind(getBaseConstraintOrType(type), TypeFlags.Nullable));
+        }
+
         function containsGenericType(type: Type): boolean {
             return !!(type.flags & TypeFlags.Instantiable || type.flags & TypeFlags.UnionOrIntersection && some((type as UnionOrIntersectionType).types, containsGenericType));
         }
@@ -24178,7 +24182,7 @@ namespace ts {
             // 'string | undefined' to give control flow analysis the opportunity to narrow to type 'string'.
             const substituteConstraints = !(checkMode && checkMode & CheckMode.Inferential) &&
                 someType(type, isGenericTypeWithUnionConstraint) &&
-                (isConstraintPosition(reference) || hasNonBindingPatternContextualTypeWithNoGenericTypes(reference));
+                (isConstraintPosition(type, reference) || hasNonBindingPatternContextualTypeWithNoGenericTypes(reference));
             return substituteConstraints ? mapType(type, t => t.flags & TypeFlags.Instantiable ? getBaseConstraintOrType(t) : t) : type;
         }
 
diff --git a/tests/baselines/reference/controlFlowGenericTypes.errors.txt b/tests/baselines/reference/controlFlowGenericTypes.errors.txt
index 36d9e896317..d6bd2aba7be 100644
--- a/tests/baselines/reference/controlFlowGenericTypes.errors.txt
+++ b/tests/baselines/reference/controlFlowGenericTypes.errors.txt
@@ -5,9 +5,12 @@ tests/cases/conformance/controlFlow/controlFlowGenericTypes.ts(81,11): error TS2
 tests/cases/conformance/controlFlow/controlFlowGenericTypes.ts(90,44): error TS2355: A function whose declared type is neither 'void' nor 'any' must return a value.
 tests/cases/conformance/controlFlow/controlFlowGenericTypes.ts(91,11): error TS2339: Property 'foo' does not exist on type 'MyUnion'.
   Property 'foo' does not exist on type 'AA'.
+tests/cases/conformance/controlFlow/controlFlowGenericTypes.ts(156,16): error TS2532: Object is possibly 'undefined'.
+tests/cases/conformance/controlFlow/controlFlowGenericTypes.ts(167,9): error TS2532: Object is possibly 'undefined'.
+tests/cases/conformance/controlFlow/controlFlowGenericTypes.ts(168,9): error TS2532: Object is possibly 'undefined'.
 
 
-==== tests/cases/conformance/controlFlow/controlFlowGenericTypes.ts (5 errors) ====
+==== tests/cases/conformance/controlFlow/controlFlowGenericTypes.ts (8 errors) ====
     function f1<T extends string | undefined>(x: T, y: { a: T }, z: [T]): string {
         if (x) {
             x;
@@ -159,4 +162,46 @@ tests/cases/conformance/controlFlow/controlFlowGenericTypes.ts(91,11): error TS2
         emittingObject.off(eventName, 0);
         emittingObject.off(eventName as typeof eventName, 0);
     }
+    
+    // In an element access obj[x], we consider obj to be in a constraint position, except when obj is of
+    // a generic type without a nullable constraint and x is a generic type. This is because when both obj
+    // and x are of generic types T and K, we want the resulting type to be T[K].
+    
+    function fx1<T, K extends keyof T>(obj: T, key: K) {
+        const x1 = obj[key];
+        const x2 = obj && obj[key];
+    }
+    
+    function fx2<T extends Record<keyof T, string>, K extends keyof T>(obj: T, key: K) {
+        const x1 = obj[key];
+        const x2 = obj && obj[key];
+    }
+    
+    function fx3<T extends Record<keyof T, string> | undefined, K extends keyof T>(obj: T, key: K) {
+        const x1 = obj[key];  // Error
+                   ~~~
+!!! error TS2532: Object is possibly 'undefined'.
