diff --git a/src/compiler/checker.ts b/src/compiler/checker.ts
index 781afe2cf9a84..530e734a552a2 100644
--- a/src/compiler/checker.ts
+++ b/src/compiler/checker.ts
@@ -36943,7 +36943,7 @@ namespace ts {
                 }
             }
 
-            checkMembersForMissingOverrideModifier(node, type, typeWithThis);
+            checkMembersForMissingOverrideModifier(node, type, typeWithThis, staticType);
 
             const implementedTypeNodes = getEffectiveImplementsTypeNodes(node);
             if (implementedTypeNodes) {
@@ -36980,13 +36980,18 @@ namespace ts {
             }
         }
 
-        function checkMembersForMissingOverrideModifier(node: ClassLikeDeclaration, type: InterfaceType, typeWithThis: Type) {
+        function checkMembersForMissingOverrideModifier(node: ClassLikeDeclaration, type: InterfaceType, typeWithThis: Type, staticType: ObjectType) {
             const nodeInAmbientContext = !!(node.flags & NodeFlags.Ambient);
             const baseTypeNode = getEffectiveBaseTypeNode(node);
             const baseTypes = baseTypeNode && getBaseTypes(type);
             const baseWithThis = baseTypes?.length ? getTypeWithThisArgument(first(baseTypes), type.thisType) : undefined;
+            const baseStaticType = getBaseConstructorTypeOfClass(type);
 
             for (const member of node.members) {
+                if (hasAmbientModifier(member)) {
+                    continue;
+                }
+
                 if (isConstructorDeclaration(member)) {
                     forEach(member.parameters, param => {
                         if (isParameterPropertyDeclaration(param, member)) {
@@ -36996,17 +37001,22 @@ namespace ts {
                 }
                 checkClassMember(member);
             }
+
             function checkClassMember(member: ClassElement | ParameterPropertyDeclaration, memberIsParameterProperty?: boolean) {
                 const hasOverride = hasOverrideModifier(member);
+                const hasStatic = hasStaticModifier(member);
                 if (baseWithThis && (hasOverride || compilerOptions.noImplicitOverride)) {
                     const declaredProp = member.name && getSymbolAtLocation(member.name) || getSymbolAtLocation(member);
                     if (!declaredProp) {
                         return;
                     }
 
