diff --git a/src/compiler/checker.ts b/src/compiler/checker.ts
index d825b0d971758..cd4243f8550b3 100644
--- a/src/compiler/checker.ts
+++ b/src/compiler/checker.ts
@@ -14941,7 +14941,7 @@ namespace ts {
                     // except for the special case of Javascript declarations of the form `namespace.prop = namespace.prop || {}`
                     const type = getContextualType(binaryExpression);
                     return !type && node === right && !getDeclaredJavascriptInitializer(binaryExpression.parent) && !getAssignedJavascriptInitializer(binaryExpression) ?
-                        getTypeOfExpression(left, /*cache*/ true) : type;
+                        getTypeOfExpression(left) : type;
                 case SyntaxKind.AmpersandAmpersandToken:
                 case SyntaxKind.CommaToken:
                     return node === right ? getContextualType(binaryExpression) : undefined;
diff --git a/tests/baselines/reference/contextualExpressionTypecheckingDoesntBlowStack.js b/tests/baselines/reference/contextualExpressionTypecheckingDoesntBlowStack.js
new file mode 100644
index 0000000000000..8e600761d2c7f
--- /dev/null
+++ b/tests/baselines/reference/contextualExpressionTypecheckingDoesntBlowStack.js
@@ -0,0 +1,48 @@
+//// [contextualExpressionTypecheckingDoesntBlowStack.ts]
+// repro for: https://github.com/Microsoft/TypeScript/issues/23661
+export interface IValidationError {
+    message: string;
+}
+
+export default class Operation {
+    validateParameters(parameterValues: any) : IValidationError[] | null {
+        let result: IValidationError[] | null = null;
+        for(const parameterLocation of Object.keys(parameterValues)) {
+            const parameter: any = (this as any).getParameter();;
+            const values = (this as any).getValues();
+
+            const innerResult = parameter.validate(values[parameter.oaParameter.name]);
+            if(innerResult && innerResult.length > 0) {
+                // Commenting out this line will fix the problem.
+                result = (result || []).concat(innerResult);
+            }
+        }
+
+        return result;
+    }
+}
+
+//// [contextualExpressionTypecheckingDoesntBlowStack.js]
+"use strict";
+Object.defineProperty(exports, "__esModule", { value: true });
+var Operation = /** @class */ (function () {
+    function Operation() {
+    }
+    Operation.prototype.validateParameters = function (parameterValues) {
+        var result = null;
+        for (var _i = 0, _a = Object.keys(parameterValues); _i < _a.length; _i++) {
+            var parameterLocation = _a[_i];
+            var parameter = this.getParameter();
+            ;
+            var values = this.getValues();
+            var innerResult = parameter.validate(values[parameter.oaParameter.name]);
+            if (innerResult && innerResult.length > 0) {
+                // Commenting out this line will fix the problem.
+                result = (result || []).concat(innerResult);
+            }
+        }
+        return result;
+    };
+    return Operation;
+}());
+exports.default = Operation;
diff --git a/tests/baselines/reference/contextualExpressionTypecheckingDoesntBlowStack.symbols b/tests/baselines/reference/contextualExpressionTypecheckingDoesntBlowStack.symbols
new file mode 100644
index 0000000000000..fc44c97996c92
--- /dev/null
+++ b/tests/baselines/reference/contextualExpressionTypecheckingDoesntBlowStack.symbols
@@ -0,0 +1,60 @@
+=== tests/cases/compiler/contextualExpressionTypecheckingDoesntBlowStack.ts ===
+// repro for: https://github.com/Microsoft/TypeScript/issues/23661
+export interface IValidationError {
+>IValidationError : Symbol(IValidationError, Decl(contextualExpressionTypecheckingDoesntBlowStack.ts, 0, 0))
+
+    message: string;
+>message : Symbol(IValidationError.message, Decl(contextualExpressionTypecheckingDoesntBlowStack.ts, 1, 35))
+}
+
+export default class Operation {
