diff --git a/python/src/com/jetbrains/python/codeInsight/intentions/PyAnnotateVariableTypeIntention.java b/python/src/com/jetbrains/python/codeInsight/intentions/PyAnnotateVariableTypeIntention.java
index 288ed125efec..53d503174ff2 100644
--- a/python/src/com/jetbrains/python/codeInsight/intentions/PyAnnotateVariableTypeIntention.java
+++ b/python/src/com/jetbrains/python/codeInsight/intentions/PyAnnotateVariableTypeIntention.java
@@ -95,7 +95,10 @@ public class PyAnnotateVariableTypeIntention extends PyBaseIntentionAction {
     PyTypeHintGenerationUtil.insertVariableAnnotation(target, annotationText);
   }
 
-  private void insertVariableTypeComment(@NotNull PyTargetExpression target) {
-
+  private static void insertVariableTypeComment(@NotNull PyTargetExpression target) {
+    final TypeEvalContext context = TypeEvalContext.userInitiated(target.getProject(), target.getContainingFile());
+    final PyType inferredType = context.getType(target);
+    final String annotationText = PythonDocumentationProvider.getTypeName(inferredType, context);
+    PyTypeHintGenerationUtil.insertVariableTypeComment(target, annotationText);
   }
 }
diff --git a/python/src/com/jetbrains/python/codeInsight/intentions/PyTypeHintGenerationUtil.java b/python/src/com/jetbrains/python/codeInsight/intentions/PyTypeHintGenerationUtil.java
index 9c0278101c6a..73ddc520c011 100644
--- a/python/src/com/jetbrains/python/codeInsight/intentions/PyTypeHintGenerationUtil.java
+++ b/python/src/com/jetbrains/python/codeInsight/intentions/PyTypeHintGenerationUtil.java
@@ -38,4 +38,23 @@ public class PyTypeHintGenerationUtil {
     final PyAssignmentStatement assignment = as(target.getParent(), PyAssignmentStatement.class);
     return assignment != null && assignment.getRawTargets().length == 1 && assignment.getLeftHandSideExpression() == target;
   }
+
+  public static void insertVariableTypeComment(@NotNull PyTargetExpression target, @NotNull String annotation) {
+    final PyStatement statement = PsiTreeUtil.getParentOfType(target, PyStatement.class);
+    final String typeCommentText = "  # type: " + annotation;
+    if (statement instanceof PyAssignmentStatement) {
+      PyUtil.updateDocumentUnblockedAndCommitted(target, document -> {
+        document.insertString(statement.getTextRange().getEndOffset(), typeCommentText);
+      });
+    }
+    else if (statement instanceof PyWithStatement || statement instanceof PyForStatement) {
+      PyUtil.updateDocumentUnblockedAndCommitted(target, document -> {
+        final PyStatementListContainer container = statement instanceof PyForStatement ?
+                                                   ((PyForStatement)statement).getForPart() :
+                                                   (PyWithStatement)statement;
+        final int endOffset = PyUtil.getHeaderEndAnchor(container).getTextRange().getEndOffset();
+        document.insertString(endOffset, typeCommentText);
+      });
+    }
+  }
 }
diff --git a/python/src/com/jetbrains/python/psi/PyUtil.java b/python/src/com/jetbrains/python/psi/PyUtil.java
index e0ccc25c53e0..a15dd29953ce 100644
--- a/python/src/com/jetbrains/python/psi/PyUtil.java
+++ b/python/src/com/jetbrains/python/psi/PyUtil.java
@@ -865,8 +865,13 @@ public class PyUtil {
    */
   @Nullable
   public static PsiComment getCommentOnHeaderLine(@NotNull PyStatementListContainer container) {
+    return as(getHeaderEndAnchor(container), PsiComment.class);
+  }
+
+  @NotNull
+  public static PsiElement getHeaderEndAnchor(@NotNull PyStatementListContainer container) {
     final PyStatementList statementList = container.getStatementList();