+                    const thisType = hasStatic ? staticType : typeWithThis;
+                    const baseType = hasStatic ? baseStaticType : baseWithThis;
+                    const prop = getPropertyOfType(thisType, declaredProp.escapedName);
+                    const baseProp = getPropertyOfType(baseType, declaredProp.escapedName);
+
                     const baseClassName = typeToString(baseWithThis);
-                    const prop = getPropertyOfType(typeWithThis, declaredProp.escapedName);
-                    const baseProp = getPropertyOfType(baseWithThis, declaredProp.escapedName);
                     if (prop && !baseProp && hasOverride) {
                         error(member, Diagnostics.This_member_cannot_have_an_override_modifier_because_it_is_not_declared_in_the_base_class_0, baseClassName);
                     }
@@ -40443,9 +40453,6 @@ namespace ts {
                         else if (flags & ModifierFlags.Ambient) {
                             return grammarErrorOnNode(modifier, Diagnostics._0_modifier_cannot_be_used_with_1_modifier, "override", "declare");
                         }
-                        else if (flags & ModifierFlags.Static) {
-                            return grammarErrorOnNode(modifier, Diagnostics._0_modifier_cannot_be_used_with_1_modifier, "static", "override");
-                        }
                         else if (flags & ModifierFlags.Readonly) {
                             return grammarErrorOnNode(modifier, Diagnostics._0_modifier_must_precede_1_modifier, "override", "readonly");
                         }
@@ -40500,9 +40507,6 @@ namespace ts {
                         else if (flags & ModifierFlags.Readonly) {
                             return grammarErrorOnNode(modifier, Diagnostics._0_modifier_must_precede_1_modifier, "static", "readonly");
                         }
-                        else if (flags & ModifierFlags.Override) {
-                            return grammarErrorOnNode(modifier, Diagnostics._0_modifier_cannot_be_used_with_1_modifier, "static", "override");
-                        }
                         else if (flags & ModifierFlags.Async) {
                             return grammarErrorOnNode(modifier, Diagnostics._0_modifier_must_precede_1_modifier, "static", "async");
                         }
diff --git a/tests/baselines/reference/override13.errors.txt b/tests/baselines/reference/override13.errors.txt
new file mode 100644
index 0000000000000..3cc182018cdeb
--- /dev/null
+++ b/tests/baselines/reference/override13.errors.txt
@@ -0,0 +1,41 @@
+tests/cases/conformance/override/override13.ts(7,5): error TS4114: This member must have an 'override' modifier because it overrides a member in the base class 'Foo'.
+tests/cases/conformance/override/override13.ts(13,12): error TS4114: This member must have an 'override' modifier because it overrides a member in the base class 'Foo'.
+tests/cases/conformance/override/override13.ts(19,5): error TS4114: This member must have an 'override' modifier because it overrides a member in the base class 'Intermediate'.
+tests/cases/conformance/override/override13.ts(25,12): error TS4114: This member must have an 'override' modifier because it overrides a member in the base class 'Intermediate'.
+
+
+==== tests/cases/conformance/override/override13.ts (4 errors) ====
+    class Foo {
+        property = 1
+        static staticProperty = 2
+    }
+    
+    class SubFoo extends Foo {
+        property = 42;
+        ~~~~~~~~
+!!! error TS4114: This member must have an 'override' modifier because it overrides a member in the base class 'Foo'.
+        staticProperty = 42;
+    }
+    
+    class StaticSubFoo extends Foo {
+        static property = 42;
+        static staticProperty = 42;
+               ~~~~~~~~~~~~~~
+!!! error TS4114: This member must have an 'override' modifier because it overrides a member in the base class 'Foo'.
+    }
+    
+    class Intermediate extends Foo {}
+    
+    class Derived extends Intermediate {
+        property = 42;
+        ~~~~~~~~
+!!! error TS4114: This member must have an 'override' modifier because it overrides a member in the base class 'Intermediate'.