+        const x2 = obj && obj[key];
+    }
+    
+    // Repro from #44166
+    
+    class TableBaseEnum<
+        PublicSpec extends Record<keyof InternalSpec, any>,
+        InternalSpec extends Record<keyof PublicSpec, any>  | undefined = undefined> {
+        m() {
+            let iSpec = null! as InternalSpec;
+            iSpec[null! as keyof InternalSpec];  // Error, object possibly undefined
+            ~~~~~
+!!! error TS2532: Object is possibly 'undefined'.
+            iSpec[null! as keyof PublicSpec];    // Error, object possibly undefined
+            ~~~~~
+!!! error TS2532: Object is possibly 'undefined'.
+            if (iSpec === undefined) {
+                return;
+            }
+            iSpec[null! as keyof InternalSpec];
+            iSpec[null! as keyof PublicSpec];
+        }
+    }
     
\ No newline at end of file
diff --git a/tests/baselines/reference/controlFlowGenericTypes.js b/tests/baselines/reference/controlFlowGenericTypes.js
index 17b8e0dd4e0..d6acd179b69 100644
--- a/tests/baselines/reference/controlFlowGenericTypes.js
+++ b/tests/baselines/reference/controlFlowGenericTypes.js
@@ -138,6 +138,42 @@ function once<ET, T extends EventEmitter<ET>>(emittingObject: T, eventName: keyo
     emittingObject.off(eventName, 0);
     emittingObject.off(eventName as typeof eventName, 0);
 }
+
+// In an element access obj[x], we consider obj to be in a constraint position, except when obj is of
+// a generic type without a nullable constraint and x is a generic type. This is because when both obj
+// and x are of generic types T and K, we want the resulting type to be T[K].
+
+function fx1<T, K extends keyof T>(obj: T, key: K) {
+    const x1 = obj[key];
+    const x2 = obj && obj[key];
+}
+
+function fx2<T extends Record<keyof T, string>, K extends keyof T>(obj: T, key: K) {
+    const x1 = obj[key];
+    const x2 = obj && obj[key];
+}
+
+function fx3<T extends Record<keyof T, string> | undefined, K extends keyof T>(obj: T, key: K) {
+    const x1 = obj[key];  // Error
+    const x2 = obj && obj[key];
+}
+
+// Repro from #44166
+
+class TableBaseEnum<
+    PublicSpec extends Record<keyof InternalSpec, any>,
+    InternalSpec extends Record<keyof PublicSpec, any>  | undefined = undefined> {
+    m() {
+        let iSpec = null! as InternalSpec;
+        iSpec[null! as keyof InternalSpec];  // Error, object possibly undefined
+        iSpec[null! as keyof PublicSpec];    // Error, object possibly undefined
+        if (iSpec === undefined) {
+            return;
+        }
+        iSpec[null! as keyof InternalSpec];
+        iSpec[null! as keyof PublicSpec];
+    }
+}
 
 
 //// [controlFlowGenericTypes.js]
@@ -246,3 +282,34 @@ function once(emittingObject, eventName) {
     emittingObject.off(eventName, 0);
     emittingObject.off(eventName, 0);
 }
+// In an element access obj[x], we consider obj to be in a constraint position, except when obj is of
+// a generic type without a nullable constraint and x is a generic type. This is because when both obj
+// and x are of generic types T and K, we want the resulting type to be T[K].
