diff --git a/internal/checker/checker.go b/internal/checker/checker.go
index 6a2fac5cf7..54477d5a77 100644
--- a/internal/checker/checker.go
+++ b/internal/checker/checker.go
@@ -24325,6 +24325,9 @@ func (c *Checker) getConditionalFlowTypeOfType(t *Type, node *ast.Node) *Type {
 	covariant := true
 	for node != nil && !ast.IsStatement(node) && node.Kind != ast.KindJSDoc {
 		parent := node.Parent
+		if parent == nil {
+			break
+		}
 		// only consider variance flipped by parameter locations - `keyof` types would usually be considered variance inverting, but
 		// often get used in indexed accesses where they behave sortof invariantly, but our checking is lax
 		if ast.IsParameter(parent) {
diff --git a/internal/diagnostics/diagnostics_generated.go b/internal/diagnostics/diagnostics_generated.go
index 2f9700f818..da5800eb6b 100644
--- a/internal/diagnostics/diagnostics_generated.go
+++ b/internal/diagnostics/diagnostics_generated.go
@@ -3522,6 +3522,8 @@ var Decorators_may_not_appear_after_export_or_export_default_if_they_also_appear
 
 var A_JSDoc_template_tag_may_not_follow_a_typedef_callback_or_overload_tag = &Message{code: 8039, category: CategoryError, key: "A_JSDoc_template_tag_may_not_follow_a_typedef_callback_or_overload_tag_8039", text: "A JSDoc '@template' tag may not follow a '@typedef', '@callback', or '@overload' tag"}
 
+var A_JSDoc_overload_tag_is_not_allowed_in_this_context = &Message{code: 8110, category: CategoryError, key: "A_JSDoc_overload_tag_is_not_allowed_in_this_context_8110", text: "A JSDoc '@overload' tag is not allowed in this context."}
+
 var Declaration_emit_for_this_file_requires_using_private_name_0_An_explicit_type_annotation_may_unblock_declaration_emit = &Message{code: 9005, category: CategoryError, key: "Declaration_emit_for_this_file_requires_using_private_name_0_An_explicit_type_annotation_may_unblock_9005", text: "Declaration emit for this file requires using private name '{0}'. An explicit type annotation may unblock declaration emit."}
 
 var Declaration_emit_for_this_file_requires_using_private_name_0_from_module_1_An_explicit_type_annotation_may_unblock_declaration_emit = &Message{code: 9006, category: CategoryError, key: "Declaration_emit_for_this_file_requires_using_private_name_0_from_module_1_An_explicit_type_annotati_9006", text: "Declaration emit for this file requires using private name '{0}' from module '{1}'. An explicit type annotation may unblock declaration emit."}
@@ -7792,6 +7794,8 @@ func keyToMessage(key Key) *Message {
 		return Decorators_may_not_appear_after_export_or_export_default_if_they_also_appear_before_export
 	case "A_JSDoc_template_tag_may_not_follow_a_typedef_callback_or_overload_tag_8039":
 		return A_JSDoc_template_tag_may_not_follow_a_typedef_callback_or_overload_tag
+	case "A_JSDoc_overload_tag_is_not_allowed_in_this_context_8110":
+		return A_JSDoc_overload_tag_is_not_allowed_in_this_context
 	case "Declaration_emit_for_this_file_requires_using_private_name_0_An_explicit_type_annotation_may_unblock_9005":
 		return Declaration_emit_for_this_file_requires_using_private_name_0_An_explicit_type_annotation_may_unblock_declaration_emit
 	case "Declaration_emit_for_this_file_requires_using_private_name_0_from_module_1_An_explicit_type_annotati_9006":
diff --git a/internal/diagnostics/extraDiagnosticMessages.json b/internal/diagnostics/extraDiagnosticMessages.json
index 2c916ca5f8..b1f0fca91c 100644
