diff --git a/Python/Python.sublime-syntax b/Python/Python.sublime-syntax
index ee9400c416..35ee5c01b0 100644
--- a/Python/Python.sublime-syntax
+++ b/Python/Python.sublime-syntax
@@ -411,12 +411,136 @@ contexts:
       pop: true
 
   comments:
+    # Type-ignore can only be used by itself.
+    - match: '(#)\s*(type)(:)\s*(ignore)\b'
+      scope: comment.line.type-hint.python
+      captures:
+        1: punctuation.definition.comment.python
+        2: keyword.other.annotation.type-comment.python
+        3: punctuation.separator.annotation.type-comment.python
+        4: keyword.other.annotation.type-comment.ignore.python
+      push: comments-afterignore
+    - match: '(#)\s*(type)(:)'
+      scope: comment.line.type-hint.python
+      captures:
+        1: punctuation.definition.comment.python
+        2: keyword.other.annotation.type-comment.python
+        3: punctuation.separator.annotation.type-comment.python
+      push: type-comment
     - match: "#"
       scope: punctuation.definition.comment.python
-      push:
-        - meta_scope: comment.line.number-sign.python
+      push: comments-basic-remainder
+
+  comments-basic:
+    - match: "#"
+      scope: punctuation.definition.comment.python
+      set: comments-basic-remainder
+
+  comments-basic-remainder:
+    - meta_scope: comment.line.number-sign.python
+    - match: \n
+      pop: true
+
+  comments-afterignore:
+    - meta_content_scope: comment.line.type-hint.python
+    - match: \n
+      pop: true
+    - match: '(?=#)'
+      set: comments-basic
+    - match: \[
+      # Mypy's # type: ignore[error-code1, error-code2]
+      scope: punctuation.section.brackets.begin.python
+      set:
+        - meta_content_scope: comment.line.type-hint.python
         - match: \n
           pop: true
+        - match: \[
+          scope: invalid.illegal.python
+        - match: '[a-zA-Z_-][a-zA-Z_0-9-]+'
+          scope: constant.other.error-code.python
+        - match: '[0-9]\w*'
+          scope: invalid.illegal.python
+        - match: ','
+          scope: punctuation.separator.sequence.python
+        - match: \]
+          scope: punctuation.section.brackets.end.python
+          set:
+            # Don't allow a second block.
+            - meta_content_scope: comment.line.type-hint.python
+            - match: \n
+              pop: true
+            - match: '(?=#)'
+              set: comments-basic
+            - match: \S
+              scope: invalid.illegal.python
+    - match: \S
+      scope: invalid.illegal.python
+
+  type-comment:
+    - meta_content_scope: comment.line.type-hint.python
+    - match: \n
+      pop: true
+    - match: '(?=#)'
+      set: comments-basic
+    # Don't use expressions here, only a few types are reasonable
+    # as annotations.
+    - include: constants
+    - include: builtin-exceptions
+    - include: builtin-types
+    - include: builtin-functions
+    - match: '{{identifier}}'
+      scope: support.class.python
+    - match: '\s*(\[)'
+      captures:
+        1: meta.item-access.python punctuation.section.brackets.begin.python
+      push:
+        - meta_content_scope: meta.item-access.arguments.python
+        - match: (?=\n)
+          pop: true
+        - match: \]
+          scope: meta.item-access.python punctuation.section.brackets.end.python
+          pop: true
+        - match: ':'
+          scope: punctuation.separator.slice.python
+        - match: '(?=#)'
+        - include: type-comment
+    - match: '\('
+      scope: punctuation.section.parens.begin.python
+      push:
+        - meta_content_scope: meta.function.parameters.python
+        - match: (?=\n)
+          pop: true
+        - match: \)
+          scope: punctuation.section.parens.end.python
+          pop: true
+        - match: \(
+          scope: invalid.illegal.stray.brace.round.python
+        - match: \*{3,}
+          scope: invalid.illegal.syntax.python
+        - match: \*\*
+          scope: keyword.operator.unpacking.mapping.python
+        - match: \*
+          scope: keyword.operator.unpacking.sequence.python
+        - match: '->'
+          scope: invalid.illegal.stray.return.arrow.python
+        - include: type-comment
+    - match: '->'
+      scope: meta.function.return-type.python punctuation.separator.sequence.python
+      set:
+        - meta_content_scope: comment.line.type-hint.python meta.function.return-type.python
+        - match: '->'
+          scope: invalid.illegal.stray.return.arrow.python
+        - include: type-comment
+    - match: ','
+      scope: punctuation.separator.sequence.python
+    - match: \)
+      scope: invalid.illegal.stray.brace.round.python
+    - match: \]
+      scope: invalid.illegal.stray.brace.square.python
+    - match: \}
+      scope: invalid.illegal.stray.brace.curly.python
+    - match: \S
+      scope: invalid.illegal.python
 
   constants:
     - match: \b(None|True|False|Ellipsis|NotImplemented|__debug__)\b
diff --git a/Python/syntax_test_python.py b/Python/syntax_test_python.py
index b33335f30b..ce95391287 100644
--- a/Python/syntax_test_python.py
+++ b/Python/syntax_test_python.py
@@ -1487,6 +1487,95 @@ class Starship:
 #        ^ punctuation.separator.annotation.variable.python
 #                                   ^ keyword.operator.assignment
 