+        staticProperty = 42;
+    }
+    
+    class StaticDerived extends Intermediate {
+        static property = 42;
+        static staticProperty = 42;
+               ~~~~~~~~~~~~~~
+!!! error TS4114: This member must have an 'override' modifier because it overrides a member in the base class 'Intermediate'.
+    }
\ No newline at end of file
diff --git a/tests/baselines/reference/override13.js b/tests/baselines/reference/override13.js
new file mode 100644
index 0000000000000..96864a74142e1
--- /dev/null
+++ b/tests/baselines/reference/override13.js
@@ -0,0 +1,51 @@
+//// [override13.ts]
+class Foo {
+    property = 1
+    static staticProperty = 2
+}
+
+class SubFoo extends Foo {
+    property = 42;
+    staticProperty = 42;
+}
+
+class StaticSubFoo extends Foo {
+    static property = 42;
+    static staticProperty = 42;
+}
+
+class Intermediate extends Foo {}
+
+class Derived extends Intermediate {
+    property = 42;
+    staticProperty = 42;
+}
+
+class StaticDerived extends Intermediate {
+    static property = 42;
+    static staticProperty = 42;
+}
+
+//// [override13.js]
+class Foo {
+    property = 1;
+    static staticProperty = 2;
+}
+class SubFoo extends Foo {
+    property = 42;
+    staticProperty = 42;
+}
+class StaticSubFoo extends Foo {
+    static property = 42;
+    static staticProperty = 42;
+}
+class Intermediate extends Foo {
+}
+class Derived extends Intermediate {
+    property = 42;
+    staticProperty = 42;
+}
+class StaticDerived extends Intermediate {
+    static property = 42;
+    static staticProperty = 42;
+}
diff --git a/tests/baselines/reference/override13.symbols b/tests/baselines/reference/override13.symbols
new file mode 100644
index 0000000000000..70a377a2b8bee
--- /dev/null
+++ b/tests/baselines/reference/override13.symbols
@@ -0,0 +1,58 @@
+=== tests/cases/conformance/override/override13.ts ===
+class Foo {
+>Foo : Symbol(Foo, Decl(override13.ts, 0, 0))
+
+    property = 1
+>property : Symbol(Foo.property, Decl(override13.ts, 0, 11))
+
+    static staticProperty = 2
+>staticProperty : Symbol(Foo.staticProperty, Decl(override13.ts, 1, 16))
+}
+
+class SubFoo extends Foo {
+>SubFoo : Symbol(SubFoo, Decl(override13.ts, 3, 1))
+>Foo : Symbol(Foo, Decl(override13.ts, 0, 0))
+
+    property = 42;
+>property : Symbol(SubFoo.property, Decl(override13.ts, 5, 26))
+
+    staticProperty = 42;
+>staticProperty : Symbol(SubFoo.staticProperty, Decl(override13.ts, 6, 18))
+}
+
+class StaticSubFoo extends Foo {
+>StaticSubFoo : Symbol(StaticSubFoo, Decl(override13.ts, 8, 1))
+>Foo : Symbol(Foo, Decl(override13.ts, 0, 0))
+
+    static property = 42;
+>property : Symbol(StaticSubFoo.property, Decl(override13.ts, 10, 32))
+
+    static staticProperty = 42;
+>staticProperty : Symbol(StaticSubFoo.staticProperty, Decl(override13.ts, 11, 25))
+}
+
+class Intermediate extends Foo {}
+>Intermediate : Symbol(Intermediate, Decl(override13.ts, 13, 1))
+>Foo : Symbol(Foo, Decl(override13.ts, 0, 0))
+
+class Derived extends Intermediate {
+>Derived : Symbol(Derived, Decl(override13.ts, 15, 33))
+>Intermediate : Symbol(Intermediate, Decl(override13.ts, 13, 1))
+
+    property = 42;
+>property : Symbol(Derived.property, Decl(override13.ts, 17, 36))
+
+    staticProperty = 42;
+>staticProperty : Symbol(Derived.staticProperty, Decl(override13.ts, 18, 18))
+}
+
+class StaticDerived extends Intermediate {
+>StaticDerived : Symbol(StaticDerived, Decl(override13.ts, 20, 1))
+>Intermediate : Symbol(Intermediate, Decl(override13.ts, 13, 1))
+
+    static property = 42;
+>property : Symbol(StaticDerived.property, Decl(override13.ts, 22, 42))
+
+    static staticProperty = 42;
+>staticProperty : Symbol(StaticDerived.staticProperty, Decl(override13.ts, 23, 25))
+}
diff --git a/tests/baselines/reference/override13.types b/tests/baselines/reference/override13.types
new file mode 100644
index 0000000000000..44b59c3f4ae39
--- /dev/null
+++ b/tests/baselines/reference/override13.types
@@ -0,0 +1,68 @@
+=== tests/cases/conformance/override/override13.ts ===
+class Foo {
+>Foo : Foo
+
+    property = 1
+>property : number
+>1 : 1
+
+    static staticProperty = 2
