diff --git a/src/compiler/commandLineParser.ts b/src/compiler/commandLineParser.ts
index f44eae9455f..99770a75aee 100644
--- a/src/compiler/commandLineParser.ts
+++ b/src/compiler/commandLineParser.ts
@@ -1603,7 +1603,7 @@ namespace ts {
     export function parseConfigFileTextToJson(fileName: string, jsonText: string): { config?: any; error?: Diagnostic } {
         const jsonSourceFile = parseJsonText(fileName, jsonText);
         return {
-            config: convertToObject(jsonSourceFile, jsonSourceFile.parseDiagnostics),
+            config: convertConfigFileToObject(jsonSourceFile, jsonSourceFile.parseDiagnostics, /*reportOptionsErrors*/ false, /*optionsIterator*/ undefined),
             error: jsonSourceFile.parseDiagnostics.length ? jsonSourceFile.parseDiagnostics[0] : undefined
         };
     }
@@ -1767,11 +1767,35 @@ namespace ts {
         onSetUnknownOptionKeyValueInRoot(key: string, keyNode: PropertyName, value: CompilerOptionsValue, valueNode: Expression): void;
     }
 
+    function convertConfigFileToObject(sourceFile: JsonSourceFile, errors: Push<Diagnostic>, reportOptionsErrors: boolean, optionsIterator: JsonConversionNotifier | undefined): any {
+        const rootExpression: Expression | undefined = sourceFile.statements[0]?.expression;
+        const knownRootOptions = reportOptionsErrors ? getTsconfigRootOptionsMap() : undefined;
+        if (rootExpression && rootExpression.kind !== SyntaxKind.ObjectLiteralExpression) {
+            errors.push(createDiagnosticForNodeInSourceFile(
+                sourceFile,
+                rootExpression,
+                Diagnostics.The_root_value_of_a_0_file_must_be_an_object,
+                getBaseFileName(sourceFile.fileName) === "jsconfig.json" ? "jsconfig.json" : "tsconfig.json"
+            ));
+            // Last-ditch error recovery. Somewhat useful because the JSON parser will recover from some parse errors by
+            // synthesizing a top-level array literal expression. There's a reasonable chance the first element of that
+            // array is a well-formed configuration object, made into an array element by stray characters.
+            if (isArrayLiteralExpression(rootExpression)) {
+                const firstObject = find(rootExpression.elements, isObjectLiteralExpression);
+                if (firstObject) {
+                    return convertToObjectWorker(sourceFile, firstObject, errors, /*returnValue*/ true, knownRootOptions, optionsIterator);
+                }
+            }
+            return {};
+        }
+        return convertToObjectWorker(sourceFile, rootExpression, errors, /*returnValue*/ true, knownRootOptions, optionsIterator);
+    }
+
     /**
      * Convert the json syntax tree into the json value
      */
     export function convertToObject(sourceFile: JsonSourceFile, errors: Push<Diagnostic>): any {
-        return convertToObjectWorker(sourceFile, errors, /*returnValue*/ true, /*knownRootOptions*/ undefined, /*jsonConversionNotifier*/ undefined);
+        return convertToObjectWorker(sourceFile, sourceFile.statements[0]?.expression, errors, /*returnValue*/ true, /*knownRootOptions*/ undefined, /*jsonConversionNotifier*/ undefined);
     }
 
     /**
@@ -1782,15 +1806,16 @@ namespace ts {
     /*@internal*/
     export function convertToObjectWorker(
         sourceFile: JsonSourceFile,
+        rootExpression: Expression | undefined,
         errors: Push<Diagnostic>,
         returnValue: boolean,
         knownRootOptions: CommandLineOption | undefined,
         jsonConversionNotifier: JsonConversionNotifier | undefined): any {
-        if (!sourceFile.statements.length) {
+        if (!rootExpression) {
             return returnValue ? {} : undefined;
         }
 
-        return convertPropertyValueToJson(sourceFile.statements[0].expression, knownRootOptions);