--- a/internal/diagnostics/extraDiagnosticMessages.json
+++ b/internal/diagnostics/extraDiagnosticMessages.json
@@ -74,5 +74,9 @@
     "Option '--incremental' is only valid with a known configuration file (like 'tsconfig.json') or when '--tsBuildInfoFile' is explicitly provided.": {
         "category": "Error",
         "code": 5074
+    },
+    "A JSDoc '@overload' tag is not allowed in this context.": {
+        "category": "Error",
+        "code": 8110
     }
 }
diff --git a/internal/parser/reparser.go b/internal/parser/reparser.go
index c795ad3d82..57aa3eb5ee 100644
--- a/internal/parser/reparser.go
+++ b/internal/parser/reparser.go
@@ -3,6 +3,7 @@ package parser
 import (
 	"github.com/microsoft/typescript-go/internal/ast"
 	"github.com/microsoft/typescript-go/internal/core"
+	"github.com/microsoft/typescript-go/internal/diagnostics"
 )
 
 func (p *Parser) finishReparsedNode(node *ast.Node, locationNode *ast.Node) {
@@ -112,7 +113,20 @@ func (p *Parser) reparseUnhosted(tag *ast.Node, parent *ast.Node, jsDoc *ast.Nod
 		p.reparseList = append(p.reparseList, importDeclaration)
 	case ast.KindJSDocOverloadTag:
 		if fun, ok := getFunctionLikeHost(parent); ok {
-			p.reparseList = append(p.reparseList, p.reparseJSDocSignature(tag.AsJSDocOverloadTag().TypeExpression, fun, jsDoc, tag, fun.Modifiers()))
+			// Only allow @overload on function declarations and class/interface method declarations.
+			// Disallow on object literal methods by checking if we're in the ObjectLiteralMembers parsing context.
+			isObjectLiteralMethod := parent.Kind == ast.KindMethodDeclaration &&
+				p.parsingContexts&(1<<PCObjectLiteralMembers) != 0
+
+			if !isObjectLiteralMethod &&
+				(parent.Kind == ast.KindFunctionDeclaration ||
+					parent.Kind == ast.KindMethodDeclaration ||
+					parent.Kind == ast.KindMethodSignature) {
+				p.reparseList = append(p.reparseList, p.reparseJSDocSignature(tag.AsJSDocOverloadTag().TypeExpression, fun, jsDoc, tag, fun.Modifiers()))
+			} else {
+				// Report error for @overload on object literal methods
+				p.parseErrorAtRange(tag.TagName().Loc, diagnostics.A_JSDoc_overload_tag_is_not_allowed_in_this_context)
+			}
 		}
 	}
 }
diff --git a/testdata/baselines/reference/compiler/nilPointerInConditionalFlowType.errors.txt b/testdata/baselines/reference/compiler/nilPointerInConditionalFlowType.errors.txt
new file mode 100644
index 0000000000..66298bbec9
--- /dev/null
+++ b/testdata/baselines/reference/compiler/nilPointerInConditionalFlowType.errors.txt
@@ -0,0 +1,30 @@
+test.js(20,15): error TS2355: A function whose declared type is neither 'undefined', 'void', nor 'any' must return a value.
+
+
+==== test.js (1 errors) ====
+    const foo = {
+    	/**
+    	 * @overload
+    	 * @param {string} termCode
+    	 * @param {string[]} crnList
+    	 * @param {string} sis
+    	 * @returns {Record<string, string>}
+    	 */
+    	/**
+    	 * @overload
+    	 * @param {string} termCode
+    	 * @param {string} crn
+    	 * @param {string} sis
+    	 * @returns {string}
+    	 */
+    	/**
+    	 * @param {string} termCode
+    	 * @param {string | string[]} crnList
+    	 * @param {string} sis
+    	 * @returns {string | Record<string, string>}
+    	             ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~
+!!! error TS2355: A function whose declared type is neither 'undefined', 'void', nor 'any' must return a value.
