diff --git a/src/compiler/watch.ts b/src/compiler/watch.ts
index 9ec362a12c0..6b3adfcf3a4 100644
--- a/src/compiler/watch.ts
+++ b/src/compiler/watch.ts
@@ -531,13 +531,13 @@ namespace ts {
         const watchLogLevel = trace ? compilerOptions.extendedDiagnostics ? WatchLogLevel.Verbose :
             compilerOptions.diagnostis ? WatchLogLevel.TriggerOnly : WatchLogLevel.None : WatchLogLevel.None;
         const writeLog: (s: string) => void = watchLogLevel !== WatchLogLevel.None ? trace : noop;
-        const { watchFile, watchFilePath, watchDirectory: watchDirectoryWorker } = getWatchFactory(watchLogLevel, writeLog);
+        const { watchFile, watchFilePath, watchDirectory } = getWatchFactory<string>(watchLogLevel, writeLog);
 
         const getCanonicalFileName = createGetCanonicalFileName(useCaseSensitiveFileNames);
 
         writeLog(`Current directory: ${currentDirectory} CaseSensitiveFileNames: ${useCaseSensitiveFileNames}`);
         if (configFileName) {
-            watchFile(host, configFileName, scheduleProgramReload, PollingInterval.High);
+            watchFile(host, configFileName, scheduleProgramReload, PollingInterval.High, "Config file");
         }
 
         const compilerHost: CompilerHost & ResolutionCacheHost = {
@@ -563,8 +563,8 @@ namespace ts {
             // Members for ResolutionCacheHost
             toPath,
             getCompilationSettings: () => compilerOptions,
-            watchDirectoryOfFailedLookupLocation: watchDirectory,
-            watchTypeRootsDirectory: watchDirectory,
+            watchDirectoryOfFailedLookupLocation: (dir, cb, flags) => watchDirectory(host, dir, cb, flags, "Failed Lookup Locations"),
+            watchTypeRootsDirectory: (dir, cb, flags) => watchDirectory(host, dir, cb, flags, "Type roots"),
             getCachedDirectoryStructureHost: () => cachedDirectoryStructureHost,
             onInvalidatedResolution: scheduleProgramUpdate,
             onChangedAutomaticTypeDirectiveNames: () => {
@@ -728,7 +728,7 @@ namespace ts {
                         (hostSourceFile as FilePresentOnHost).sourceFile = sourceFile;
                         sourceFile.version = hostSourceFile.version.toString();
                         if (!(hostSourceFile as FilePresentOnHost).fileWatcher) {
-                            (hostSourceFile as FilePresentOnHost).fileWatcher = watchFilePath(host, fileName, onSourceFileChange, PollingInterval.Low, path);
+                            (hostSourceFile as FilePresentOnHost).fileWatcher = watchFilePath(host, fileName, onSourceFileChange, PollingInterval.Low, path, "Source file");
                         }
                     }
                     else {
@@ -742,7 +742,7 @@ namespace ts {
                 else {
                     if (sourceFile) {
                         sourceFile.version = initialVersion.toString();
-                        const fileWatcher = watchFilePath(host, fileName, onSourceFileChange, PollingInterval.Low, path);
+                        const fileWatcher = watchFilePath(host, fileName, onSourceFileChange, PollingInterval.Low, path, "Source file");
                         sourceFilesCache.set(path, { sourceFile, version: initialVersion, fileWatcher });
                     }
                     else {
@@ -827,6 +827,7 @@ namespace ts {
             if (timerToUpdateProgram) {
                 host.clearTimeout(timerToUpdateProgram);
             }
+            writeLog("Scheduling update");
             timerToUpdateProgram = host.setTimeout(updateProgram, 250);
         }
 
@@ -852,6 +853,7 @@ namespace ts {
         }
 
         function reloadFileNamesFromConfigFile() {
+            writeLog("Reloading new file names and options");
             const result = getFileNamesFromConfigSpecs(configFileSpecs, getDirectoryPath(configFileName), compilerOptions, parseConfigFileHost);
             if (result.fileNames.length) {
                 configFileParsingDiagnostics = filter(configFileParsingDiagnostics, error => !isErrorNoInputFiles(error));
@@ -913,12 +915,8 @@ namespace ts {
             }
         }
 
-        function watchDirectory(directory: string, cb: DirectoryWatcherCallback, flags: WatchDirectoryFlags) {
-            return watchDirectoryWorker(host, directory, cb, flags);
-        }
-
         function watchMissingFilePath(missingFilePath: Path) {
-            return watchFilePath(host, missingFilePath, onMissingFileChange, PollingInterval.Medium, missingFilePath);
+            return watchFilePath(host, missingFilePath, onMissingFileChange, PollingInterval.Medium, missingFilePath, "Missing file");
         }
 
         function onMissingFileChange(fileName: string, eventKind: FileWatcherEventKind, missingFilePath: Path) {
@@ -951,6 +949,7 @@ namespace ts {
 
         function watchWildcardDirectory(directory: string, flags: WatchDirectoryFlags) {
             return watchDirectory(
+                host,
                 directory,
                 fileOrDirectory => {
                     Debug.assert(!!configFileName);
@@ -978,7 +977,8 @@ namespace ts {
                         scheduleProgramUpdate();
                     }
                 },
-                flags
+                flags,
+                "Wild card directories"
             );
         }
 
diff --git a/src/compiler/watchUtilities.ts b/src/compiler/watchUtilities.ts
index 4fa9b28e162..fca4f858e16 100644
--- a/src/compiler/watchUtilities.ts
+++ b/src/compiler/watchUtilities.ts
@@ -352,11 +352,11 @@ namespace ts {
         watchDirectory: WatchDirectory<X, Y>;
     }
 