+        return convertPropertyValueToJson(rootExpression, knownRootOptions);
 
         function isRootOptionMap(knownOptions: ESMap<string, CommandLineOption> | undefined) {
             return knownRootOptions && (knownRootOptions as TsConfigOnlyOption).elementOptions === knownOptions;
@@ -2733,7 +2758,7 @@ namespace ts {
                 }
             }
         };
-        const json = convertToObjectWorker(sourceFile, errors, /*returnValue*/ true, getTsconfigRootOptionsMap(), optionsIterator);
+        const json = convertConfigFileToObject(sourceFile, errors, /*reportOptionsErrors*/ true, optionsIterator);
 
         if (!typeAcquisition) {
             if (typingOptionstypeAcquisition) {
diff --git a/src/compiler/diagnosticMessages.json b/src/compiler/diagnosticMessages.json
index bda4c727373..b23bfbf7ea4 100644
--- a/src/compiler/diagnosticMessages.json
+++ b/src/compiler/diagnosticMessages.json
@@ -3850,6 +3850,10 @@
         "category": "Error",
         "code": 5091
     },
+    "The root value of a '{0}' file must be an object.": {
+        "category": "Error",
+        "code": 5092
+    },
 
     "Generates a sourcemap for each corresponding '.d.ts' file.": {
         "category": "Message",
diff --git a/src/compiler/parser.ts b/src/compiler/parser.ts
index a7fac539da5..01f42d64917 100644
--- a/src/compiler/parser.ts
+++ b/src/compiler/parser.ts
@@ -819,7 +819,7 @@ namespace ts {
             scriptKind = ensureScriptKind(fileName, scriptKind);
             if (scriptKind === ScriptKind.JSON) {
                 const result = parseJsonText(fileName, sourceText, languageVersion, syntaxCursor, setParentNodes);
-                convertToObjectWorker(result, result.parseDiagnostics, /*returnValue*/ false, /*knownRootOptions*/ undefined, /*jsonConversionNotifier*/ undefined);
+                convertToObjectWorker(result, result.statements[0]?.expression, result.parseDiagnostics, /*returnValue*/ false, /*knownRootOptions*/ undefined, /*jsonConversionNotifier*/ undefined);
                 result.referencedFiles = emptyArray;
                 result.typeReferenceDirectives = emptyArray;
                 result.libReferenceDirectives = emptyArray;
@@ -862,36 +862,56 @@ namespace ts {
                 endOfFileToken = parseTokenNode<EndOfFileToken>();
             }
             else {
-                let expression;
-                switch (token()) {
-                    case SyntaxKind.OpenBracketToken:
-                        expression = parseArrayLiteralExpression();
-                        break;
-                    case SyntaxKind.TrueKeyword:
-                    case SyntaxKind.FalseKeyword:
-                    case SyntaxKind.NullKeyword:
-                        expression = parseTokenNode<BooleanLiteral | NullLiteral>();
-                        break;
-                    case SyntaxKind.MinusToken:
-                        if (lookAhead(() => nextToken() === SyntaxKind.NumericLiteral && nextToken() !== SyntaxKind.ColonToken)) {
-                            expression = parsePrefixUnaryExpression() as JsonMinusNumericLiteral;
-                        }
-                        else {
-                            expression = parseObjectLiteralExpression();
-                        }
-                        break;
-                    case SyntaxKind.NumericLiteral:
-                    case SyntaxKind.StringLiteral:
-                        if (lookAhead(() => nextToken() !== SyntaxKind.ColonToken)) {
-                            expression = parseLiteralNode() as StringLiteral | NumericLiteral;
+                // Loop and synthesize an ArrayLiteralExpression if there are more than
+                // one top-level expressions to ensure all input text is consumed.