+    	 */
+    	getStatus(termCode, crnList, sis) {},
+    };
+    
\ No newline at end of file
diff --git a/testdata/baselines/reference/compiler/nilPointerInConditionalFlowType.js b/testdata/baselines/reference/compiler/nilPointerInConditionalFlowType.js
new file mode 100644
index 0000000000..98b3e1ea69
--- /dev/null
+++ b/testdata/baselines/reference/compiler/nilPointerInConditionalFlowType.js
@@ -0,0 +1,52 @@
+//// [tests/cases/compiler/nilPointerInConditionalFlowType.ts] ////
+
+//// [test.js]
+const foo = {
+	/**
+	 * @overload
+	 * @param {string} termCode
+	 * @param {string[]} crnList
+	 * @param {string} sis
+	 * @returns {Record<string, string>}
+	 */
+	/**
+	 * @overload
+	 * @param {string} termCode
+	 * @param {string} crn
+	 * @param {string} sis
+	 * @returns {string}
+	 */
+	/**
+	 * @param {string} termCode
+	 * @param {string | string[]} crnList
+	 * @param {string} sis
+	 * @returns {string | Record<string, string>}
+	 */
+	getStatus(termCode, crnList, sis) {},
+};
+
+
+//// [test.js]
+const foo = {
+    /**
+     * @overload
+     * @param {string} termCode
+     * @param {string[]} crnList
+     * @param {string} sis
+     * @returns {Record<string, string>}
+     */
+    /**
+     * @overload
+     * @param {string} termCode
+     * @param {string} crn
+     * @param {string} sis
+     * @returns {string}
+     */
+    /**
+     * @param {string} termCode
+     * @param {string | string[]} crnList
+     * @param {string} sis
+     * @returns {string | Record<string, string>}
+     */
+    getStatus(termCode, crnList, sis) { },
+};
diff --git a/testdata/baselines/reference/compiler/nilPointerInConditionalFlowType.symbols b/testdata/baselines/reference/compiler/nilPointerInConditionalFlowType.symbols
new file mode 100644
index 0000000000..2ba96007cb
--- /dev/null
+++ b/testdata/baselines/reference/compiler/nilPointerInConditionalFlowType.symbols
@@ -0,0 +1,34 @@
+//// [tests/cases/compiler/nilPointerInConditionalFlowType.ts] ////
+
+=== test.js ===
+const foo = {
+>foo : Symbol(foo, Decl(test.js, 0, 5))
+
+	/**
+	 * @overload
+	 * @param {string} termCode
+	 * @param {string[]} crnList
+	 * @param {string} sis
+	 * @returns {Record<string, string>}
+	 */
+	/**
+	 * @overload
+	 * @param {string} termCode
+	 * @param {string} crn
+	 * @param {string} sis
+	 * @returns {string}
+	 */
+	/**
+	 * @param {string} termCode
+	 * @param {string | string[]} crnList
+	 * @param {string} sis
+	 * @returns {string | Record<string, string>}
+	 */
+	getStatus(termCode, crnList, sis) {},
+>getStatus : Symbol(getStatus, Decl(test.js, 0, 13))
+>termCode : Symbol(termCode, Decl(test.js, 21, 11))
+>crnList : Symbol(crnList, Decl(test.js, 21, 20))
+>sis : Symbol(sis, Decl(test.js, 21, 29))
+
+};
+
diff --git a/testdata/baselines/reference/compiler/nilPointerInConditionalFlowType.types b/testdata/baselines/reference/compiler/nilPointerInConditionalFlowType.types
new file mode 100644
index 0000000000..2a5ea8ff75
--- /dev/null
+++ b/testdata/baselines/reference/compiler/nilPointerInConditionalFlowType.types
@@ -0,0 +1,35 @@
+//// [tests/cases/compiler/nilPointerInConditionalFlowType.ts] ////
+
+=== test.js ===
+const foo = {
+>foo : { getStatus(termCode: string, crnList: string | string[], sis: string): string | Record<string, string>; }
