diff --git a/src/server/editorServices.ts b/src/server/editorServices.ts
index bb3560cbde521..19eb0f552874e 100644
--- a/src/server/editorServices.ts
+++ b/src/server/editorServices.ts
@@ -1816,9 +1816,10 @@ namespace ts.server {
             let info = this.getScriptInfoForPath(path);
             if (!info) {
                 const isDynamic = isDynamicFileName(fileName);
+                const normalizedCurrentDirectory = normalizePath(currentDirectory);
                 Debug.assert(isRootedDiskPath(fileName) || isDynamic || openedByClient, "", () => `${JSON.stringify({ fileName, currentDirectory, hostCurrentDirectory: this.currentDirectory, openKeys: arrayFrom(this.openFilesWithNonRootedDiskPath.keys()) })}\nScript info with non-dynamic relative file name can only be open script info`);
-                Debug.assert(!isRootedDiskPath(fileName) || this.currentDirectory === currentDirectory || !this.openFilesWithNonRootedDiskPath.has(this.toCanonicalFileName(fileName)), "", () => `${JSON.stringify({ fileName, currentDirectory, hostCurrentDirectory: this.currentDirectory, openKeys: arrayFrom(this.openFilesWithNonRootedDiskPath.keys()) })}\nOpen script files with non rooted disk path opened with current directory context cannot have same canonical names`);
-                Debug.assert(!isDynamic || this.currentDirectory === currentDirectory, "", () => `${JSON.stringify({ fileName, currentDirectory, hostCurrentDirectory: this.currentDirectory, openKeys: arrayFrom(this.openFilesWithNonRootedDiskPath.keys()) })}\nDynamic files must always have current directory context since containing external project name will always match the script info name.`);
+                Debug.assert(!isRootedDiskPath(fileName) || this.currentDirectory === normalizedCurrentDirectory || !this.openFilesWithNonRootedDiskPath.has(this.toCanonicalFileName(fileName)), "", () => `${JSON.stringify({ fileName, currentDirectory, hostCurrentDirectory: this.currentDirectory, openKeys: arrayFrom(this.openFilesWithNonRootedDiskPath.keys()) })}\nOpen script files with non rooted disk path opened with current directory context cannot have same canonical names`);
+                Debug.assert(!isDynamic || this.currentDirectory === normalizedCurrentDirectory, "", () => `${JSON.stringify({ fileName, currentDirectory, hostCurrentDirectory: this.currentDirectory, openKeys: arrayFrom(this.openFilesWithNonRootedDiskPath.keys()) })}\nDynamic files must always have current directory context since containing external project name will always match the script info name.`);
                 // If the file is not opened by client and the file doesnot exist on the disk, return
                 if (!openedByClient && !isDynamic && !(hostToQueryFileExistsOn || this.host).fileExists(fileName)) {
                     return;
@@ -1828,7 +1829,7 @@ namespace ts.server {
                 if (!openedByClient) {
                     this.watchClosedScriptInfo(info);
                 }
-                else if (!isRootedDiskPath(fileName) && currentDirectory !== this.currentDirectory) {
+                else if (!isRootedDiskPath(fileName) && normalizedCurrentDirectory !== this.currentDirectory) {
                     // File that is opened by user but isn't rooted disk path
                     this.openFilesWithNonRootedDiskPath.set(this.toCanonicalFileName(fileName), info);
                 }