+                let expressions: Expression[] | Expression | undefined;
+                while (token() !== SyntaxKind.EndOfFileToken) {
+                    let expression;
+                    switch (token()) {
+                        case SyntaxKind.OpenBracketToken:
+                            expression = parseArrayLiteralExpression();
                             break;
+                        case SyntaxKind.TrueKeyword:
+                        case SyntaxKind.FalseKeyword:
+                        case SyntaxKind.NullKeyword:
+                            expression = parseTokenNode<BooleanLiteral | NullLiteral>();
+                            break;
+                        case SyntaxKind.MinusToken:
+                            if (lookAhead(() => nextToken() === SyntaxKind.NumericLiteral && nextToken() !== SyntaxKind.ColonToken)) {
+                                expression = parsePrefixUnaryExpression() as JsonMinusNumericLiteral;
+                            }
+                            else {
+                                expression = parseObjectLiteralExpression();
+                            }
+                            break;
+                        case SyntaxKind.NumericLiteral:
+                        case SyntaxKind.StringLiteral:
+                            if (lookAhead(() => nextToken() !== SyntaxKind.ColonToken)) {
+                                expression = parseLiteralNode() as StringLiteral | NumericLiteral;
+                                break;
+                            }
+                            // falls through
+                        default:
+                            expression = parseObjectLiteralExpression();
+                            break;
+                    }
+
+                    // Error recovery: collect multiple top-level expressions
+                    if (expressions && isArray(expressions)) {
+                        expressions.push(expression);
+                    }
+                    else if (expressions) {
+                        expressions = [expressions, expression];
+                    }
+                    else {
+                        expressions = expression;
+                        if (token() !== SyntaxKind.EndOfFileToken) {
+                            parseErrorAtCurrentToken(Diagnostics.Unexpected_token);
                         }
-                        // falls through
-                    default:
-                        expression = parseObjectLiteralExpression();
-                        break;
+                    }
                 }
 
+                const expression = isArray(expressions) ? finishNode(factory.createArrayLiteralExpression(expressions), pos) : Debug.checkDefined(expressions);
                 const statement = factory.createExpressionStatement(expression) as JsonObjectExpressionStatement;
                 finishNode(statement, pos);
                 statements = createNodeArray([statement], pos);
diff --git a/src/testRunner/tsconfig.json b/src/testRunner/tsconfig.json
index a1985566b92..91691b6d4b5 100644
--- a/src/testRunner/tsconfig.json
+++ b/src/testRunner/tsconfig.json
@@ -66,6 +66,7 @@
         "unittests/factory.ts",
         "unittests/incrementalParser.ts",
         "unittests/jsDocParsing.ts",
+        "unittests/jsonParserRecovery.ts",
         "unittests/moduleResolution.ts",
         "unittests/parsePseudoBigInt.ts",
         "unittests/paths.ts",
diff --git a/src/testRunner/unittests/config/convertCompilerOptionsFromJson.ts b/src/testRunner/unittests/config/convertCompilerOptionsFromJson.ts
index d007ccf5f84..71c826351d0 100644
--- a/src/testRunner/unittests/config/convertCompilerOptionsFromJson.ts
+++ b/src/testRunner/unittests/config/convertCompilerOptionsFromJson.ts
@@ -69,7 +69,7 @@ namespace ts {
                 assert.equal(actualError.category, expectedError.category, `Expected error-category: ${JSON.stringify(expectedError.category)}. Actual error-category: ${JSON.stringify(actualError.category)}.`);
                 if (!ignoreLocation) {
                     assert(actualError.file);
-                    assert(actualError.start);
+                    assert.isDefined(actualError.start);
                     assert(actualError.length);
                 }
             }
@@ -603,5 +603,84 @@ namespace ts {
                 hasParseErrors: true
             });
         });
+
+        it("Convert a tsconfig file with stray trailing characters", () => {
+            assertCompilerOptionsWithJsonText(`{
+                "compilerOptions": {
+                    "target": "esnext"
+                }
+            } blah`, "tsconfig.json", {
+                compilerOptions: {
+                    target: ScriptTarget.ESNext
+                },
+                hasParseErrors: true,
+                errors: [{
+                    ...Diagnostics.The_root_value_of_a_0_file_must_be_an_object,