+>{	/**	 * @overload	 * @param {string} termCode	 * @param {string[]} crnList	 * @param {string} sis	 * @returns {Record<string, string>}	 */	/**	 * @overload	 * @param {string} termCode	 * @param {string} crn	 * @param {string} sis	 * @returns {string}	 */	/**	 * @param {string} termCode	 * @param {string | string[]} crnList	 * @param {string} sis	 * @returns {string | Record<string, string>}	 */	getStatus(termCode, crnList, sis) {},} : { getStatus(termCode: string, crnList: string | string[], sis: string): string | Record<string, string>; }
+
+	/**
+	 * @overload
+	 * @param {string} termCode
+	 * @param {string[]} crnList
+	 * @param {string} sis
+	 * @returns {Record<string, string>}
+	 */
+	/**
+	 * @overload
+	 * @param {string} termCode
+	 * @param {string} crn
+	 * @param {string} sis
+	 * @returns {string}
+	 */
+	/**
+	 * @param {string} termCode
+	 * @param {string | string[]} crnList
+	 * @param {string} sis
+	 * @returns {string | Record<string, string>}
+	 */
+	getStatus(termCode, crnList, sis) {},
+>getStatus : (termCode: string, crnList: string | string[], sis: string) => string | Record<string, string>
+>termCode : string
+>crnList : string | string[]
+>sis : string
+
+};
+
diff --git a/testdata/baselines/reference/conformance/jsdocVariadicInOverload.js b/testdata/baselines/reference/conformance/jsdocVariadicInOverload.js
index 590e070ce7..f38bc12a54 100644
--- a/testdata/baselines/reference/conformance/jsdocVariadicInOverload.js
+++ b/testdata/baselines/reference/conformance/jsdocVariadicInOverload.js
@@ -131,27 +131,6 @@ export declare class Processor<ParseTree extends Node | undefined = undefined, H
      * @returns {Processor<ParseTree, HeadTree, TailTree, CompileTree, CompileResult>}
      *   Current processor.
      */
-    use(preset?: string | null | undefined): Processor<ParseTree, HeadTree, TailTree, CompileTree, CompileResult>;
-    /**
-     * @overload
-     * @param {string | null | undefined} [preset]
-     * @returns {Processor<ParseTree, HeadTree, TailTree, CompileTree, CompileResult>}
-     *
-     * @template {Array<unknown>} [Parameters=[]]
-     * @template {Node | string | undefined} [Input=undefined]
-     * @template [Output=Input]
-     * @overload
-     * @param {number} plugin
-     * @param {...(Parameters | [boolean])} parameters
-     * @returns {Processor}
-     *
-     * @param {string | number | boolean | null | undefined} value
-     *   Usable value.
-     * @param {...unknown} parameters
-     *   Parameters, when a plugin is given as a usable value.
-     * @returns {Processor<ParseTree, HeadTree, TailTree, CompileTree, CompileResult>}
-     *   Current processor.
-     */
-    use<Parameters extends Array<unknown> = [], Input extends Node | string | undefined = undefined, Output = Input>(plugin: number, ...parameters: (Parameters | [boolean])): Processor;
+    use(value: string | number | boolean | null | undefined, ...parameters: unknown[]): Processor<ParseTree, HeadTree, TailTree, CompileTree, CompileResult>;
 }
 export {};
diff --git a/testdata/baselines/reference/conformance/jsdocVariadicInOverload.symbols b/testdata/baselines/reference/conformance/jsdocVariadicInOverload.symbols
index 6451fe0acb..ba88191eb6 100644
--- a/testdata/baselines/reference/conformance/jsdocVariadicInOverload.symbols
+++ b/testdata/baselines/reference/conformance/jsdocVariadicInOverload.symbols
@@ -41,7 +41,7 @@ export class Processor {
    *   Current processor.