+function fx1(obj, key) {
+    var x1 = obj[key];
+    var x2 = obj && obj[key];
+}
+function fx2(obj, key) {
+    var x1 = obj[key];
+    var x2 = obj && obj[key];
+}
+function fx3(obj, key) {
+    var x1 = obj[key]; // Error
+    var x2 = obj && obj[key];
+}
+// Repro from #44166
+var TableBaseEnum = /** @class */ (function () {
+    function TableBaseEnum() {
+    }
+    TableBaseEnum.prototype.m = function () {
+        var iSpec = null;
+        iSpec[null]; // Error, object possibly undefined
+        iSpec[null]; // Error, object possibly undefined
+        if (iSpec === undefined) {
+            return;
+        }
+        iSpec[null];
+        iSpec[null];
+    };
+    return TableBaseEnum;
+}());
diff --git a/tests/baselines/reference/controlFlowGenericTypes.symbols b/tests/baselines/reference/controlFlowGenericTypes.symbols
index 61597dfdf9d..0ea62c53221 100644
--- a/tests/baselines/reference/controlFlowGenericTypes.symbols
+++ b/tests/baselines/reference/controlFlowGenericTypes.symbols
@@ -405,3 +405,123 @@ function once<ET, T extends EventEmitter<ET>>(emittingObject: T, eventName: keyo
 >eventName : Symbol(eventName, Decl(controlFlowGenericTypes.ts, 135, 64))
 }
 
+// In an element access obj[x], we consider obj to be in a constraint position, except when obj is of
+// a generic type without a nullable constraint and x is a generic type. This is because when both obj
+// and x are of generic types T and K, we want the resulting type to be T[K].
+
+function fx1<T, K extends keyof T>(obj: T, key: K) {
+>fx1 : Symbol(fx1, Decl(controlFlowGenericTypes.ts, 138, 1))
+>T : Symbol(T, Decl(controlFlowGenericTypes.ts, 144, 13))
+>K : Symbol(K, Decl(controlFlowGenericTypes.ts, 144, 15))
+>T : Symbol(T, Decl(controlFlowGenericTypes.ts, 144, 13))
+>obj : Symbol(obj, Decl(controlFlowGenericTypes.ts, 144, 35))
+>T : Symbol(T, Decl(controlFlowGenericTypes.ts, 144, 13))
+>key : Symbol(key, Decl(controlFlowGenericTypes.ts, 144, 42))
+>K : Symbol(K, Decl(controlFlowGenericTypes.ts, 144, 15))
+
+    const x1 = obj[key];
+>x1 : Symbol(x1, Decl(controlFlowGenericTypes.ts, 145, 9))
+>obj : Symbol(obj, Decl(controlFlowGenericTypes.ts, 144, 35))
+>key : Symbol(key, Decl(controlFlowGenericTypes.ts, 144, 42))
+
+    const x2 = obj && obj[key];
+>x2 : Symbol(x2, Decl(controlFlowGenericTypes.ts, 146, 9))
+>obj : Symbol(obj, Decl(controlFlowGenericTypes.ts, 144, 35))
+>obj : Symbol(obj, Decl(controlFlowGenericTypes.ts, 144, 35))
+>key : Symbol(key, Decl(controlFlowGenericTypes.ts, 144, 42))
+}
+
+function fx2<T extends Record<keyof T, string>, K extends keyof T>(obj: T, key: K) {
+>fx2 : Symbol(fx2, Decl(controlFlowGenericTypes.ts, 147, 1))
+>T : Symbol(T, Decl(controlFlowGenericTypes.ts, 149, 13))
+>Record : Symbol(Record, Decl(lib.es5.d.ts, --, --))
+>T : Symbol(T, Decl(controlFlowGenericTypes.ts, 149, 13))
+>K : Symbol(K, Decl(controlFlowGenericTypes.ts, 149, 47))
+>T : Symbol(T, Decl(controlFlowGenericTypes.ts, 149, 13))
+>obj : Symbol(obj, Decl(controlFlowGenericTypes.ts, 149, 67))
+>T : Symbol(T, Decl(controlFlowGenericTypes.ts, 149, 13))
+>key : Symbol(key, Decl(controlFlowGenericTypes.ts, 149, 74))