+>Operation : Symbol(Operation, Decl(contextualExpressionTypecheckingDoesntBlowStack.ts, 3, 1))
+
+    validateParameters(parameterValues: any) : IValidationError[] | null {
+>validateParameters : Symbol(Operation.validateParameters, Decl(contextualExpressionTypecheckingDoesntBlowStack.ts, 5, 32))
+>parameterValues : Symbol(parameterValues, Decl(contextualExpressionTypecheckingDoesntBlowStack.ts, 6, 23))
+>IValidationError : Symbol(IValidationError, Decl(contextualExpressionTypecheckingDoesntBlowStack.ts, 0, 0))
+
+        let result: IValidationError[] | null = null;
+>result : Symbol(result, Decl(contextualExpressionTypecheckingDoesntBlowStack.ts, 7, 11))
+>IValidationError : Symbol(IValidationError, Decl(contextualExpressionTypecheckingDoesntBlowStack.ts, 0, 0))
+
+        for(const parameterLocation of Object.keys(parameterValues)) {
+>parameterLocation : Symbol(parameterLocation, Decl(contextualExpressionTypecheckingDoesntBlowStack.ts, 8, 17))
+>Object.keys : Symbol(ObjectConstructor.keys, Decl(lib.es5.d.ts, --, --))
+>Object : Symbol(Object, Decl(lib.es5.d.ts, --, --), Decl(lib.es5.d.ts, --, --))
+>keys : Symbol(ObjectConstructor.keys, Decl(lib.es5.d.ts, --, --))
+>parameterValues : Symbol(parameterValues, Decl(contextualExpressionTypecheckingDoesntBlowStack.ts, 6, 23))
+
+            const parameter: any = (this as any).getParameter();;
+>parameter : Symbol(parameter, Decl(contextualExpressionTypecheckingDoesntBlowStack.ts, 9, 17))
+>this : Symbol(Operation, Decl(contextualExpressionTypecheckingDoesntBlowStack.ts, 3, 1))
+
+            const values = (this as any).getValues();
+>values : Symbol(values, Decl(contextualExpressionTypecheckingDoesntBlowStack.ts, 10, 17))
+>this : Symbol(Operation, Decl(contextualExpressionTypecheckingDoesntBlowStack.ts, 3, 1))
+
+            const innerResult = parameter.validate(values[parameter.oaParameter.name]);
+>innerResult : Symbol(innerResult, Decl(contextualExpressionTypecheckingDoesntBlowStack.ts, 12, 17))
+>parameter : Symbol(parameter, Decl(contextualExpressionTypecheckingDoesntBlowStack.ts, 9, 17))
+>values : Symbol(values, Decl(contextualExpressionTypecheckingDoesntBlowStack.ts, 10, 17))
+>parameter : Symbol(parameter, Decl(contextualExpressionTypecheckingDoesntBlowStack.ts, 9, 17))
+
+            if(innerResult && innerResult.length > 0) {
+>innerResult : Symbol(innerResult, Decl(contextualExpressionTypecheckingDoesntBlowStack.ts, 12, 17))
+>innerResult : Symbol(innerResult, Decl(contextualExpressionTypecheckingDoesntBlowStack.ts, 12, 17))
+
+                // Commenting out this line will fix the problem.
+                result = (result || []).concat(innerResult);
+>result : Symbol(result, Decl(contextualExpressionTypecheckingDoesntBlowStack.ts, 7, 11))
+>(result || []).concat : Symbol(Array.concat, Decl(lib.es5.d.ts, --, --), Decl(lib.es5.d.ts, --, --))
+>result : Symbol(result, Decl(contextualExpressionTypecheckingDoesntBlowStack.ts, 7, 11))
+>concat : Symbol(Array.concat, Decl(lib.es5.d.ts, --, --), Decl(lib.es5.d.ts, --, --))
+>innerResult : Symbol(innerResult, Decl(contextualExpressionTypecheckingDoesntBlowStack.ts, 12, 17))
+            }
+        }
+
+        return result;
+>result : Symbol(result, Decl(contextualExpressionTypecheckingDoesntBlowStack.ts, 7, 11))
+    }
+}
diff --git a/tests/baselines/reference/contextualExpressionTypecheckingDoesntBlowStack.types b/tests/baselines/reference/contextualExpressionTypecheckingDoesntBlowStack.types
new file mode 100644
index 0000000000000..5965a2c77430e
--- /dev/null
+++ b/tests/baselines/reference/contextualExpressionTypecheckingDoesntBlowStack.types
@@ -0,0 +1,92 @@
+=== tests/cases/compiler/contextualExpressionTypecheckingDoesntBlowStack.ts ===
+// repro for: https://github.com/Microsoft/TypeScript/issues/23661
+export interface IValidationError {
+>IValidationError : IValidationError
+
+    message: string;
+>message : string
+}
+