    */
   use(value, ...parameters) {
->use : Symbol(Processor.use, Decl(typeTagForMultipleVariableDeclarations.js, 16, 6), Decl(typeTagForMultipleVariableDeclarations.js, 23, 6), Decl(typeTagForMultipleVariableDeclarations.js, 14, 24))
+>use : Symbol(Processor.use, Decl(typeTagForMultipleVariableDeclarations.js, 14, 24))
 >value : Symbol(value, Decl(typeTagForMultipleVariableDeclarations.js, 35, 6))
 >parameters : Symbol(parameters, Decl(typeTagForMultipleVariableDeclarations.js, 35, 12))
 
@@ -59,9 +59,9 @@ var x = 1, y = 2, z = 3;
 >z : Symbol(z, Decl(typeTagForMultipleVariableDeclarations.js, 40, 17))
 
 p.use(x, y, z);
->p.use : Symbol(Processor.use, Decl(typeTagForMultipleVariableDeclarations.js, 16, 6), Decl(typeTagForMultipleVariableDeclarations.js, 23, 6), Decl(typeTagForMultipleVariableDeclarations.js, 14, 24))
+>p.use : Symbol(Processor.use, Decl(typeTagForMultipleVariableDeclarations.js, 14, 24))
 >p : Symbol(p, Decl(typeTagForMultipleVariableDeclarations.js, 39, 3))
->use : Symbol(Processor.use, Decl(typeTagForMultipleVariableDeclarations.js, 16, 6), Decl(typeTagForMultipleVariableDeclarations.js, 23, 6), Decl(typeTagForMultipleVariableDeclarations.js, 14, 24))
+>use : Symbol(Processor.use, Decl(typeTagForMultipleVariableDeclarations.js, 14, 24))
 >x : Symbol(x, Decl(typeTagForMultipleVariableDeclarations.js, 40, 3))
 >y : Symbol(y, Decl(typeTagForMultipleVariableDeclarations.js, 40, 10))
 >z : Symbol(z, Decl(typeTagForMultipleVariableDeclarations.js, 40, 17))
diff --git a/testdata/baselines/reference/conformance/jsdocVariadicInOverload.types b/testdata/baselines/reference/conformance/jsdocVariadicInOverload.types
index 4a6d237327..2e1662d18e 100644
--- a/testdata/baselines/reference/conformance/jsdocVariadicInOverload.types
+++ b/testdata/baselines/reference/conformance/jsdocVariadicInOverload.types
@@ -41,7 +41,7 @@ export class Processor {
    *   Current processor.
    */
   use(value, ...parameters) {
->use : { (preset?: string): Processor<ParseTree, HeadTree, TailTree, CompileTree, CompileResult>; <Parameters extends unknown[] = [], Input extends string | Node = undefined, Output = Input>(plugin: number, ...parameters: Parameters | [boolean]): Processor<undefined, undefined, undefined, undefined, undefined>; }
+>use : (value: string | number | boolean, ...parameters: unknown[]) => Processor<ParseTree, HeadTree, TailTree, CompileTree, CompileResult>
 >value : string | number | boolean
 >parameters : unknown[]
 
@@ -64,9 +64,9 @@ var x = 1, y = 2, z = 3;
 
 p.use(x, y, z);
 >p.use(x, y, z) : Processor<undefined, undefined, undefined, undefined, undefined>
->p.use : { (preset?: string): Processor<undefined, undefined, undefined, undefined, undefined>; <Parameters extends unknown[] = [], Input extends string | Node = undefined, Output = Input>(plugin: number, ...parameters: Parameters | [boolean]): Processor<undefined, undefined, undefined, undefined, undefined>; }
+>p.use : (value: string | number | boolean, ...parameters: unknown[]) => Processor<undefined, undefined, undefined, undefined, undefined>
 >p : Processor<undefined, undefined, undefined, undefined, undefined>
->use : { (preset?: string): Processor<undefined, undefined, undefined, undefined, undefined>; <Parameters extends unknown[] = [], Input extends string | Node = undefined, Output = Input>(plugin: number, ...parameters: Parameters | [boolean]): Processor<undefined, undefined, undefined, undefined, undefined>; }
+>use : (value: string | number | boolean, ...parameters: unknown[]) => Processor<undefined, undefined, undefined, undefined, undefined>
