diff --git a/lib/tsc.js b/lib/tsc.js
index f5d85ee65da..00d01da568a 100644
--- a/lib/tsc.js
+++ b/lib/tsc.js
@@ -63104,8 +63104,9 @@ var ts;
             if (isInDirectoryPath(rootPath, failedLookupLocationPath)) {
                 return { dir: rootDir, dirPath: rootPath };
             }
-            var dir = ts.getDirectoryPath(ts.getNormalizedAbsolutePath(failedLookupLocation, getCurrentDirectory()));
-            var dirPath = ts.getDirectoryPath(failedLookupLocationPath);
+            return getDirectoryToWatchFromFailedLookupLocationDirectory(ts.getDirectoryPath(ts.getNormalizedAbsolutePath(failedLookupLocation, getCurrentDirectory())), ts.getDirectoryPath(failedLookupLocationPath));
+        }
+        function getDirectoryToWatchFromFailedLookupLocationDirectory(dir, dirPath) {
             while (ts.stringContains(dirPath, "/node_modules/")) {
                 dir = ts.getDirectoryPath(dir);
                 dirPath = ts.getDirectoryPath(dirPath);
@@ -63307,13 +63308,27 @@ var ts;
         function closeTypeRootsWatch() {
             ts.clearMap(typeRootsWatches, ts.closeFileWatcher);
         }
-        function createTypeRootsWatch(_typeRootPath, typeRoot) {
+        function getDirectoryToWatchFailedLookupLocationFromTypeRoot(typeRoot, typeRootPath) {
+            if (allFilesHaveInvalidatedResolution) {
+                return undefined;
+            }
+            if (isInDirectoryPath(rootPath, typeRootPath)) {
+                return rootPath;
+            }
+            var _a = getDirectoryToWatchFromFailedLookupLocationDirectory(typeRoot, typeRootPath), dirPath = _a.dirPath, ignore = _a.ignore;
+            return !ignore && directoryWatchesOfFailedLookups.has(dirPath) && dirPath;
+        }
+        function createTypeRootsWatch(typeRootPath, typeRoot) {
             return resolutionHost.watchTypeRootsDirectory(typeRoot, function (fileOrDirectory) {
                 var fileOrDirectoryPath = resolutionHost.toPath(fileOrDirectory);
                 if (cachedDirectoryStructureHost) {
                     cachedDirectoryStructureHost.addOrDeleteFileOrDirectory(fileOrDirectory, fileOrDirectoryPath);
                 }
                 resolutionHost.onChangedAutomaticTypeDirectiveNames();
+                var dirPath = getDirectoryToWatchFailedLookupLocationFromTypeRoot(typeRoot, typeRootPath);
+                if (dirPath && invalidateResolutionOfFailedLookupLocation(fileOrDirectoryPath, dirPath === fileOrDirectoryPath)) {
+                    resolutionHost.onInvalidatedResolution();
+                }
             }, 1);
         }
         function updateTypeRootsWatch() {
diff --git a/lib/tsserver.js b/lib/tsserver.js
index ff68e8cc867..845fa815403 100644
--- a/lib/tsserver.js
+++ b/lib/tsserver.js
@@ -79274,6 +79274,7 @@ var ts;
             if (!newClassDeclaration) {
                 return undefined;
             }
+            copyComments(ctorDeclaration, newClassDeclaration, sourceFile);
             changes.insertNodeAfter(sourceFile, precedingNode, newClassDeclaration);
             for (var _i = 0, deletes_1 = deletes; _i < deletes_1.length; _i++) {
                 var deleteCallback = deletes_1[_i];
@@ -87032,8 +87033,9 @@ var ts;
             if (isInDirectoryPath(rootPath, failedLookupLocationPath)) {
                 return { dir: rootDir, dirPath: rootPath };
             }
-            var dir = ts.getDirectoryPath(ts.getNormalizedAbsolutePath(failedLookupLocation, getCurrentDirectory()));
-            var dirPath = ts.getDirectoryPath(failedLookupLocationPath);
+            return getDirectoryToWatchFromFailedLookupLocationDirectory(ts.getDirectoryPath(ts.getNormalizedAbsolutePath(failedLookupLocation, getCurrentDirectory())), ts.getDirectoryPath(failedLookupLocationPath));
+        }
+        function getDirectoryToWatchFromFailedLookupLocationDirectory(dir, dirPath) {
             while (ts.stringContains(dirPath, "/node_modules/")) {
                 dir = ts.getDirectoryPath(dir);
                 dirPath = ts.getDirectoryPath(dirPath);
@@ -87235,13 +87237,27 @@ var ts;
         function closeTypeRootsWatch() {
             ts.clearMap(typeRootsWatches, ts.closeFileWatcher);
         }
-        function createTypeRootsWatch(_typeRootPath, typeRoot) {
+        function getDirectoryToWatchFailedLookupLocationFromTypeRoot(typeRoot, typeRootPath) {
+            if (allFilesHaveInvalidatedResolution) {
+                return undefined;
+            }
+            if (isInDirectoryPath(rootPath, typeRootPath)) {
+                return rootPath;
