diff --git a/src/compiler/program.ts b/src/compiler/program.ts
index 0c8444daa2fc9..59b57bfa99a41 100644
--- a/src/compiler/program.ts
+++ b/src/compiler/program.ts
@@ -96,35 +96,51 @@ namespace ts {
             if (existingDirectories.has(directoryPath)) {
                 return true;
             }
-            if (system.directoryExists(directoryPath)) {
+            if ((compilerHost.directoryExists || system.directoryExists)(directoryPath)) {
                 existingDirectories.set(directoryPath, true);
                 return true;
             }
             return false;
         }
 
-        function ensureDirectoriesExist(directoryPath: string) {
-            if (directoryPath.length > getRootLength(directoryPath) && !directoryExists(directoryPath)) {
-                const parentDirectory = getDirectoryPath(directoryPath);
-                ensureDirectoriesExist(parentDirectory);
-                if (compilerHost.createDirectory) {
-                    compilerHost.createDirectory(directoryPath);
-                }
-                else {
-                    system.createDirectory(directoryPath);
+        function writeFile(fileName: string, data: string, writeByteOrderMark: boolean, onError?: (message: string) => void) {
+            try {
+                performance.mark("beforeIOWrite");
+
+                // NOTE: If patchWriteFileEnsuringDirectory has been called,
+                // the system.writeFile will do its own directory creation and
+                // the ensureDirectoriesExist call will always be redundant.
+                writeFileEnsuringDirectories(
+                    fileName,
+                    data,
+                    writeByteOrderMark,
+                    (path, data, writeByteOrderMark) => writeFileWorker(path, data, writeByteOrderMark),
+                    path => (compilerHost.createDirectory || system.createDirectory)(path),
+                    path => directoryExists(path));
+
+                performance.mark("afterIOWrite");
+                performance.measure("I/O Write", "beforeIOWrite", "afterIOWrite");
+            }
+            catch (e) {
+                if (onError) {
+                    onError(e.message);
                 }
             }
         }
 
         let outputFingerprints: Map<OutputFingerprint>;
+        function writeFileWorker(fileName: string, data: string, writeByteOrderMark: boolean) {
+            if (!isWatchSet(options) || !system.createHash || !system.getModifiedTime) {
+                system.writeFile(fileName, data, writeByteOrderMark);
+                return;
+            }
 
-        function writeFileIfUpdated(fileName: string, data: string, writeByteOrderMark: boolean): void {
             if (!outputFingerprints) {
                 outputFingerprints = createMap<OutputFingerprint>();
             }
 
-            const hash = system.createHash!(data); // TODO: GH#18217
-            const mtimeBefore = system.getModifiedTime!(fileName); // TODO: GH#18217
+            const hash = system.createHash(data);
+            const mtimeBefore = system.getModifiedTime(fileName);
 
             if (mtimeBefore) {
                 const fingerprint = outputFingerprints.get(fileName);
@@ -139,7 +155,7 @@ namespace ts {
 
             system.writeFile(fileName, data, writeByteOrderMark);
 
-            const mtimeAfter = system.getModifiedTime!(fileName) || missingFileModifiedTime; // TODO: GH#18217
+            const mtimeAfter = system.getModifiedTime(fileName) || missingFileModifiedTime;
 
             outputFingerprints.set(fileName, {
                 hash,
@@ -148,28 +164,6 @@ namespace ts {
             });
         }
 
-        function writeFile(fileName: string, data: string, writeByteOrderMark: boolean, onError?: (message: string) => void) {
-            try {
-                performance.mark("beforeIOWrite");
-                ensureDirectoriesExist(getDirectoryPath(normalizePath(fileName)));
-
-                if (isWatchSet(options) && system.createHash && system.getModifiedTime) {
-                    writeFileIfUpdated(fileName, data, writeByteOrderMark);
-                }
-                else {
-                    system.writeFile(fileName, data, writeByteOrderMark);
-                }
-
-                performance.mark("afterIOWrite");
-                performance.measure("I/O Write", "beforeIOWrite", "afterIOWrite");
-            }
-            catch (e) {
-                if (onError) {
-                    onError(e.message);
-                }
-            }
-        }
-
         function getDefaultLibLocation(): string {
             return getDirectoryPath(normalizePath(system.getExecutingFilePath()));
         }
diff --git a/src/compiler/sys.ts b/src/compiler/sys.ts
index ad866cba13065..31b422a12b9ef 100644
--- a/src/compiler/sys.ts
+++ b/src/compiler/sys.ts
@@ -522,17 +522,6 @@ namespace ts {
         }
     }
 