 >x : number
 >y : number
 >z : number
diff --git a/testdata/baselines/reference/submodule/compiler/jsFileAlternativeUseOfOverloadTag.js b/testdata/baselines/reference/submodule/compiler/jsFileAlternativeUseOfOverloadTag.js
index ebe7145997..a33418fdbf 100644
--- a/testdata/baselines/reference/submodule/compiler/jsFileAlternativeUseOfOverloadTag.js
+++ b/testdata/baselines/reference/submodule/compiler/jsFileAlternativeUseOfOverloadTag.js
@@ -106,7 +106,6 @@ const example3 = {
 
 
 //// [jsFileAlternativeUseOfOverloadTag.d.ts]
-declare function Example1(value: any): any;
 declare const example1: {
     /**
      * @overload Example1(value)
@@ -115,8 +114,6 @@ declare const example1: {
      */
     constructor: (value: any, options: any) => void;
 };
-declare function Example2(value: any, secretAccessKey: any, sessionToken: any): any;
-declare function Example2(): any;
 declare const example2: {
     /**
      * Example 2
@@ -138,7 +135,6 @@ declare const example2: {
      */
     constructor: () => void;
 };
-declare function evaluate(): any;
 type callback = (error: any, result: any) => any;
 declare const example3: {
     /**
diff --git a/testdata/baselines/reference/submodule/compiler/jsFileAlternativeUseOfOverloadTag.js.diff b/testdata/baselines/reference/submodule/compiler/jsFileAlternativeUseOfOverloadTag.js.diff
index f2d21bc5a2..a7fb84a241 100644
--- a/testdata/baselines/reference/submodule/compiler/jsFileAlternativeUseOfOverloadTag.js.diff
+++ b/testdata/baselines/reference/submodule/compiler/jsFileAlternativeUseOfOverloadTag.js.diff
@@ -5,7 +5,6 @@
 
  //// [jsFileAlternativeUseOfOverloadTag.d.ts]
 -declare namespace example1 {
-+declare function Example1(value: any): any;
 +declare const example1: {
      /**
       * @overload Example1(value)
@@ -58,8 +57,6 @@
 -declare namespace example3 {
 +    constructor: (value: any, options: any) => void;
 +};
-+declare function Example2(value: any, secretAccessKey: any, sessionToken: any): any;
-+declare function Example2(): any;
 +declare const example2: {
 +    /**
 +     * Example 2
@@ -81,13 +78,12 @@
 +     */
 +    constructor: () => void;
 +};
-+declare function evaluate(): any;
 +type callback = (error: any, result: any) => any;
 +declare const example3: {
      /**
       * @overload evaluate(options = {}, [callback])
       *   Evaluate something
-@@= skipped -63, +48 lines =@@
+@@= skipped -63, +44 lines =@@
       *     @param result [String]
       *   @see callback
       */
diff --git a/testdata/baselines/reference/submodule/conformance/overloadTag2.errors.txt b/testdata/baselines/reference/submodule/conformance/overloadTag2.errors.txt
index c45c97b5eb..eb5e2e1931 100644
--- a/testdata/baselines/reference/submodule/conformance/overloadTag2.errors.txt
+++ b/testdata/baselines/reference/submodule/conformance/overloadTag2.errors.txt
@@ -1,9 +1,10 @@
-overloadTag2.js(14,9): error TS2394: This overload signature is not compatible with its implementation signature.
 overloadTag2.js(25,20): error TS7006: Parameter 'b' implicitly has an 'any' type.
-overloadTag2.js(30,9): error TS2554: Expected 1-2 arguments, but got 0.
+overloadTag2.js(30,9): error TS2554: Expected 2 arguments, but got 0.
+overloadTag2.js(31,9): error TS2554: Expected 2 arguments, but got 1.
+overloadTag2.js(32,9): error TS2554: Expected 2 arguments, but got 1.
 
 
-==== overloadTag2.js (3 errors) ====
+==== overloadTag2.js (4 errors) ====
     export class Foo {
         #a = true ? 1 : "1"
         #b
@@ -18,9 +19,6 @@ overloadTag2.js(30,9): error TS2554: Expected 1-2 arguments, but got 0.