+export default class Operation {
+>Operation : Operation
+
+    validateParameters(parameterValues: any) : IValidationError[] | null {
+>validateParameters : (parameterValues: any) => IValidationError[] | null
+>parameterValues : any
+>IValidationError : IValidationError
+>null : null
+
+        let result: IValidationError[] | null = null;
+>result : IValidationError[] | null
+>IValidationError : IValidationError
+>null : null
+>null : null
+
+        for(const parameterLocation of Object.keys(parameterValues)) {
+>parameterLocation : string
+>Object.keys(parameterValues) : string[]
+>Object.keys : (o: {}) => string[]
+>Object : ObjectConstructor
+>keys : (o: {}) => string[]
+>parameterValues : any
+
+            const parameter: any = (this as any).getParameter();;
+>parameter : any
+>(this as any).getParameter() : any
+>(this as any).getParameter : any
+>(this as any) : any
+>this as any : any
+>this : this
+>getParameter : any
+
+            const values = (this as any).getValues();
+>values : any
+>(this as any).getValues() : any
+>(this as any).getValues : any
+>(this as any) : any
+>this as any : any
+>this : this
+>getValues : any
+
+            const innerResult = parameter.validate(values[parameter.oaParameter.name]);
+>innerResult : any
+>parameter.validate(values[parameter.oaParameter.name]) : any
+>parameter.validate : any
+>parameter : any
+>validate : any
+>values[parameter.oaParameter.name] : any
+>values : any
+>parameter.oaParameter.name : any
+>parameter.oaParameter : any
+>parameter : any
+>oaParameter : any
+>name : any
+
+            if(innerResult && innerResult.length > 0) {
+>innerResult && innerResult.length > 0 : boolean
+>innerResult : any
+>innerResult.length > 0 : boolean
+>innerResult.length : any
+>innerResult : any
+>length : any
+>0 : 0
+
+                // Commenting out this line will fix the problem.
+                result = (result || []).concat(innerResult);
+>result = (result || []).concat(innerResult) : IValidationError[]
+>result : IValidationError[] | null
+>(result || []).concat(innerResult) : IValidationError[]
+>(result || []).concat : { (...items: ConcatArray<IValidationError>[]): IValidationError[]; (...items: (IValidationError | ConcatArray<IValidationError>)[]): IValidationError[]; }
+>(result || []) : IValidationError[]
+>result || [] : IValidationError[]
+>result : IValidationError[] | null
+>[] : never[]
+>concat : { (...items: ConcatArray<IValidationError>[]): IValidationError[]; (...items: (IValidationError | ConcatArray<IValidationError>)[]): IValidationError[]; }
+>innerResult : any
+            }
+        }
+
+        return result;
+>result : IValidationError[] | null
+    }
+}
diff --git a/tests/cases/compiler/contextualExpressionTypecheckingDoesntBlowStack.ts b/tests/cases/compiler/contextualExpressionTypecheckingDoesntBlowStack.ts
new file mode 100644
index 0000000000000..9abff096a7631
--- /dev/null
+++ b/tests/cases/compiler/contextualExpressionTypecheckingDoesntBlowStack.ts
@@ -0,0 +1,26 @@
+// @target: es5
+// @lib: es6
+// @strict: true
+
+// repro for: https://github.com/Microsoft/TypeScript/issues/23661
+export interface IValidationError {
+    message: string;
+}
+
+export default class Operation {
+    validateParameters(parameterValues: any) : IValidationError[] | null {
+        let result: IValidationError[] | null = null;
+        for(const parameterLocation of Object.keys(parameterValues)) {
+            const parameter: any = (this as any).getParameter();;
+            const values = (this as any).getValues();
+
+            const innerResult = parameter.validate(values[parameter.oaParameter.name]);
+            if(innerResult && innerResult.length > 0) {
+                // Commenting out this line will fix the problem.
+                result = (result || []).concat(innerResult);
+            }
+        }
+
+        return result;
+    }
+}
\ No newline at end of file