-    return as(PyPsiUtils.getPrevNonWhitespaceSibling(statementList), PsiComment.class);
+    return ObjectUtils.notNull(PyPsiUtils.getPrevNonWhitespaceSibling(statementList));
   }
 
   public static boolean isPy2ReservedWord(@NotNull PyReferenceExpression node) {
diff --git a/python/testData/intentions/PyAnnotateVariableTypeIntentionTest/typeCommentLocalChainedAssignmentTarget.py b/python/testData/intentions/PyAnnotateVariableTypeIntentionTest/typeCommentLocalChainedAssignmentTarget.py
new file mode 100644
index 000000000000..e1b3a1ccf2fd
--- /dev/null
+++ b/python/testData/intentions/PyAnnotateVariableTypeIntentionTest/typeCommentLocalChainedAssignmentTarget.py
@@ -0,0 +1,3 @@
+def func():
+    var = another = 'spam'
+    v<caret>ar
\ No newline at end of file
diff --git a/python/testData/intentions/PyAnnotateVariableTypeIntentionTest/typeCommentLocalChainedAssignmentTarget_after.py b/python/testData/intentions/PyAnnotateVariableTypeIntentionTest/typeCommentLocalChainedAssignmentTarget_after.py
new file mode 100644
index 000000000000..831ed3665c3a
--- /dev/null
+++ b/python/testData/intentions/PyAnnotateVariableTypeIntentionTest/typeCommentLocalChainedAssignmentTarget_after.py
@@ -0,0 +1,3 @@
+def func():
+    var = another = 'spam'  # type: str
+    var
\ No newline at end of file
diff --git a/python/testData/intentions/PyAnnotateVariableTypeIntentionTest/typeCommentLocalForTarget.py b/python/testData/intentions/PyAnnotateVariableTypeIntentionTest/typeCommentLocalForTarget.py
new file mode 100644
index 000000000000..538221a6b634
--- /dev/null
+++ b/python/testData/intentions/PyAnnotateVariableTypeIntentionTest/typeCommentLocalForTarget.py
@@ -0,0 +1,3 @@
+def func():
+    for var in 'spam':
+        v<caret>ar
diff --git a/python/testData/intentions/PyAnnotateVariableTypeIntentionTest/typeCommentLocalForTarget_after.py b/python/testData/intentions/PyAnnotateVariableTypeIntentionTest/typeCommentLocalForTarget_after.py
new file mode 100644
index 000000000000..93d47f20b721
--- /dev/null
+++ b/python/testData/intentions/PyAnnotateVariableTypeIntentionTest/typeCommentLocalForTarget_after.py
@@ -0,0 +1,3 @@
+def func():
+    for var in 'spam':  # type: str
+        var
diff --git a/python/testData/intentions/PyAnnotateVariableTypeIntentionTest/typeCommentLocalSimpleAssignmentTarget.py b/python/testData/intentions/PyAnnotateVariableTypeIntentionTest/typeCommentLocalSimpleAssignmentTarget.py
new file mode 100644
index 000000000000..bfdb8566d32c
--- /dev/null
+++ b/python/testData/intentions/PyAnnotateVariableTypeIntentionTest/typeCommentLocalSimpleAssignmentTarget.py
@@ -0,0 +1,3 @@
+def func():
+    var = 'spam'
+    v<caret>ar
diff --git a/python/testData/intentions/PyAnnotateVariableTypeIntentionTest/typeCommentLocalSimpleAssignmentTargetInParentheses.py b/python/testData/intentions/PyAnnotateVariableTypeIntentionTest/typeCommentLocalSimpleAssignmentTargetInParentheses.py
new file mode 100644
index 000000000000..820891b8cb69
--- /dev/null
+++ b/python/testData/intentions/PyAnnotateVariableTypeIntentionTest/typeCommentLocalSimpleAssignmentTargetInParentheses.py
@@ -0,0 +1,3 @@
+def func():
+    (var) = 'spam'
+    v<caret>ar
diff --git a/python/testData/intentions/PyAnnotateVariableTypeIntentionTest/typeCommentLocalSimpleAssignmentTargetInParentheses_after.py b/python/testData/intentions/PyAnnotateVariableTypeIntentionTest/typeCommentLocalSimpleAssignmentTargetInParentheses_after.py
new file mode 100644
index 000000000000..07928c0317bb
--- /dev/null
+++ b/python/testData/intentions/PyAnnotateVariableTypeIntentionTest/typeCommentLocalSimpleAssignmentTargetInParentheses_after.py
@@ -0,0 +1,3 @@
+def func():