+                    messageText: "The root value of a 'tsconfig.json' file must be an object.",
+                    file: undefined,
+                    start: 0,
+                    length: 0
+                }]
+            });
+        });
+
+        it("Convert a tsconfig file with stray leading characters", () => {
+            assertCompilerOptionsWithJsonText(`blah {
+                "compilerOptions": {
+                    "target": "esnext"
+                }
+            }`, "tsconfig.json", {
+                compilerOptions: {
+                    target: ScriptTarget.ESNext
+                },
+                hasParseErrors: true,
+                errors: [{
+                    ...Diagnostics.The_root_value_of_a_0_file_must_be_an_object,
+                    messageText: "The root value of a 'tsconfig.json' file must be an object.",
+                    file: undefined,
+                    start: 0,
+                    length: 0
+                }]
+            });
+        });
+
+        it("Convert a tsconfig file as an array", () => {
+            assertCompilerOptionsWithJsonText(`[{
+                "compilerOptions": {
+                    "target": "esnext"
+                }
+            }]`, "tsconfig.json", {
+                compilerOptions: {
+                    target: ScriptTarget.ESNext
+                },
+                errors: [{
+                    ...Diagnostics.The_root_value_of_a_0_file_must_be_an_object,
+                    messageText: "The root value of a 'tsconfig.json' file must be an object.",
+                    file: undefined,
+                    start: 0,
+                    length: 0
+                }]
+            });
+        });
+
+        it("Don't crash when root expression is not objecty at all", () => {
+            assertCompilerOptionsWithJsonText(`42`, "tsconfig.json", {
+                compilerOptions: {},
+                errors: [{
+                    ...Diagnostics.The_root_value_of_a_0_file_must_be_an_object,
+                    messageText: "The root value of a 'tsconfig.json' file must be an object.",
+                    file: undefined,
+                    start: 0,
+                    length: 0
+                }]
+            });
+        });
+
+        it("Allow trailing comments", () => {
+            assertCompilerOptionsWithJsonText(`{} // no options`, "tsconfig.json", {
+                compilerOptions: {},
+                errors: []
+            });
+        });
     });
 }
diff --git a/src/testRunner/unittests/jsonParserRecovery.ts b/src/testRunner/unittests/jsonParserRecovery.ts
new file mode 100644
index 00000000000..43007a687d3
--- /dev/null
+++ b/src/testRunner/unittests/jsonParserRecovery.ts
@@ -0,0 +1,39 @@
+namespace ts {
+    describe("unittests:: jsonParserRecovery", () => {
+        function parsesToValidSourceFileWithErrors(name: string, text: string) {
+            it(name, () => {
+                const file = parseJsonText(name, text);
+                assert(file.parseDiagnostics.length, "Should have parse errors");
+                Harness.Baseline.runBaseline(
+                    `jsonParserRecovery/${name.replace(/[^a-z0-9_-]/ig, "_")}.errors.txt`,
+                    Harness.Compiler.getErrorBaseline([{
+                        content: text,
+                        unitName: name
+                    }], file.parseDiagnostics));
+
+                // Will throw if parse tree does not cover full input text
+                file.getChildren();
+            });
+        }
+
+        parsesToValidSourceFileWithErrors("trailing identifier", "{} blah");
+        parsesToValidSourceFileWithErrors("TypeScript code", "interface Foo {} blah");
+        parsesToValidSourceFileWithErrors("Two comma-separated objects", "{}, {}");
+        parsesToValidSourceFileWithErrors("Two objects", "{} {}");
+        parsesToValidSourceFileWithErrors("JSX", `
+        interface Test {}
+
+        const Header = () => (
+          <div>
+            <h1>Header</h1>
+            <style jsx>
+              {\`
+                h1 {
+                  color: red;
+                }
+              \`}
+            </style>
+          </div>
+        )`);
+    });
+}
diff --git a/tests/baselines/reference/jsonParserRecovery/JSX.errors.txt b/tests/baselines/reference/jsonParserRecovery/JSX.errors.txt
new file mode 100644
index 00000000000..7789f6c0019
--- /dev/null
+++ b/tests/baselines/reference/jsonParserRecovery/JSX.errors.txt
@@ -0,0 +1,37 @@
+JSX(2,9): error TS1005: '{' expected.
+JSX(2,19): error TS1005: ',' expected.
+JSX(2,24): error TS1005: ',' expected.
+JSX(4,9): error TS1012: Unexpected token.
+JSX(4,15): error TS1005: ':' expected.
+JSX(15,10): error TS1005: '}' expected.
+
+
+==== JSX (6 errors) ====
+    
+            interface Test {}
+            ~~~~~~~~~
+!!! error TS1005: '{' expected.