-    export function getWatchFactory<X = undefined, Y = undefined>(watchLogLevel: WatchLogLevel, log: (s: string) => void, getDetailWatchInfo?: GetDetailWatchInfo<X, Y>): WatchFactory<X, Y> {
+    export function getWatchFactory<X, Y = undefined>(watchLogLevel: WatchLogLevel, log: (s: string) => void, getDetailWatchInfo?: GetDetailWatchInfo<X, Y>): WatchFactory<X, Y> {
         return getWatchFactoryWith(watchLogLevel, log, getDetailWatchInfo, watchFile, watchDirectory);
     }
 
-    function getWatchFactoryWith<X = undefined, Y = undefined>(watchLogLevel: WatchLogLevel, log: (s: string) => void, getDetailWatchInfo: GetDetailWatchInfo<X, Y> | undefined,
+    function getWatchFactoryWith<X, Y = undefined>(watchLogLevel: WatchLogLevel, log: (s: string) => void, getDetailWatchInfo: GetDetailWatchInfo<X, Y> | undefined,
         watchFile: (host: WatchFileHost, file: string, callback: FileWatcherCallback, watchPriority: PollingInterval) => FileWatcher,
         watchDirectory: (host: WatchDirectoryHost, directory: string, callback: DirectoryWatcherCallback, flags: WatchDirectoryFlags) => FileWatcher): WatchFactory<X, Y> {
         const createFileWatcher: CreateFileWatcher<WatchFileHost, PollingInterval, FileWatcherEventKind, undefined, X, Y> = getCreateFileWatcher(watchLogLevel, watchFile);
@@ -422,8 +422,8 @@ namespace ts {
         }, flags);
     }
 
-    function getWatchInfo<T, X, Y>(file: string, flags: T, detailInfo1: X | undefined, detailInfo2: Y | undefined, getDetailWatchInfo: GetDetailWatchInfo<X, Y> | undefined) {
-        return `WatchInfo: ${file} ${flags} ${getDetailWatchInfo ? getDetailWatchInfo(detailInfo1, detailInfo2) : ""}`;
+    function getWatchInfo<T, X, Y>(file: string, flags: T, detailInfo1: X, detailInfo2: Y | undefined, getDetailWatchInfo: GetDetailWatchInfo<X, Y> | undefined) {
+        return `WatchInfo: ${file} ${flags} ${getDetailWatchInfo ? getDetailWatchInfo(detailInfo1, detailInfo2) : detailInfo1}`;
     }
 
     export function closeFileWatcherOf<T extends { watcher: FileWatcher; }>(objWithWatcher: T) {
diff --git a/src/harness/unittests/tscWatchMode.ts b/src/harness/unittests/tscWatchMode.ts
index ca681a8f8ce..b64b02e301a 100644
--- a/src/harness/unittests/tscWatchMode.ts
+++ b/src/harness/unittests/tscWatchMode.ts
@@ -2257,16 +2257,17 @@ declare module "fs" {
                 "CreatingProgramWith::\n",
                 "  roots: [\"f.ts\"]\n",
                 "  options: {\"extendedDiagnostics\":true}\n",
-                "FileWatcher:: Added:: WatchInfo: f.ts 250 \n",
-                "FileWatcher:: Added:: WatchInfo: /a/lib/lib.d.ts 250 \n"
+                "FileWatcher:: Added:: WatchInfo: f.ts 250 Source file\n",
+                "FileWatcher:: Added:: WatchInfo: /a/lib/lib.d.ts 250 Source file\n"
             ]);
 
             file.content = "//";
             host.reloadFS(files);
             host.runQueuedTimeoutCallbacks();
             checkOutputErrorsIncremental(host, emptyArray, disableConsoleClear, options.extendedDiagnostics && [
-                "FileWatcher:: Triggered with /f.ts1:: WatchInfo: f.ts 250 \n",
-                "Elapsed:: 0ms FileWatcher:: Triggered with /f.ts1:: WatchInfo: f.ts 250 \n"
+                "FileWatcher:: Triggered with /f.ts1:: WatchInfo: f.ts 250 Source file\n",
+                "Scheduling update\n",
+                "Elapsed:: 0ms FileWatcher:: Triggered with /f.ts1:: WatchInfo: f.ts 250 Source file\n"
             ], options.extendedDiagnostics && [
                 "Synchronizing program\n",
                 "CreatingProgramWith::\n",