+    (var) = 'spam'  # type: Any
+    var
diff --git a/python/testData/intentions/PyAnnotateVariableTypeIntentionTest/typeCommentLocalSimpleAssignmentTarget_after.py b/python/testData/intentions/PyAnnotateVariableTypeIntentionTest/typeCommentLocalSimpleAssignmentTarget_after.py
new file mode 100644
index 000000000000..765e9d1db6ea
--- /dev/null
+++ b/python/testData/intentions/PyAnnotateVariableTypeIntentionTest/typeCommentLocalSimpleAssignmentTarget_after.py
@@ -0,0 +1,3 @@
+def func():
+    var = 'spam'  # type: str
+    var
diff --git a/python/testData/intentions/PyAnnotateVariableTypeIntentionTest/typeCommentLocalUnpackedAssignmentTarget.py b/python/testData/intentions/PyAnnotateVariableTypeIntentionTest/typeCommentLocalUnpackedAssignmentTarget.py
new file mode 100644
index 000000000000..05cb637ffc2c
--- /dev/null
+++ b/python/testData/intentions/PyAnnotateVariableTypeIntentionTest/typeCommentLocalUnpackedAssignmentTarget.py
@@ -0,0 +1,3 @@
+def func():
+    var, _ = 'spam', 42
+    v<caret>ar
diff --git a/python/testData/intentions/PyAnnotateVariableTypeIntentionTest/typeCommentLocalUnpackedAssignmentTarget_after.py b/python/testData/intentions/PyAnnotateVariableTypeIntentionTest/typeCommentLocalUnpackedAssignmentTarget_after.py
new file mode 100644
index 000000000000..2c573ff21f6a
--- /dev/null
+++ b/python/testData/intentions/PyAnnotateVariableTypeIntentionTest/typeCommentLocalUnpackedAssignmentTarget_after.py
@@ -0,0 +1,3 @@
+def func():
+    var, _ = 'spam', 42  # type: (str, int)
+    var
diff --git a/python/testData/intentions/PyAnnotateVariableTypeIntentionTest/typeCommentLocalWithTarget.py b/python/testData/intentions/PyAnnotateVariableTypeIntentionTest/typeCommentLocalWithTarget.py
new file mode 100644
index 000000000000..06db7a3f427f
--- /dev/null
+++ b/python/testData/intentions/PyAnnotateVariableTypeIntentionTest/typeCommentLocalWithTarget.py
@@ -0,0 +1,3 @@
+def func():
+    with open('file.txt') as var:
+        v<caret>ar
diff --git a/python/testData/intentions/PyAnnotateVariableTypeIntentionTest/typeCommentLocalWithTarget_after.py b/python/testData/intentions/PyAnnotateVariableTypeIntentionTest/typeCommentLocalWithTarget_after.py
new file mode 100644
index 000000000000..fdd8ca797bbc
--- /dev/null
+++ b/python/testData/intentions/PyAnnotateVariableTypeIntentionTest/typeCommentLocalWithTarget_after.py
@@ -0,0 +1,3 @@
+def func():
+    with open('file.txt') as var:  # type: BinaryIO
+        var
diff --git a/python/testSrc/com/jetbrains/python/intentions/PyAnnotateVariableTypeIntentionTest.java b/python/testSrc/com/jetbrains/python/intentions/PyAnnotateVariableTypeIntentionTest.java
index ff6c59ee88c2..e3bbbfeaac3d 100644
--- a/python/testSrc/com/jetbrains/python/intentions/PyAnnotateVariableTypeIntentionTest.java
+++ b/python/testSrc/com/jetbrains/python/intentions/PyAnnotateVariableTypeIntentionTest.java
@@ -33,6 +33,30 @@ public class PyAnnotateVariableTypeIntentionTest extends PyIntentionTestCase {
     doTestAnnotation();
   }
 
+  public void testTypeCommentLocalSimpleAssignmentTarget() {
+    doTestTypeComment();
+  }
+
+  public void testTypeCommentLocalSimpleAssignmentTargetInParentheses() {
+    doTestTypeComment();
+  }
+
+  public void testTypeCommentLocalUnpackedAssignmentTarget() {
+    doTestTypeComment();
+  }
+
+  public void testTypeCommentLocalChainedAssignmentTarget() {
+    doTestTypeComment();
+  }
+
+  public void testTypeCommentLocalForTarget() {
+    doTestTypeComment();
+  }
+
+  public void testTypeCommentLocalWithTarget() {
+    doTestTypeComment();
+  }
+
   private void doTestAnnotation() {
     doTest(LanguageLevel.PYTHON36);
   }