diff --git a/Markdown/Markdown.sublime-syntax b/Markdown/Markdown.sublime-syntax
index 7933fe46b6..5ea0be5176 100644
--- a/Markdown/Markdown.sublime-syntax
+++ b/Markdown/Markdown.sublime-syntax
@@ -66,7 +66,9 @@ variables:
               \s*                       # Optional whitespace
           (\))
         )
-    skip_html_tags: '(?:<[^>]+>)'
+    skip_self_closing_html_tags: '(?:<(?:hr|br)\b[^>]*>)'
+    skip_html_tag_content: '(?:<[^>]+[^<]*</[^>]+>)'
+    skip_html_tags: '(?:{{skip_self_closing_html_tags}}|{{skip_html_tag_content}})'
 contexts:
   main:
     - match: |-
@@ -241,7 +243,11 @@ contexts:
                         )
                   | \*{3,}                              # not applicable
                   | [ \t]\*+                            # Match whitespace followed by the style closer because it doesn't close the style
-                  | (?!\*\*).                           # Everything else besides style closer
+                  | (?!
+                        {{skip_html_tags}}              # emulate possessive quantifers by repeating patterns
+                    |   {{backticks}}
+                    |   {{escape}}
+                    |   \*\*).                          # Everything else besides style closer
                 )+
                 \*\*                                    # Close
             )
@@ -262,7 +268,7 @@ contexts:
         - include: italic
     - match: |-
         (?x)
-            (\b__)(?=\S)(?!_)                              # Open
+            (\b__)(?=\S)(?!_)                           # Open
             (?=
                 (?:
                     {{skip_html_tags}}                  # HTML tags
@@ -278,7 +284,11 @@ contexts:
                         )
                   | _{3,}                                # not applicable
                   | [ \t]_+                              # Match whitespace followed by the style closer because it doesn't close the style
-                  | (?!__).                              # Everything else besides style closer
+                  | (?!
+                        {{skip_html_tags}}               # emulate possessive quantifers by repeating patterns
+                    |   {{backticks}}
+                    |   {{escape}}
+                    |   __).                             # Everything else besides style closer
                 )+
                 __                                       # Close
             )
@@ -426,7 +436,11 @@ contexts:
                         )
                   | \*{2,}                              # Must be bold opener or closer or not applicable
                   | [ \t]\*+                            # Match whitespace followed by the style closer because it doesn't close the style
-                  | (?!\*).                             # Everything else besides style closer
+                  | (?!
+                        {{skip_html_tags}}              # emulate possessive quantifers by repeating patterns
+                    |   {{backticks}}
+                    |   {{escape}}
+                    |   \*).                            # Everything else besides style closer
                 )+
                 \*                                      # Close
             )
@@ -447,7 +461,7 @@ contexts:
         - include: bold
     - match: |-
         (?x)
-            (\b_)(?=\S)(?!_)                              # Open
+            (\b_)(?=\S)(?!_)                            # Open
             (?=
                 (?:
                     {{skip_html_tags}}                  # HTML tags
@@ -463,7 +477,11 @@ contexts:
                         )
                   | _{2,}                               # Must be bold opener or closer or not applicable
                   | [ \t]_+                             # Match whitespace followed by the style closer because it doesn't close the style
-                  | (?!_).                              # Everything else besides style closer
+                  | (?!
+                        {{skip_html_tags}}              # emulate possessive quantifers by repeating patterns
+                    |   {{backticks}}
+                    |   {{escape}}
+                    |   _).                             # Everything else besides style closer
                 )+
                 _                                       # Close
             )
@@ -475,7 +493,6 @@ contexts:
               (?x)
                   [ \t]*_{3,}   # if there are more than 3 its not applicable to be bold or italic
               |   [ \t]+_(?!_)  # whitespace followed by 1 is also not applicable (but whitespace followed by 2 could be bold punctuation)
-        
         - match: (\1)(?!\1)
           captures:
             1: punctuation.definition.italic.end.markdown
diff --git a/Markdown/syntax_test_markdown.md b/Markdown/syntax_test_markdown.md
index 0c49c818b6..4cf978becd 100644
--- a/Markdown/syntax_test_markdown.md
+++ b/Markdown/syntax_test_markdown.md
@@ -465,3 +465,42 @@ more _tests <span class="test_">here</span>_
 |    ^ punctuation.definition.italic.begin
 |                            ^ - punctuation.definition
 |                                          ^ punctuation.definition.italic.end
+_more `tests_` here_
+| <- punctuation.definition.italic.begin
+|     ^^^^^^^^ markup.raw.inline
+|                  ^ punctuation.definition.italic.end
+__more `tests__` here__
+| <- punctuation.definition.bold.begin
+|      ^^^^^^^^^ markup.raw.inline
+|                    ^^ punctuation.definition.bold.end
+_test <span>text_ not formatted</span>
+| <- - punctuation
+|               ^ - punctuation
+__test <span>text__ not formatted</span>
+| <- - punctuation
+|                ^^ - punctuation
+*test <span>text* not formatted</span>
+| <- - punctuation
+|               ^ - punctuation
+**test <span>text** not formatted</span>
+| <- - punctuation
+|                ^^ - punctuation
+_test <span>text **formatted**</span>_
+| <- punctuation
+|                ^^ punctuation
+|                           ^^ punctuation
+|                                    ^ punctuation
+*test <span>text __formatted__</span>*
+| <- punctuation
+|                ^^ punctuation
+|                           ^^ punctuation
+|                                    ^ punctuation
+*test <span>text __formatted__</span>* **more** _text_
+| <- punctuation
+|                ^^ punctuation
+|                           ^^ punctuation
+|                                    ^ punctuation
+|                                      ^^ punctuation
+|                                            ^^ punctuation
+|                                               ^ punctuation
+|                                                    ^ punctuation