+>K : Symbol(K, Decl(controlFlowGenericTypes.ts, 149, 47))
+
+    const x1 = obj[key];
+>x1 : Symbol(x1, Decl(controlFlowGenericTypes.ts, 150, 9))
+>obj : Symbol(obj, Decl(controlFlowGenericTypes.ts, 149, 67))
+>key : Symbol(key, Decl(controlFlowGenericTypes.ts, 149, 74))
+
+    const x2 = obj && obj[key];
+>x2 : Symbol(x2, Decl(controlFlowGenericTypes.ts, 151, 9))
+>obj : Symbol(obj, Decl(controlFlowGenericTypes.ts, 149, 67))
+>obj : Symbol(obj, Decl(controlFlowGenericTypes.ts, 149, 67))
+>key : Symbol(key, Decl(controlFlowGenericTypes.ts, 149, 74))
+}
+
+function fx3<T extends Record<keyof T, string> | undefined, K extends keyof T>(obj: T, key: K) {
+>fx3 : Symbol(fx3, Decl(controlFlowGenericTypes.ts, 152, 1))
+>T : Symbol(T, Decl(controlFlowGenericTypes.ts, 154, 13))
+>Record : Symbol(Record, Decl(lib.es5.d.ts, --, --))
+>T : Symbol(T, Decl(controlFlowGenericTypes.ts, 154, 13))
+>K : Symbol(K, Decl(controlFlowGenericTypes.ts, 154, 59))
+>T : Symbol(T, Decl(controlFlowGenericTypes.ts, 154, 13))
+>obj : Symbol(obj, Decl(controlFlowGenericTypes.ts, 154, 79))
+>T : Symbol(T, Decl(controlFlowGenericTypes.ts, 154, 13))
+>key : Symbol(key, Decl(controlFlowGenericTypes.ts, 154, 86))
+>K : Symbol(K, Decl(controlFlowGenericTypes.ts, 154, 59))
+
+    const x1 = obj[key];  // Error
+>x1 : Symbol(x1, Decl(controlFlowGenericTypes.ts, 155, 9))
+>obj : Symbol(obj, Decl(controlFlowGenericTypes.ts, 154, 79))
+>key : Symbol(key, Decl(controlFlowGenericTypes.ts, 154, 86))
+
+    const x2 = obj && obj[key];
+>x2 : Symbol(x2, Decl(controlFlowGenericTypes.ts, 156, 9))
+>obj : Symbol(obj, Decl(controlFlowGenericTypes.ts, 154, 79))
+>obj : Symbol(obj, Decl(controlFlowGenericTypes.ts, 154, 79))
+>key : Symbol(key, Decl(controlFlowGenericTypes.ts, 154, 86))
+}
+
+// Repro from #44166
+
+class TableBaseEnum<
+>TableBaseEnum : Symbol(TableBaseEnum, Decl(controlFlowGenericTypes.ts, 157, 1))
+
+    PublicSpec extends Record<keyof InternalSpec, any>,
+>PublicSpec : Symbol(PublicSpec, Decl(controlFlowGenericTypes.ts, 161, 20))
+>Record : Symbol(Record, Decl(lib.es5.d.ts, --, --))
+>InternalSpec : Symbol(InternalSpec, Decl(controlFlowGenericTypes.ts, 162, 55))
+
+    InternalSpec extends Record<keyof PublicSpec, any>  | undefined = undefined> {
+>InternalSpec : Symbol(InternalSpec, Decl(controlFlowGenericTypes.ts, 162, 55))
+>Record : Symbol(Record, Decl(lib.es5.d.ts, --, --))
+>PublicSpec : Symbol(PublicSpec, Decl(controlFlowGenericTypes.ts, 161, 20))
+
+    m() {
+>m : Symbol(TableBaseEnum.m, Decl(controlFlowGenericTypes.ts, 163, 82))
+
+        let iSpec = null! as InternalSpec;
+>iSpec : Symbol(iSpec, Decl(controlFlowGenericTypes.ts, 165, 11))
+>InternalSpec : Symbol(InternalSpec, Decl(controlFlowGenericTypes.ts, 162, 55))
+
+        iSpec[null! as keyof InternalSpec];  // Error, object possibly undefined
+>iSpec : Symbol(iSpec, Decl(controlFlowGenericTypes.ts, 165, 11))
+>InternalSpec : Symbol(InternalSpec, Decl(controlFlowGenericTypes.ts, 162, 55))
+
+        iSpec[null! as keyof PublicSpec];    // Error, object possibly undefined
+>iSpec : Symbol(iSpec, Decl(controlFlowGenericTypes.ts, 165, 11))