+            }
+            var _a = getDirectoryToWatchFromFailedLookupLocationDirectory(typeRoot, typeRootPath), dirPath = _a.dirPath, ignore = _a.ignore;
+            return !ignore && directoryWatchesOfFailedLookups.has(dirPath) && dirPath;
+        }
+        function createTypeRootsWatch(typeRootPath, typeRoot) {
             return resolutionHost.watchTypeRootsDirectory(typeRoot, function (fileOrDirectory) {
                 var fileOrDirectoryPath = resolutionHost.toPath(fileOrDirectory);
                 if (cachedDirectoryStructureHost) {
                     cachedDirectoryStructureHost.addOrDeleteFileOrDirectory(fileOrDirectory, fileOrDirectoryPath);
                 }
                 resolutionHost.onChangedAutomaticTypeDirectiveNames();
+                var dirPath = getDirectoryToWatchFailedLookupLocationFromTypeRoot(typeRoot, typeRootPath);
+                if (dirPath && invalidateResolutionOfFailedLookupLocation(fileOrDirectoryPath, dirPath === fileOrDirectoryPath)) {
+                    resolutionHost.onInvalidatedResolution();
+                }
             }, 1);
         }
         function updateTypeRootsWatch() {
diff --git a/lib/tsserverlibrary.js b/lib/tsserverlibrary.js
index e799becc910..858ba9e2805 100644
--- a/lib/tsserverlibrary.js
+++ b/lib/tsserverlibrary.js
@@ -94589,6 +94589,7 @@ var ts;
                 this.changes.push({ kind: ChangeKind.Remove, sourceFile: sourceFile, range: range });
                 return this;
             };
+            /** Warning: This deletes comments too. See `copyComments` in `convertFunctionToEs6Class`. */
             ChangeTracker.prototype.deleteNode = function (sourceFile, node, options) {
                 if (options === void 0) { options = {}; }
                 var startPosition = getAdjustedStartPosition(sourceFile, node, options, Position.FullStart);
@@ -95585,6 +95586,7 @@ var ts;
             if (!newClassDeclaration) {
                 return undefined;
             }
+            copyComments(ctorDeclaration, newClassDeclaration, sourceFile);
             // Because the preceding node could be touched, we need to insert nodes before delete nodes.
             changes.insertNodeAfter(sourceFile, precedingNode, newClassDeclaration);
             for (var _i = 0, deletes_1 = deletes; _i < deletes_1.length; _i++) {
@@ -106407,8 +106409,9 @@ var ts;
             if (isInDirectoryPath(rootPath, failedLookupLocationPath)) {
                 return { dir: rootDir, dirPath: rootPath };
             }
-            var dir = ts.getDirectoryPath(ts.getNormalizedAbsolutePath(failedLookupLocation, getCurrentDirectory()));
-            var dirPath = ts.getDirectoryPath(failedLookupLocationPath);
+            return getDirectoryToWatchFromFailedLookupLocationDirectory(ts.getDirectoryPath(ts.getNormalizedAbsolutePath(failedLookupLocation, getCurrentDirectory())), ts.getDirectoryPath(failedLookupLocationPath));
+        }
+        function getDirectoryToWatchFromFailedLookupLocationDirectory(dir, dirPath) {
             // If directory path contains node module, get the most parent node_modules directory for watching
             while (ts.stringContains(dirPath, "/node_modules/")) {
                 dir = ts.getDirectoryPath(dir);
@@ -106635,7 +106638,17 @@ var ts;
         function closeTypeRootsWatch() {
             ts.clearMap(typeRootsWatches, ts.closeFileWatcher);
         }
-        function createTypeRootsWatch(_typeRootPath, typeRoot) {
+        function getDirectoryToWatchFailedLookupLocationFromTypeRoot(typeRoot, typeRootPath) {
+            if (allFilesHaveInvalidatedResolution) {
+                return undefined;
+            }
+            if (isInDirectoryPath(rootPath, typeRootPath)) {
+                return rootPath;
+            }
+            var _a = getDirectoryToWatchFromFailedLookupLocationDirectory(typeRoot, typeRootPath), dirPath = _a.dirPath, ignore = _a.ignore;
+            return !ignore && directoryWatchesOfFailedLookups.has(dirPath) && dirPath;
+        }
+        function createTypeRootsWatch(typeRootPath, typeRoot) {
             // Create new watch and recursive info
             return resolutionHost.watchTypeRootsDirectory(typeRoot, function (fileOrDirectory) {
                 var fileOrDirectoryPath = resolutionHost.toPath(fileOrDirectory);
@@ -106647,6 +106660,12 @@ var ts;
                 // We could potentially store more data here about whether it was/would be really be used or not
                 // and with that determine to trigger compilation but for now this is enough