+# Type comments - type: ignore must be by itself.
+
+primes = 5  # type: ignore # type: not-a-type-comment
+#           ^^^^^^^^^^^^^^^ comment.line.type-hint - comment.line.number-sign
+#           ^ punctuation.definition.comment
+#             ^^^^ keyword.other.annotation.type-comment
+#                 ^ punctuation.separator.annotation.type-comment
+#                   ^^^^^^ keyword.other.annotation.type-comment.ignore
+#                          ^^^^^^^^^^^^^^^^^^^^^^^^^^ comment.line.number-sign - comment.line.type-hint
+#                          ^ punctuation.definition.comment
+
+# This is not a type-ignore comment.
+value = 3  # type: ignore_class_starting_with_ignore
+#          ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ comment.line.type-hint - comment.line.number-sign
+#          ^ punctuation.definition.comment
+#            ^^^^ keyword.other.annotation.type-comment
+#                ^ punctuation.separator.annotation.type-comment
+#                  ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ support.class
+
+# Mypy ignore extension
+value = 3  # type: ignore[error-code-1, 4noint][error] # foo
+#          ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ comment.line.type-hint - comment.line.number-sign
+#                  ^^^^^^ keyword.other.annotation.type-comment.ignore
+#                        ^ punctuation.section.brackets.begin
+#                         ^^^^^^^^^^^^ constant.other.error-code
+#                                     ^ punctuation.separator.sequence
+#                                       ^^^^^^ invalid.illegal
+#                                             ^ punctuation.section.brackets.end
+#                                              ^^^^^^^ invalid.illegal
+#                                                      ^^^^^ comment.line.number-sign - comment.line.type-hint
+
+# With/for allow commas
+for a, b in lst: # type: (str, int)
+#                            ^ comment.line.type-hint punctuation.separator.sequence
+
+
+primes = 5  # type: List[Dict[property:str, ...]] # comment
+#           ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ comment.line.type-hint - comment.line.number-sign
+#           ^ punctuation.definition.comment
+#             ^^^^ keyword.other.annotation.type-comment
+#                 ^ punctuation.separator.annotation.type-comment
+#                   ^^^^ support.class
+#                       ^^^^^^^^^^^^^^^^^^^^^^^^^ meta.item-access
+#                       ^punctuation.section.brackets.begin
+#                        ^^^^^^^^^^^^^^^^^^^^^^^ meta.item-access.arguments
+#                        ^^^^ support.class
+#                            ^ meta.item-access punctuation.section.brackets.begin
+#                             ^^^^^^^^ support.function.builtin
+#                                     ^ punctuation.separator.slice
+#                                      ^^^ support.type
+#                                         ^ punctuation.separator.sequence
+#                                           ^^^ constant.language
+#                                              ^ punctuation.section.brackets.end
+#                                               ^ punctuation.section.brackets.end
+#                                                 ^^^^^^^^^^ comment.line.number-sign
+#                                                 ^ punctuation.definition.comment
+
+# Python 2.7 function annotations.
+def function(a, b, *c, **d):
+    # type: (int, str, List[str], bool) -> Dict[str, str] # type: noncomment
+#   ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ comment.line.type-hint
+#           ^ punctuation.section.parens.begin
+#            ^^^ meta.function.parameters support.type
+#               ^ meta.function.parameters punctuation.separator.sequence
+#                      ^^^^ meta.function.parameters support.class
+#                                 ^^^^ meta.function.parameters support.type
+#                                     ^ punctuation.section.parens.end
+#                                       ^^^^^^^^^^^^^^^^^^ meta.function.return-type
+#                                       ^^ punctuation.separator.sequence
+#                                          ^^^^ support.class
+#                                                         ^^^^^^^^^^^^^^^^^^ comment.line.number-sign - comment.line.type-hint
+#                                                         ^ punctuation.definition.comment
+
+class TypeCommentTest:
+    member = []  # type: List[dict]
+
+    def __del__(self) -> None:
+#                        ^^^^ constant.language
+#                            ^ punctuation.section
+        pass
+#       ^^^^ keyword.control
+
+class TypeCommentTest2:
+    member = []  # type: List[dict]
+
+    def __del__(self) -> None:
+        pass
+#       ^^^^ keyword.control
+
 
 ##################
 # Assignment Expressions