-    function recursiveCreateDirectory(directoryPath: string, sys: System) {
-        const basePath = getDirectoryPath(directoryPath);
-        const shouldCreateParent = basePath !== "" && directoryPath !== basePath && !sys.directoryExists(basePath);
-        if (shouldCreateParent) {
-            recursiveCreateDirectory(basePath, sys);
-        }
-        if (shouldCreateParent || !sys.directoryExists(directoryPath)) {
-            sys.createDirectory(directoryPath);
-        }
-    }
-
     /**
      * patch writefile to create folder before writing the file
      */
@@ -540,13 +529,14 @@ namespace ts {
     export function patchWriteFileEnsuringDirectory(sys: System) {
         // patch writefile to create folder before writing the file
         const originalWriteFile = sys.writeFile;
-        sys.writeFile = (path, data, writeBom) => {
-            const directoryPath = getDirectoryPath(normalizeSlashes(path));
-            if (directoryPath && !sys.directoryExists(directoryPath)) {
-                recursiveCreateDirectory(directoryPath, sys);
-            }
-            originalWriteFile.call(sys, path, data, writeBom);
-        };
+        sys.writeFile = (path, data, writeBom) =>
+            writeFileEnsuringDirectories(
+                path,
+                data,
+                !!writeBom,
+                (path, data, writeByteOrderMark) => originalWriteFile.call(sys, path, data, writeByteOrderMark),
+                path => sys.createDirectory(path),
+                path => sys.directoryExists(path));
     }
 
     /*@internal*/
diff --git a/src/compiler/utilities.ts b/src/compiler/utilities.ts
index 2fb1173deef3a..ac29da9389989 100644
--- a/src/compiler/utilities.ts
+++ b/src/compiler/utilities.ts
@@ -3700,6 +3700,36 @@ namespace ts {
         }, sourceFiles);
     }
 
+    function ensureDirectoriesExist(
+        directoryPath: string,
+        createDirectory: (path: string) => void,
+        directoryExists: (path: string) => boolean): void {
+        if (directoryPath.length > getRootLength(directoryPath) && !directoryExists(directoryPath)) {
+            const parentDirectory = getDirectoryPath(directoryPath);
+            ensureDirectoriesExist(parentDirectory, createDirectory, directoryExists);
+            createDirectory(directoryPath);
+        }
+    }
+
+    export function writeFileEnsuringDirectories(
+        path: string,
+        data: string,
+        writeByteOrderMark: boolean,
+        writeFile: (path: string, data: string, writeByteOrderMark: boolean) => void,
+        createDirectory: (path: string) => void,
+        directoryExists: (path: string) => boolean): void {
+
+        // PERF: Checking for directory existence is expensive.  Instead, assume the directory exists
+        // and fall back to creating it if the file write fails.
+        try {
+            writeFile(path, data, writeByteOrderMark);
+        }
+        catch {
+            ensureDirectoriesExist(getDirectoryPath(normalizePath(path)), createDirectory, directoryExists);
+            writeFile(path, data, writeByteOrderMark);
+        }
+    }
+
     export function getLineOfLocalPosition(currentSourceFile: SourceFile, pos: number) {
         return getLineAndCharacterOfPosition(currentSourceFile, pos).line;
     }
diff --git a/src/compiler/watch.ts b/src/compiler/watch.ts
index 06871fc9cacdb..5e8991dbb61e0 100644
--- a/src/compiler/watch.ts
+++ b/src/compiler/watch.ts
@@ -296,20 +296,20 @@ namespace ts {
             readDirectory: maybeBind(host, host.readDirectory),
         };
 
-        function ensureDirectoriesExist(directoryPath: string) {
-            if (directoryPath.length > getRootLength(directoryPath) && !host.directoryExists!(directoryPath)) {
-                const parentDirectory = getDirectoryPath(directoryPath);
-                ensureDirectoriesExist(parentDirectory);
-                if (host.createDirectory) host.createDirectory(directoryPath);
-            }
-        }
-
         function writeFile(fileName: string, text: string, writeByteOrderMark: boolean, onError: (message: string) => void) {
             try {
                 performance.mark("beforeIOWrite");
-                ensureDirectoriesExist(getDirectoryPath(normalizePath(fileName)));
 
-                host.writeFile!(fileName, text, writeByteOrderMark);
+                // NOTE: If patchWriteFileEnsuringDirectory has been called,
+                // the host.writeFile will do its own directory creation and
+                // the ensureDirectoriesExist call will always be redundant.
+                writeFileEnsuringDirectories(
+                    fileName,
+                    text,
+                    writeByteOrderMark,
+                    (path, data, writeByteOrderMark) => host.writeFile!(path, data, writeByteOrderMark),
+                    path => host.createDirectory!(path),
+                    path => host.directoryExists!(path));
 
                 performance.mark("afterIOWrite");
                 performance.measure("I/O Write", "beforeIOWrite", "afterIOWrite");