                 resolutionHost.onChangedAutomaticTypeDirectiveNames();
+                // Since directory watchers invoked are flaky, the failed lookup location events might not be triggered
+                // So handle to failed lookup locations here as well to ensure we are invalidating resolutions
+                var dirPath = getDirectoryToWatchFailedLookupLocationFromTypeRoot(typeRoot, typeRootPath);
+                if (dirPath && invalidateResolutionOfFailedLookupLocation(fileOrDirectoryPath, dirPath === fileOrDirectoryPath)) {
+                    resolutionHost.onInvalidatedResolution();
+                }
             }, 1 /* Recursive */);
         }
         /**
diff --git a/lib/typescript.js b/lib/typescript.js
index 827452e5715..0153fb9c7c9 100644
--- a/lib/typescript.js
+++ b/lib/typescript.js
@@ -78594,8 +78594,9 @@ var ts;
             if (isInDirectoryPath(rootPath, failedLookupLocationPath)) {
                 return { dir: rootDir, dirPath: rootPath };
             }
-            var dir = ts.getDirectoryPath(ts.getNormalizedAbsolutePath(failedLookupLocation, getCurrentDirectory()));
-            var dirPath = ts.getDirectoryPath(failedLookupLocationPath);
+            return getDirectoryToWatchFromFailedLookupLocationDirectory(ts.getDirectoryPath(ts.getNormalizedAbsolutePath(failedLookupLocation, getCurrentDirectory())), ts.getDirectoryPath(failedLookupLocationPath));
+        }
+        function getDirectoryToWatchFromFailedLookupLocationDirectory(dir, dirPath) {
             // If directory path contains node module, get the most parent node_modules directory for watching
             while (ts.stringContains(dirPath, "/node_modules/")) {
                 dir = ts.getDirectoryPath(dir);
@@ -78822,7 +78823,17 @@ var ts;
         function closeTypeRootsWatch() {
             ts.clearMap(typeRootsWatches, ts.closeFileWatcher);
         }
-        function createTypeRootsWatch(_typeRootPath, typeRoot) {
+        function getDirectoryToWatchFailedLookupLocationFromTypeRoot(typeRoot, typeRootPath) {
+            if (allFilesHaveInvalidatedResolution) {
+                return undefined;
+            }
+            if (isInDirectoryPath(rootPath, typeRootPath)) {
+                return rootPath;
+            }
+            var _a = getDirectoryToWatchFromFailedLookupLocationDirectory(typeRoot, typeRootPath), dirPath = _a.dirPath, ignore = _a.ignore;
+            return !ignore && directoryWatchesOfFailedLookups.has(dirPath) && dirPath;
+        }
+        function createTypeRootsWatch(typeRootPath, typeRoot) {
             // Create new watch and recursive info
             return resolutionHost.watchTypeRootsDirectory(typeRoot, function (fileOrDirectory) {
                 var fileOrDirectoryPath = resolutionHost.toPath(fileOrDirectory);
@@ -78834,6 +78845,12 @@ var ts;
                 // We could potentially store more data here about whether it was/would be really be used or not
                 // and with that determine to trigger compilation but for now this is enough
                 resolutionHost.onChangedAutomaticTypeDirectiveNames();
+                // Since directory watchers invoked are flaky, the failed lookup location events might not be triggered
+                // So handle to failed lookup locations here as well to ensure we are invalidating resolutions
+                var dirPath = getDirectoryToWatchFailedLookupLocationFromTypeRoot(typeRoot, typeRootPath);
+                if (dirPath && invalidateResolutionOfFailedLookupLocation(fileOrDirectoryPath, dirPath === fileOrDirectoryPath)) {
+                    resolutionHost.onInvalidatedResolution();
+                }
             }, 1 /* Recursive */);
         }
         /**
@@ -96151,6 +96168,7 @@ var ts;
                 this.changes.push({ kind: ChangeKind.Remove, sourceFile: sourceFile, range: range });
                 return this;
             };
+            /** Warning: This deletes comments too. See `copyComments` in `convertFunctionToEs6Class`. */
             ChangeTracker.prototype.deleteNode = function (sourceFile, node, options) {
                 if (options === void 0) { options = {}; }
                 var startPosition = getAdjustedStartPosition(sourceFile, node, options, Position.FullStart);
@@ -97147,6 +97165,7 @@ var ts;
             if (!newClassDeclaration) {
                 return undefined;
             }
+            copyComments(ctorDeclaration, newClassDeclaration, sourceFile);
             // Because the preceding node could be touched, we need to insert nodes before delete nodes.
