diff --git a/python/src/com/jetbrains/python/editor/PythonEnterHandler.java b/python/src/com/jetbrains/python/editor/PythonEnterHandler.java
index 266bbdc3dc17..adc0b4a560c5 100644
--- a/python/src/com/jetbrains/python/editor/PythonEnterHandler.java
+++ b/python/src/com/jetbrains/python/editor/PythonEnterHandler.java
@@ -63,7 +63,13 @@ public class PythonEnterHandler implements EnterHandlerDelegate {
     }
 
     PsiElement wrappableBefore = findBeforeCaret(file, offset, IMPLICIT_WRAP_CLASSES);
+    if (isCommentOnOtherLine(doc, offset, wrappableBefore)) {
+      return Result.Continue;
+    }
     PsiElement wrappableAfter = findAfterCaret(file, offset, IMPLICIT_WRAP_CLASSES);
+    if (isCommentOnOtherLine(doc, offset, wrappableAfter)) {
+      return Result.Continue;
+    }
     while (wrappableBefore != null) {
       PsiElement next = PsiTreeUtil.getParentOfType(wrappableBefore, IMPLICIT_WRAP_CLASSES);
       if (next == null) {
@@ -85,6 +91,17 @@ public class PythonEnterHandler implements EnterHandlerDelegate {
     return Result.Continue;
   }
 
+  private static boolean isCommentOnOtherLine(Document doc, int offset, PsiElement other) {
+    if (other instanceof PsiComment) {
+      int otherLine = doc.getLineNumber(other.getTextRange().getStartOffset());
+      int thisLine = doc.getLineNumber(offset);
+      if (otherLine != thisLine) {
+        return true;
+      }
+    }
+    return false;
+  }
+
   @Nullable
   private static PsiElement findStatementBeforeCaret(PsiFile file, int offset) {
     return findBeforeCaret(file, offset, PyStatement.class);
@@ -100,8 +117,8 @@ public class PythonEnterHandler implements EnterHandlerDelegate {
     while(offset > 0) {
       offset--;
       final PsiElement element = file.findElementAt(offset);
-      if (!(element instanceof PsiWhiteSpace)) {
-        return PsiTreeUtil.getParentOfType(element, classes);
+      if (element != null && !(element instanceof PsiWhiteSpace)) {
+        return PsiTreeUtil.getNonStrictParentOfType(element, classes);
       }
     }
     return null;
@@ -111,8 +128,8 @@ public class PythonEnterHandler implements EnterHandlerDelegate {
   private static PsiElement findAfterCaret(PsiFile file, int offset, Class<? extends PsiElement>... classes) {
     while(offset < file.getTextLength()) {
       final PsiElement element = file.findElementAt(offset);
-      if (!(element instanceof PsiWhiteSpace)) {
-        return PsiTreeUtil.getParentOfType(element, classes);
+      if (element != null && !(element instanceof PsiWhiteSpace)) {
+        return PsiTreeUtil.getNonStrictParentOfType(element, classes);
       }
       offset++;
     }
diff --git a/python/testSrc/com/jetbrains/python/PyEditingTest.java b/python/testSrc/com/jetbrains/python/PyEditingTest.java
index 44e64f3ae60e..4e329d899804 100644
--- a/python/testSrc/com/jetbrains/python/PyEditingTest.java
+++ b/python/testSrc/com/jetbrains/python/PyEditingTest.java
@@ -120,6 +120,14 @@ public class PyEditingTest extends PyLightFixtureTestCase {
     doTestEnter("z=1 <caret>2", "z=1 \n2");
   }
 
+  public void testEnterAtStartOfComment() {
+    doTestEnter("# bar\n<caret># foo", "# bar\n\n# foo");
+  }
+
+  public void testEnterAtEndOfComment() {
+    doTestEnter("# bar<caret>\n# foo", "# bar\n\n# foo");
+  }
+
   private void doTestEnter(String before, final String after) {
     int pos = before.indexOf("<caret>");
     before = before.replace("<caret>", "");