+>PublicSpec : Symbol(PublicSpec, Decl(controlFlowGenericTypes.ts, 161, 20))
+
+        if (iSpec === undefined) {
+>iSpec : Symbol(iSpec, Decl(controlFlowGenericTypes.ts, 165, 11))
+>undefined : Symbol(undefined)
+
+            return;
+        }
+        iSpec[null! as keyof InternalSpec];
+>iSpec : Symbol(iSpec, Decl(controlFlowGenericTypes.ts, 165, 11))
+>InternalSpec : Symbol(InternalSpec, Decl(controlFlowGenericTypes.ts, 162, 55))
+
+        iSpec[null! as keyof PublicSpec];
+>iSpec : Symbol(iSpec, Decl(controlFlowGenericTypes.ts, 165, 11))
+>PublicSpec : Symbol(PublicSpec, Decl(controlFlowGenericTypes.ts, 161, 20))
+    }
+}
+
diff --git a/tests/baselines/reference/controlFlowGenericTypes.types b/tests/baselines/reference/controlFlowGenericTypes.types
index 8c62c6dfa12..69b5854360d 100644
--- a/tests/baselines/reference/controlFlowGenericTypes.types
+++ b/tests/baselines/reference/controlFlowGenericTypes.types
@@ -388,3 +388,120 @@ function once<ET, T extends EventEmitter<ET>>(emittingObject: T, eventName: keyo
 >0 : 0
 }
 
+// In an element access obj[x], we consider obj to be in a constraint position, except when obj is of
+// a generic type without a nullable constraint and x is a generic type. This is because when both obj
+// and x are of generic types T and K, we want the resulting type to be T[K].
+
+function fx1<T, K extends keyof T>(obj: T, key: K) {
+>fx1 : <T, K extends keyof T>(obj: T, key: K) => void
+>obj : T
+>key : K
+
+    const x1 = obj[key];
+>x1 : T[K]
+>obj[key] : T[K]
+>obj : T
+>key : K
+
+    const x2 = obj && obj[key];
+>x2 : T[K]
+>obj && obj[key] : T[K]
+>obj : T
+>obj[key] : T[K]
+>obj : T
+>key : K
+}
+
+function fx2<T extends Record<keyof T, string>, K extends keyof T>(obj: T, key: K) {
+>fx2 : <T extends Record<keyof T, string>, K extends keyof T>(obj: T, key: K) => void
+>obj : T
+>key : K
+
+    const x1 = obj[key];
+>x1 : T[K]
+>obj[key] : T[K]
+>obj : T
+>key : K
+
+    const x2 = obj && obj[key];
+>x2 : T[K]
+>obj && obj[key] : T[K]
+>obj : T
+>obj[key] : T[K]
+>obj : T
+>key : K
+}
+
+function fx3<T extends Record<keyof T, string> | undefined, K extends keyof T>(obj: T, key: K) {
+>fx3 : <T extends Record<keyof T, string> | undefined, K extends keyof T>(obj: T, key: K) => void
+>obj : T
+>key : K
+
+    const x1 = obj[key];  // Error
+>x1 : NonNullable<Record<keyof T, string>>[K]
+>obj[key] : NonNullable<Record<keyof T, string>>[K]
+>obj : Record<keyof T, string> | undefined
+>key : K
+
+    const x2 = obj && obj[key];
+>x2 : Record<keyof T, string>[K]
+>obj && obj[key] : Record<keyof T, string>[K]
+>obj : T
+>obj[key] : Record<keyof T, string>[K]
+>obj : Record<keyof T, string>
+>key : K
+}
+
+// Repro from #44166
+
+class TableBaseEnum<
+>TableBaseEnum : TableBaseEnum<PublicSpec, InternalSpec>
+
+    PublicSpec extends Record<keyof InternalSpec, any>,
+    InternalSpec extends Record<keyof PublicSpec, any>  | undefined = undefined> {
+    m() {
+>m : () => void
+
+        let iSpec = null! as InternalSpec;
+>iSpec : InternalSpec
+>null! as InternalSpec : InternalSpec
+>null! : never
+>null : null