+                      ~~~~
+!!! error TS1005: ',' expected.
+                           ~
+!!! error TS1005: ',' expected.
+    
+            const Header = () => (
+            ~~~~~
+!!! error TS1012: Unexpected token.
+                  ~~~~~~
+!!! error TS1005: ':' expected.
+              <div>
+                <h1>Header</h1>
+                <style jsx>
+                  {`
+                    h1 {
+                      color: red;
+                    }
+                  `}
+                </style>
+              </div>
+            )
+             
+!!! error TS1005: '}' expected.
+!!! related TS1007 JSX:4:9: The parser expected to find a '}' to match the '{' token here.
\ No newline at end of file
diff --git a/tests/baselines/reference/jsonParserRecovery/Two_comma-separated_objects.errors.txt b/tests/baselines/reference/jsonParserRecovery/Two_comma-separated_objects.errors.txt
new file mode 100644
index 00000000000..08609f53d20
--- /dev/null
+++ b/tests/baselines/reference/jsonParserRecovery/Two_comma-separated_objects.errors.txt
@@ -0,0 +1,10 @@
+Two comma-separated objects(1,3): error TS1012: Unexpected token.
+Two comma-separated objects(1,5): error TS1136: Property assignment expected.
+
+
+==== Two comma-separated objects (2 errors) ====
+    {}, {}
+      ~
+!!! error TS1012: Unexpected token.
+        ~
+!!! error TS1136: Property assignment expected.
\ No newline at end of file
diff --git a/tests/baselines/reference/jsonParserRecovery/Two_objects.errors.txt b/tests/baselines/reference/jsonParserRecovery/Two_objects.errors.txt
new file mode 100644
index 00000000000..e7e7fd329c3
--- /dev/null
+++ b/tests/baselines/reference/jsonParserRecovery/Two_objects.errors.txt
@@ -0,0 +1,7 @@
+Two objects(1,4): error TS1012: Unexpected token.
+
+
+==== Two objects (1 errors) ====
+    {} {}
+       ~
+!!! error TS1012: Unexpected token.
\ No newline at end of file
diff --git a/tests/baselines/reference/jsonParserRecovery/TypeScript_code.errors.txt b/tests/baselines/reference/jsonParserRecovery/TypeScript_code.errors.txt
new file mode 100644
index 00000000000..cd17a0c487e
--- /dev/null
+++ b/tests/baselines/reference/jsonParserRecovery/TypeScript_code.errors.txt
@@ -0,0 +1,20 @@
+TypeScript code(1,1): error TS1005: '{' expected.
+TypeScript code(1,11): error TS1005: ',' expected.
+TypeScript code(1,15): error TS1005: ',' expected.
+TypeScript code(1,18): error TS1012: Unexpected token.
+TypeScript code(1,22): error TS1005: '}' expected.
+
+
+==== TypeScript code (5 errors) ====
+    interface Foo {} blah
+    ~~~~~~~~~
+!!! error TS1005: '{' expected.
+              ~~~
+!!! error TS1005: ',' expected.
+                  ~
+!!! error TS1005: ',' expected.
+                     ~~~~
+!!! error TS1012: Unexpected token.
+                         
+!!! error TS1005: '}' expected.
+!!! related TS1007 TypeScript code:1:18: The parser expected to find a '}' to match the '{' token here.
\ No newline at end of file
diff --git a/tests/baselines/reference/jsonParserRecovery/trailing_identifier.errors.txt b/tests/baselines/reference/jsonParserRecovery/trailing_identifier.errors.txt
new file mode 100644
index 00000000000..11c44b08f00
--- /dev/null
+++ b/tests/baselines/reference/jsonParserRecovery/trailing_identifier.errors.txt
@@ -0,0 +1,11 @@
+trailing identifier(1,4): error TS1012: Unexpected token.
+trailing identifier(1,8): error TS1005: '}' expected.
+
+
+==== trailing identifier (2 errors) ====
+    {} blah
+       ~~~~
+!!! error TS1012: Unexpected token.
+           
+!!! error TS1005: '}' expected.
+!!! related TS1007 trailing identifier:1:4: The parser expected to find a '}' to match the '{' token here.
\ No newline at end of file