+>staticProperty : number
+>2 : 2
+}
+
+class SubFoo extends Foo {
+>SubFoo : SubFoo
+>Foo : Foo
+
+    property = 42;
+>property : number
+>42 : 42
+
+    staticProperty = 42;
+>staticProperty : number
+>42 : 42
+}
+
+class StaticSubFoo extends Foo {
+>StaticSubFoo : StaticSubFoo
+>Foo : Foo
+
+    static property = 42;
+>property : number
+>42 : 42
+
+    static staticProperty = 42;
+>staticProperty : number
+>42 : 42
+}
+
+class Intermediate extends Foo {}
+>Intermediate : Intermediate
+>Foo : Foo
+
+class Derived extends Intermediate {
+>Derived : Derived
+>Intermediate : Intermediate
+
+    property = 42;
+>property : number
+>42 : 42
+
+    staticProperty = 42;
+>staticProperty : number
+>42 : 42
+}
+
+class StaticDerived extends Intermediate {
+>StaticDerived : StaticDerived
+>Intermediate : Intermediate
+
+    static property = 42;
+>property : number
+>42 : 42
+
+    static staticProperty = 42;
+>staticProperty : number
+>42 : 42
+}
diff --git a/tests/baselines/reference/override14.js b/tests/baselines/reference/override14.js
new file mode 100644
index 0000000000000..df69367bc5c7e
--- /dev/null
+++ b/tests/baselines/reference/override14.js
@@ -0,0 +1,16 @@
+//// [override14.ts]
+class Foo {
+    property = 1
+}
+
+class SubFoo extends Foo {
+    declare property: number
+}
+
+
+//// [override14.js]
+class Foo {
+    property = 1;
+}
+class SubFoo extends Foo {
+}
diff --git a/tests/baselines/reference/override14.symbols b/tests/baselines/reference/override14.symbols
new file mode 100644
index 0000000000000..483f1997c49f3
--- /dev/null
+++ b/tests/baselines/reference/override14.symbols
@@ -0,0 +1,16 @@
+=== tests/cases/conformance/override/override14.ts ===
+class Foo {
+>Foo : Symbol(Foo, Decl(override14.ts, 0, 0))
+
+    property = 1
+>property : Symbol(Foo.property, Decl(override14.ts, 0, 11))
+}
+
+class SubFoo extends Foo {
+>SubFoo : Symbol(SubFoo, Decl(override14.ts, 2, 1))
+>Foo : Symbol(Foo, Decl(override14.ts, 0, 0))
+
+    declare property: number
+>property : Symbol(SubFoo.property, Decl(override14.ts, 4, 26))
+}
+
diff --git a/tests/baselines/reference/override14.types b/tests/baselines/reference/override14.types
new file mode 100644
index 0000000000000..d566a28db2635
--- /dev/null
+++ b/tests/baselines/reference/override14.types
@@ -0,0 +1,17 @@
+=== tests/cases/conformance/override/override14.ts ===
+class Foo {
+>Foo : Foo
+
+    property = 1
+>property : number
+>1 : 1
+}
+
+class SubFoo extends Foo {
+>SubFoo : SubFoo
+>Foo : Foo
+
+    declare property: number
+>property : number
+}
+
diff --git a/tests/baselines/reference/override5.errors.txt b/tests/baselines/reference/override5.errors.txt
index 6c9c93aa1986c..e0dd689d47e39 100644
--- a/tests/baselines/reference/override5.errors.txt
+++ b/tests/baselines/reference/override5.errors.txt
@@ -1,7 +1,6 @@
-tests/cases/conformance/override/override5.ts(12,13): error TS4114: This member must have an 'override' modifier because it overrides a member in the base class 'B'.
 tests/cases/conformance/override/override5.ts(14,14): error TS1040: 'override' modifier cannot be used in an ambient context.
 tests/cases/conformance/override/override5.ts(16,14): error TS1029: 'override' modifier must precede 'readonly' modifier.
-tests/cases/conformance/override/override5.ts(20,14): error TS1243: 'static' modifier cannot be used with 'override' modifier.
+tests/cases/conformance/override/override5.ts(20,21): error TS4113: This member cannot have an 'override' modifier because it is not declared in the base class 'B'.
 tests/cases/conformance/override/override5.ts(22,14): error TS1030: 'override' modifier already seen.
 tests/cases/conformance/override/override5.ts(25,14): error TS1029: 'public' modifier must precede 'override' modifier.
 tests/cases/conformance/override/override5.ts(27,5): error TS1089: 'override' modifier cannot appear on a constructor declaration.
@@ -9,7 +8,7 @@ tests/cases/conformance/override/override5.ts(44,23): error TS4112: This member
 tests/cases/conformance/override/override5.ts(45,23): error TS4112: This member cannot have an 'override' modifier because its containing class 'AND' does not extend another class.
 
