diff --git a/src/compiler/sys.ts b/src/compiler/sys.ts
index c37315a2e5601..be95e06eb46cb 100644
--- a/src/compiler/sys.ts
+++ b/src/compiler/sys.ts
@@ -428,6 +428,7 @@ namespace ts {
         newLine: string;
         useCaseSensitiveFileNames: boolean;
         write(s: string): void;
+        writeOutputIsTTY?(): boolean;
         readFile(path: string, encoding?: string): string | undefined;
         getFileSize?(path: string): number;
         writeFile(path: string, data: string, writeByteOrderMark?: boolean): void;
@@ -561,6 +562,9 @@ namespace ts {
                 write(s: string): void {
                     process.stdout.write(s);
                 },
+                writeOutputIsTTY() {
+                    return process.stdout.isTTY;
+                },
                 readFile,
                 writeFile,
                 watchFile: getWatchFile(),
diff --git a/src/compiler/tsc.ts b/src/compiler/tsc.ts
index f16ca98c93dac..3c73eba86ef1a 100644
--- a/src/compiler/tsc.ts
+++ b/src/compiler/tsc.ts
@@ -19,11 +19,18 @@ namespace ts {
 
     let reportDiagnostic = createDiagnosticReporter(sys);
     function updateReportDiagnostic(options: CompilerOptions) {
-        if (options.pretty) {
+        if (shouldBePretty(options)) {
             reportDiagnostic = createDiagnosticReporter(sys, /*pretty*/ true);
         }
     }
 
+    function shouldBePretty(options: CompilerOptions) {
+        if (typeof options.pretty === "undefined") {
+            return !!sys.writeOutputIsTTY && sys.writeOutputIsTTY();
+        }
+        return options.pretty;
+    }
+
     function padLeft(s: string, length: number) {
         while (s.length < length) {
             s = " " + s;
@@ -159,7 +166,7 @@ namespace ts {
     }
 
     function createWatchStatusReporter(options: CompilerOptions) {
-        return ts.createWatchStatusReporter(sys, !!options.pretty);
+        return ts.createWatchStatusReporter(sys, shouldBePretty(options));
     }
 
     function createWatchOfConfigFile(configParseResult: ParsedCommandLine, optionsToExtend: CompilerOptions) {
diff --git a/src/compiler/types.ts b/src/compiler/types.ts
index 987d403e7cd9e..8962a7d028059 100644
--- a/src/compiler/types.ts
+++ b/src/compiler/types.ts
@@ -4193,7 +4193,7 @@ namespace ts {
         preserveSymlinks?: boolean;
         /* @internal */ preserveWatchOutput?: boolean;
         project?: string;
-        /* @internal */ pretty?: DiagnosticStyle;
+        /* @internal */ pretty?: boolean;
         reactNamespace?: string;
         jsxFactory?: string;
         removeComments?: boolean;
@@ -4291,12 +4291,6 @@ namespace ts {
         JSX,
     }
 
-    /* @internal */
-    export const enum DiagnosticStyle {
-        Simple,
-        Pretty,
-    }
-
     /** Either a parsed command line or a parsed tsconfig.json */
     export interface ParsedCommandLine {
         options: CompilerOptions;
diff --git a/tests/baselines/reference/api/tsserverlibrary.d.ts b/tests/baselines/reference/api/tsserverlibrary.d.ts
index 2e8e3f3871df3..be11525ffb76d 100644
--- a/tests/baselines/reference/api/tsserverlibrary.d.ts
+++ b/tests/baselines/reference/api/tsserverlibrary.d.ts
@@ -2888,6 +2888,7 @@ declare namespace ts {
         newLine: string;
         useCaseSensitiveFileNames: boolean;
         write(s: string): void;
+        writeOutputIsTTY?(): boolean;
         readFile(path: string, encoding?: string): string | undefined;
         getFileSize?(path: string): number;
         writeFile(path: string, data: string, writeByteOrderMark?: boolean): void;
diff --git a/tests/baselines/reference/api/typescript.d.ts b/tests/baselines/reference/api/typescript.d.ts
index 378949d5b5b07..c0cab668854c6 100644
--- a/tests/baselines/reference/api/typescript.d.ts
+++ b/tests/baselines/reference/api/typescript.d.ts
@@ -2888,6 +2888,7 @@ declare namespace ts {
         newLine: string;
         useCaseSensitiveFileNames: boolean;
         write(s: string): void;
+        writeOutputIsTTY?(): boolean;
         readFile(path: string, encoding?: string): string | undefined;
         getFileSize?(path: string): number;
         writeFile(path: string, data: string, writeByteOrderMark?: boolean): void;