         /**
          * @constructor
          * @overload
-            ~~~~~~~~
-!!! error TS2394: This overload signature is not compatible with its implementation signature.
-!!! related TS2750 overloadTag2.js:25:5: The implementation signature is declared here.
          * @param {number} a
          */
         /**
@@ -40,9 +38,15 @@ overloadTag2.js(30,9): error TS2554: Expected 1-2 arguments, but got 0.
     }
     var a = new Foo()
             ~~~~~~~~~
-!!! error TS2554: Expected 1-2 arguments, but got 0.
-!!! related TS6210 overloadTag2.js:15:8: An argument for 'a' was not provided.
+!!! error TS2554: Expected 2 arguments, but got 0.
+!!! related TS6210 overloadTag2.js:25:17: An argument for 'a' was not provided.
     var b = new Foo('str')
+            ~~~~~~~~~~~~~~
+!!! error TS2554: Expected 2 arguments, but got 1.
+!!! related TS6210 overloadTag2.js:25:20: An argument for 'b' was not provided.
     var c = new Foo(2)
+            ~~~~~~~~~~
+!!! error TS2554: Expected 2 arguments, but got 1.
+!!! related TS6210 overloadTag2.js:25:20: An argument for 'b' was not provided.
     var d = new Foo('str', 2)
     
\ No newline at end of file
diff --git a/testdata/baselines/reference/submodule/conformance/overloadTag2.errors.txt.diff b/testdata/baselines/reference/submodule/conformance/overloadTag2.errors.txt.diff
new file mode 100644
index 0000000000..a3507ee872
--- /dev/null
+++ b/testdata/baselines/reference/submodule/conformance/overloadTag2.errors.txt.diff
@@ -0,0 +1,46 @@
+--- old.overloadTag2.errors.txt
++++ new.overloadTag2.errors.txt
+@@= skipped -0, +0 lines =@@
+-overloadTag2.js(14,9): error TS2394: This overload signature is not compatible with its implementation signature.
+ overloadTag2.js(25,20): error TS7006: Parameter 'b' implicitly has an 'any' type.
+-overloadTag2.js(30,9): error TS2554: Expected 1-2 arguments, but got 0.
+-
+-
+-==== overloadTag2.js (3 errors) ====
++overloadTag2.js(30,9): error TS2554: Expected 2 arguments, but got 0.
++overloadTag2.js(31,9): error TS2554: Expected 2 arguments, but got 1.
++overloadTag2.js(32,9): error TS2554: Expected 2 arguments, but got 1.
++
++
++==== overloadTag2.js (4 errors) ====
+     export class Foo {
+         #a = true ? 1 : "1"
+         #b
+@@= skipped -17, +18 lines =@@
+         /**
+          * @constructor
+          * @overload
+-            ~~~~~~~~
+-!!! error TS2394: This overload signature is not compatible with its implementation signature.
+-!!! related TS2750 overloadTag2.js:25:5: The implementation signature is declared here.
+          * @param {number} a
+          */
+         /**
+@@= skipped -22, +19 lines =@@
+     }
+     var a = new Foo()
+             ~~~~~~~~~
+-!!! error TS2554: Expected 1-2 arguments, but got 0.
+-!!! related TS6210 overloadTag2.js:15:8: An argument for 'a' was not provided.
++!!! error TS2554: Expected 2 arguments, but got 0.
++!!! related TS6210 overloadTag2.js:25:17: An argument for 'a' was not provided.
+     var b = new Foo('str')
++            ~~~~~~~~~~~~~~
++!!! error TS2554: Expected 2 arguments, but got 1.
++!!! related TS6210 overloadTag2.js:25:20: An argument for 'b' was not provided.
+     var c = new Foo(2)
++            ~~~~~~~~~~
++!!! error TS2554: Expected 2 arguments, but got 1.