             changes.insertNodeAfter(sourceFile, precedingNode, newClassDeclaration);
             for (var _i = 0, deletes_1 = deletes; _i < deletes_1.length; _i++) {
diff --git a/lib/typescriptServices.js b/lib/typescriptServices.js
index 827452e5715..0153fb9c7c9 100644
--- a/lib/typescriptServices.js
+++ b/lib/typescriptServices.js
@@ -78594,8 +78594,9 @@ var ts;
             if (isInDirectoryPath(rootPath, failedLookupLocationPath)) {
                 return { dir: rootDir, dirPath: rootPath };
             }
-            var dir = ts.getDirectoryPath(ts.getNormalizedAbsolutePath(failedLookupLocation, getCurrentDirectory()));
-            var dirPath = ts.getDirectoryPath(failedLookupLocationPath);
+            return getDirectoryToWatchFromFailedLookupLocationDirectory(ts.getDirectoryPath(ts.getNormalizedAbsolutePath(failedLookupLocation, getCurrentDirectory())), ts.getDirectoryPath(failedLookupLocationPath));
+        }
+        function getDirectoryToWatchFromFailedLookupLocationDirectory(dir, dirPath) {
             // If directory path contains node module, get the most parent node_modules directory for watching
             while (ts.stringContains(dirPath, "/node_modules/")) {
                 dir = ts.getDirectoryPath(dir);
@@ -78822,7 +78823,17 @@ var ts;
         function closeTypeRootsWatch() {
             ts.clearMap(typeRootsWatches, ts.closeFileWatcher);
         }
-        function createTypeRootsWatch(_typeRootPath, typeRoot) {
+        function getDirectoryToWatchFailedLookupLocationFromTypeRoot(typeRoot, typeRootPath) {
+            if (allFilesHaveInvalidatedResolution) {
+                return undefined;
+            }
+            if (isInDirectoryPath(rootPath, typeRootPath)) {
+                return rootPath;
+            }
+            var _a = getDirectoryToWatchFromFailedLookupLocationDirectory(typeRoot, typeRootPath), dirPath = _a.dirPath, ignore = _a.ignore;
+            return !ignore && directoryWatchesOfFailedLookups.has(dirPath) && dirPath;
+        }
+        function createTypeRootsWatch(typeRootPath, typeRoot) {
             // Create new watch and recursive info
             return resolutionHost.watchTypeRootsDirectory(typeRoot, function (fileOrDirectory) {
                 var fileOrDirectoryPath = resolutionHost.toPath(fileOrDirectory);
@@ -78834,6 +78845,12 @@ var ts;
                 // We could potentially store more data here about whether it was/would be really be used or not
                 // and with that determine to trigger compilation but for now this is enough
                 resolutionHost.onChangedAutomaticTypeDirectiveNames();
+                // Since directory watchers invoked are flaky, the failed lookup location events might not be triggered
+                // So handle to failed lookup locations here as well to ensure we are invalidating resolutions
+                var dirPath = getDirectoryToWatchFailedLookupLocationFromTypeRoot(typeRoot, typeRootPath);
+                if (dirPath && invalidateResolutionOfFailedLookupLocation(fileOrDirectoryPath, dirPath === fileOrDirectoryPath)) {
+                    resolutionHost.onInvalidatedResolution();
+                }
             }, 1 /* Recursive */);
         }
         /**
@@ -96151,6 +96168,7 @@ var ts;
                 this.changes.push({ kind: ChangeKind.Remove, sourceFile: sourceFile, range: range });
                 return this;
             };
+            /** Warning: This deletes comments too. See `copyComments` in `convertFunctionToEs6Class`. */
             ChangeTracker.prototype.deleteNode = function (sourceFile, node, options) {
                 if (options === void 0) { options = {}; }
                 var startPosition = getAdjustedStartPosition(sourceFile, node, options, Position.FullStart);
@@ -97147,6 +97165,7 @@ var ts;
             if (!newClassDeclaration) {
                 return undefined;
             }
+            copyComments(ctorDeclaration, newClassDeclaration, sourceFile);
             // Because the preceding node could be touched, we need to insert nodes before delete nodes.
             changes.insertNodeAfter(sourceFile, precedingNode, newClassDeclaration);
             for (var _i = 0, deletes_1 = deletes; _i < deletes_1.length; _i++) {