 
-==== tests/cases/conformance/override/override5.ts (9 errors) ====
+==== tests/cases/conformance/override/override5.ts (8 errors) ====
     class B {
         p1: number = 1;
         p2: number = 2;
@@ -22,8 +21,6 @@ tests/cases/conformance/override/override5.ts(45,23): error TS4112: This member
     
     class D extends B{
         declare p1: number
-                ~~
-!!! error TS4114: This member must have an 'override' modifier because it overrides a member in the base class 'B'.
     
         override declare p2: number;
                  ~~~~~~~
@@ -36,8 +33,8 @@ tests/cases/conformance/override/override5.ts(45,23): error TS4112: This member
         override readonly p4: number;
     
         override static sp: number;
-                 ~~~~~~
-!!! error TS1243: 'static' modifier cannot be used with 'override' modifier.
+                        ~~
+!!! error TS4113: This member cannot have an 'override' modifier because it is not declared in the base class 'B'.
     
         override override oop: number;
                  ~~~~~~~~
diff --git a/tests/baselines/reference/override7.errors.txt b/tests/baselines/reference/override7.errors.txt
index dec798252a28a..e5d908c99920c 100644
--- a/tests/baselines/reference/override7.errors.txt
+++ b/tests/baselines/reference/override7.errors.txt
@@ -1,6 +1,6 @@
 tests/cases/conformance/override/override7.ts(11,14): error TS1040: 'override' modifier cannot be used in an ambient context.
 tests/cases/conformance/override/override7.ts(13,14): error TS1029: 'override' modifier must precede 'readonly' modifier.
-tests/cases/conformance/override/override7.ts(17,14): error TS1243: 'static' modifier cannot be used with 'override' modifier.
+tests/cases/conformance/override/override7.ts(17,21): error TS4113: This member cannot have an 'override' modifier because it is not declared in the base class 'B'.
 tests/cases/conformance/override/override7.ts(19,14): error TS1030: 'override' modifier already seen.
 tests/cases/conformance/override/override7.ts(19,23): error TS4113: This member cannot have an 'override' modifier because it is not declared in the base class 'B'.
 tests/cases/conformance/override/override7.ts(21,21): error TS4113: This member cannot have an 'override' modifier because it is not declared in the base class 'B'.
@@ -33,8 +33,8 @@ tests/cases/conformance/override/override7.ts(42,23): error TS4112: This member
         override readonly p4: number;
     
         override static sp: number;
-                 ~~~~~~
-!!! error TS1243: 'static' modifier cannot be used with 'override' modifier.
+                        ~~
+!!! error TS4113: This member cannot have an 'override' modifier because it is not declared in the base class 'B'.
     
         override override oop: number;
                  ~~~~~~~~
diff --git a/tests/cases/conformance/override/override13.ts b/tests/cases/conformance/override/override13.ts
new file mode 100644
index 0000000000000..855df36af4a6e
--- /dev/null
+++ b/tests/cases/conformance/override/override13.ts
@@ -0,0 +1,29 @@
+// @noImplicitOverride: true
+// @target: esnext
+
+class Foo {
+    property = 1
+    static staticProperty = 2
+}
+
+class SubFoo extends Foo {
+    property = 42;
+    staticProperty = 42;
+}
+
+class StaticSubFoo extends Foo {
+    static property = 42;
+    static staticProperty = 42;
+}
+
+class Intermediate extends Foo {}
+
+class Derived extends Intermediate {
+    property = 42;
+    staticProperty = 42;
+}
+
+class StaticDerived extends Intermediate {
+    static property = 42;
+    static staticProperty = 42;
+}
\ No newline at end of file
diff --git a/tests/cases/conformance/override/override14.ts b/tests/cases/conformance/override/override14.ts
new file mode 100644
index 0000000000000..8fe638ba745d4
--- /dev/null
+++ b/tests/cases/conformance/override/override14.ts
@@ -0,0 +1,10 @@
+// @noImplicitOverride: true
+// @target: esnext
+
+class Foo {
+    property = 1
+}
+
+class SubFoo extends Foo {
+    declare property: number
+}