diff --git a/python/educational/interactive-learning/src/com/jetbrains/edu/learning/actions/StudyCheckAction.java b/python/educational/interactive-learning/src/com/jetbrains/edu/learning/actions/StudyCheckAction.java
index a47b5a13cbbf..952a58c3b6fc 100644
--- a/python/educational/interactive-learning/src/com/jetbrains/edu/learning/actions/StudyCheckAction.java
+++ b/python/educational/interactive-learning/src/com/jetbrains/edu/learning/actions/StudyCheckAction.java
@@ -35,7 +35,6 @@ import com.intellij.openapi.wm.WindowManager;
 import com.intellij.openapi.wm.ex.StatusBarEx;
 import com.intellij.openapi.wm.ex.WindowManagerEx;
 import com.jetbrains.edu.EduDocumentListener;
-import com.jetbrains.edu.EduNames;
 import com.jetbrains.edu.EduUtils;
 import com.jetbrains.edu.courseFormat.AnswerPlaceholder;
 import com.jetbrains.edu.courseFormat.Task;
@@ -85,26 +84,6 @@ public class StudyCheckAction extends DumbAwareAction {
     }
   }
 
-  private static void deleteWindowDescriptions(@NotNull final Task task, @NotNull final VirtualFile taskDir) {
-    for (Map.Entry<String, TaskFile> entry : task.getTaskFiles().entrySet()) {
-      String name = entry.getKey();
-      VirtualFile virtualFile = taskDir.findChild(name);
-      if (virtualFile == null) {
-        continue;
-      }
-      String windowsFileName = virtualFile.getNameWithoutExtension() + EduNames.WINDOWS_POSTFIX;
-      final VirtualFile windowsFile = taskDir.findChild(windowsFileName);
-      if (windowsFile != null) {
-        ApplicationManager.getApplication().runWriteAction(new Runnable() {
-          @Override
-          public void run() {
-            StudyUtils.deleteFile(windowsFile);
-          }
-        });
-      }
-    }
-  }
-
   private static void drawAllPlaceholders(@NotNull final Project project, @NotNull final Task task, @NotNull final VirtualFile taskDir) {
     for (Map.Entry<String, TaskFile> entry : task.getTaskFiles().entrySet()) {
       String name = entry.getKey();
@@ -219,14 +198,14 @@ public class StudyCheckAction extends DumbAwareAction {
         StudyUtils.updateStudyToolWindow(project);
         drawAllPlaceholders(project, task, taskDir);
         ProjectView.getInstance(project).refresh();
-        deleteWindowDescriptions(task, taskDir);
+        EduUtils.deleteWindowDescriptions(task, taskDir);
         checkInProgress = false;
       }
 
       @Override
       public void onCancel() {
         taskManager.setStatus(task, statusBeforeCheck);
-        deleteWindowDescriptions(task, taskDir);
+        EduUtils.deleteWindowDescriptions(task, taskDir);
         checkInProgress = false;
       }
 
diff --git a/python/educational/src/com/jetbrains/edu/EduUtils.java b/python/educational/src/com/jetbrains/edu/EduUtils.java
index c72b8fb388bb..7808ad2d21f9 100644
--- a/python/educational/src/com/jetbrains/edu/EduUtils.java
+++ b/python/educational/src/com/jetbrains/edu/EduUtils.java
@@ -19,6 +19,7 @@ import com.intellij.openapi.util.TextRange;
 import com.intellij.openapi.vfs.VirtualFile;
 import com.intellij.openapi.vfs.VirtualFileManager;
 import com.jetbrains.edu.courseFormat.AnswerPlaceholder;
+import com.jetbrains.edu.courseFormat.Task;
 import com.jetbrains.edu.courseFormat.TaskFile;
 import org.jetbrains.annotations.NotNull;
 import org.jetbrains.annotations.Nullable;
@@ -106,6 +107,7 @@ public class EduUtils {
     }
     if (taskDir != null) {
       final String name = file.getNameWithoutExtension() + EduNames.WINDOWS_POSTFIX;
+      deleteWindowsFile(taskDir, name);
       PrintWriter printWriter = null;
       try {
         fileWindows = taskDir.createChildData(taskFile, name);
@@ -232,4 +234,33 @@ public class EduUtils {
       }
     }, "Replace Answer Placeholders", "Replace Answer Placeholders");
   }
+
+  public static void deleteWindowDescriptions(@NotNull final Task task, @NotNull final VirtualFile taskDir) {
+    for (Map.Entry<String, TaskFile> entry : task.getTaskFiles().entrySet()) {
+      String name = entry.getKey();
+      VirtualFile virtualFile = taskDir.findChild(name);
+      if (virtualFile == null) {
+        continue;
+      }
+      String windowsFileName = virtualFile.getNameWithoutExtension() + EduNames.WINDOWS_POSTFIX;
+      deleteWindowsFile(taskDir, windowsFileName);
+    }
+  }
+
+  private static void deleteWindowsFile(@NotNull final VirtualFile taskDir, @NotNull final String name) {
+    final VirtualFile fileWindows = taskDir.findChild(name);
+    if (fileWindows != null && fileWindows.exists()) {
+      ApplicationManager.getApplication().runWriteAction(new Runnable() {
+        @Override
+        public void run() {
+          try {
+            fileWindows.delete(taskDir);
+          }
+          catch (IOException e) {
+            LOG.warn("Tried to delete non existed _windows file");
+          }
+        }
+      });
+    }
+  }
 }