+
+        iSpec[null! as keyof InternalSpec];  // Error, object possibly undefined
+>iSpec[null! as keyof InternalSpec] : NonNullable<Record<keyof PublicSpec, any>>[keyof InternalSpec]
+>iSpec : Record<keyof PublicSpec, any> | undefined
+>null! as keyof InternalSpec : keyof InternalSpec
+>null! : never
+>null : null
+
+        iSpec[null! as keyof PublicSpec];    // Error, object possibly undefined
+>iSpec[null! as keyof PublicSpec] : NonNullable<Record<keyof PublicSpec, any>>[keyof PublicSpec]
+>iSpec : Record<keyof PublicSpec, any> | undefined
+>null! as keyof PublicSpec : keyof PublicSpec
+>null! : never
+>null : null
+
+        if (iSpec === undefined) {
+>iSpec === undefined : boolean
+>iSpec : InternalSpec
+>undefined : undefined
+
+            return;
+        }
+        iSpec[null! as keyof InternalSpec];
+>iSpec[null! as keyof InternalSpec] : Record<keyof PublicSpec, any>[keyof InternalSpec]
+>iSpec : Record<keyof PublicSpec, any>
+>null! as keyof InternalSpec : keyof InternalSpec
+>null! : never
+>null : null
+
+        iSpec[null! as keyof PublicSpec];
+>iSpec[null! as keyof PublicSpec] : Record<keyof PublicSpec, any>[keyof PublicSpec]
+>iSpec : Record<keyof PublicSpec, any>
+>null! as keyof PublicSpec : keyof PublicSpec
+>null! : never
+>null : null
+    }
+}
+
diff --git a/tests/cases/conformance/controlFlow/controlFlowGenericTypes.ts b/tests/cases/conformance/controlFlow/controlFlowGenericTypes.ts
index 21dbde8c33c..7c38ee8c671 100644
--- a/tests/cases/conformance/controlFlow/controlFlowGenericTypes.ts
+++ b/tests/cases/conformance/controlFlow/controlFlowGenericTypes.ts
@@ -139,3 +139,39 @@ function once<ET, T extends EventEmitter<ET>>(emittingObject: T, eventName: keyo
     emittingObject.off(eventName, 0);
     emittingObject.off(eventName as typeof eventName, 0);
 }
+
+// In an element access obj[x], we consider obj to be in a constraint position, except when obj is of
+// a generic type without a nullable constraint and x is a generic type. This is because when both obj
+// and x are of generic types T and K, we want the resulting type to be T[K].
+
+function fx1<T, K extends keyof T>(obj: T, key: K) {
+    const x1 = obj[key];
+    const x2 = obj && obj[key];
+}
+
+function fx2<T extends Record<keyof T, string>, K extends keyof T>(obj: T, key: K) {
+    const x1 = obj[key];
+    const x2 = obj && obj[key];
+}
+
+function fx3<T extends Record<keyof T, string> | undefined, K extends keyof T>(obj: T, key: K) {
+    const x1 = obj[key];  // Error
+    const x2 = obj && obj[key];
+}
+
+// Repro from #44166
+
+class TableBaseEnum<
+    PublicSpec extends Record<keyof InternalSpec, any>,
+    InternalSpec extends Record<keyof PublicSpec, any>  | undefined = undefined> {
+    m() {
+        let iSpec = null! as InternalSpec;
+        iSpec[null! as keyof InternalSpec];  // Error, object possibly undefined
+        iSpec[null! as keyof PublicSpec];    // Error, object possibly undefined
+        if (iSpec === undefined) {
+            return;
+        }
+        iSpec[null! as keyof InternalSpec];
+        iSpec[null! as keyof PublicSpec];
+    }
+}