++!!! related TS6210 overloadTag2.js:25:20: An argument for 'b' was not provided.
+     var d = new Foo('str', 2)
+     
\ No newline at end of file
diff --git a/testdata/baselines/reference/submodule/conformance/overloadTag2.js b/testdata/baselines/reference/submodule/conformance/overloadTag2.js
index 8e03c4882c..79aec3b329 100644
--- a/testdata/baselines/reference/submodule/conformance/overloadTag2.js
+++ b/testdata/baselines/reference/submodule/conformance/overloadTag2.js
@@ -74,7 +74,25 @@ var d = new Foo('str', 2);
 //// [overloadTag2.d.ts]
 export declare class Foo {
     #private;
-    constructor(a: string, b: number);
-    constructor(a: number);
-    constructor(a: string);
+    /**
+     * Should not have an implicit any error, because constructor's return type is always implicit
+     * @constructor
+     * @overload
+     * @param {string} a
+     * @param {number} b
+     */
+    /**
+     * @constructor
+     * @overload
+     * @param {number} a
+     */
+    /**
+     * @constructor
+     * @overload
+     * @param {string} a
+     */ /**
+    * @constructor
+    * @param {number | string} a
+    */
+    constructor(a: number | string, b: any);
 }
diff --git a/testdata/baselines/reference/submodule/conformance/overloadTag2.js.diff b/testdata/baselines/reference/submodule/conformance/overloadTag2.js.diff
index cdc90d2751..3e7fb1e487 100644
--- a/testdata/baselines/reference/submodule/conformance/overloadTag2.js.diff
+++ b/testdata/baselines/reference/submodule/conformance/overloadTag2.js.diff
@@ -5,27 +5,32 @@
 
  //// [overloadTag2.d.ts]
 -export class Foo {
--    /**
--     * Should not have an implicit any error, because constructor's return type is always implicit
--     * @constructor
--     * @overload
--     * @param {string} a
--     * @param {number} b
--     */
 +export declare class Foo {
 +    #private;
-     constructor(a: string, b: number);
--    /**
--     * @constructor
--     * @overload
--     * @param {number} a
--     */
-     constructor(a: number);
--    /**
--     * @constructor
--     * @overload
--     * @param {string} a
+     /**
+      * Should not have an implicit any error, because constructor's return type is always implicit
+      * @constructor
+@@= skipped -8, +9 lines =@@
+      * @param {string} a
+      * @param {number} b
+      */
+-    constructor(a: string, b: number);
+     /**
+      * @constructor
+      * @overload
+      * @param {number} a
+      */
+-    constructor(a: number);
+     /**
+      * @constructor
+      * @overload
+      * @param {string} a
 -     */
-     constructor(a: string);
+-    constructor(a: string);
 -    #private;
++     */ /**
++    * @constructor
++    * @param {number | string} a
++    */
++    constructor(a: number | string, b: any);
  }
\ No newline at end of file
diff --git a/testdata/tests/cases/compiler/nilPointerInConditionalFlowType.ts b/testdata/tests/cases/compiler/nilPointerInConditionalFlowType.ts
new file mode 100644
index 0000000000..b78007ac41
--- /dev/null
+++ b/testdata/tests/cases/compiler/nilPointerInConditionalFlowType.ts
@@ -0,0 +1,28 @@
+// @allowJs: true
+// @checkJs: true
+// @outDir: ./out
+// @filename: test.js
+
+const foo = {
+	/**
+	 * @overload
+	 * @param {string} termCode
+	 * @param {string[]} crnList
+	 * @param {string} sis
+	 * @returns {Record<string, string>}
+	 */
+	/**
+	 * @overload
+	 * @param {string} termCode
+	 * @param {string} crn
+	 * @param {string} sis
+	 * @returns {string}
+	 */
+	/**
+	 * @param {string} termCode
+	 * @param {string | string[]} crnList
+	 * @param {string} sis
+	 * @returns {string | Record<string, string>}
+	 */
+	getStatus(termCode, crnList, sis) {},
+};