diff --git a/extensions/markdown/syntaxes/markdown.tmLanguage b/extensions/markdown/syntaxes/markdown.tmLanguage
index d9429dcf6a0..f6f109289f2 100644
--- a/extensions/markdown/syntaxes/markdown.tmLanguage
+++ b/extensions/markdown/syntaxes/markdown.tmLanguage
@@ -354,11 +354,11 @@
 										</dict>
 									</array>
 									<key>while</key>
-									<string>^\s*(?!&lt;/(script|style|pre)&gt;)</string>
+									<string>^(?!.*&lt;/(script|style|pre)&gt;)</string>
 								</dict>
 							</array>
 							<key>end</key>
-							<string>(?=&lt;/(script|style|pre)&gt;)</string>
+							<string>(?=.*&lt;/(script|style|pre)&gt;)</string>
 						</dict>
 						<dict>
 							<key>begin</key>
diff --git a/extensions/markdown/syntaxes/markdown.tmLanguage.base b/extensions/markdown/syntaxes/markdown.tmLanguage.base
index 4783abf8b0f..6d0a8510217 100644
--- a/extensions/markdown/syntaxes/markdown.tmLanguage.base
+++ b/extensions/markdown/syntaxes/markdown.tmLanguage.base
@@ -179,11 +179,11 @@
 										</dict>
 									</array>
 									<key>while</key>
-									<string>^\s*(?!&lt;/(script|style|pre)&gt;)</string>
+									<string>^(?!.*&lt;/(script|style|pre)&gt;)</string>
 								</dict>
 							</array>
 							<key>end</key>
-							<string>(?=&lt;/(script|style|pre)&gt;)</string>
+							<string>(?=.*&lt;/(script|style|pre)&gt;)</string>
 						</dict>
 						<dict>
 							<key>begin</key>
diff --git a/extensions/markdown/test/colorize-fixtures/test-33886.md b/extensions/markdown/test/colorize-fixtures/test-33886.md
new file mode 100644
index 00000000000..472c4a76498
--- /dev/null
+++ b/extensions/markdown/test/colorize-fixtures/test-33886.md
@@ -0,0 +1,13 @@
+# h
+
+<pre><code>
+# a
+</code></pre>
+
+# h
+
+<pre>
+# a
+a</pre>
+
+# h
\ No newline at end of file
diff --git a/extensions/markdown/test/colorize-results/test-33886_md.json b/extensions/markdown/test/colorize-results/test-33886_md.json
new file mode 100644
index 00000000000..ed8d6a43aaa
--- /dev/null
+++ b/extensions/markdown/test/colorize-results/test-33886_md.json
@@ -0,0 +1,332 @@
+[
+	{
+		"c": "#",
+		"t": "text.html.markdown markup.heading.markdown punctuation.definition.heading.markdown",
+		"r": {
+			"dark_plus": "markup.heading: #569CD6",
+			"light_plus": "markup.heading: #800000",
+			"dark_vs": "markup.heading: #569CD6",
+			"light_vs": "markup.heading: #800000",
+			"hc_black": "markup.heading: #6796E6"
+		}
+	},
+	{
+		"c": " ",
+		"t": "text.html.markdown markup.heading.markdown",
+		"r": {
+			"dark_plus": "markup.heading: #569CD6",
+			"light_plus": "markup.heading: #800000",
+			"dark_vs": "markup.heading: #569CD6",
+			"light_vs": "markup.heading: #800000",
+			"hc_black": "markup.heading: #6796E6"
+		}
+	},
+	{
+		"c": "h",
+		"t": "text.html.markdown markup.heading.markdown entity.name.section.markdown",
+		"r": {
+			"dark_plus": "markup.heading: #569CD6",
+			"light_plus": "markup.heading: #800000",
+			"dark_vs": "markup.heading: #569CD6",
+			"light_vs": "markup.heading: #800000",
+			"hc_black": "markup.heading: #6796E6"
+		}
+	},
+	{
+		"c": "<",
+		"t": "text.html.markdown meta.tag.block.any.html punctuation.definition.tag.begin.html",
+		"r": {
+			"dark_plus": "punctuation.definition.tag: #808080",
+			"light_plus": "punctuation.definition.tag: #800000",
+			"dark_vs": "punctuation.definition.tag: #808080",
+			"light_vs": "punctuation.definition.tag: #800000",
+			"hc_black": "punctuation.definition.tag: #808080"
+		}
+	},
+	{
+		"c": "pre",
+		"t": "text.html.markdown meta.tag.block.any.html entity.name.tag.block.any.html",
+		"r": {
+			"dark_plus": "entity.name.tag: #569CD6",
+			"light_plus": "entity.name.tag: #800000",
+			"dark_vs": "entity.name.tag: #569CD6",
+			"light_vs": "entity.name.tag: #800000",
+			"hc_black": "entity.name.tag: #569CD6"
+		}
+	},
+	{
+		"c": ">",
+		"t": "text.html.markdown meta.tag.block.any.html punctuation.definition.tag.end.html",
+		"r": {
+			"dark_plus": "punctuation.definition.tag: #808080",
+			"light_plus": "punctuation.definition.tag: #800000",
+			"dark_vs": "punctuation.definition.tag: #808080",
+			"light_vs": "punctuation.definition.tag: #800000",
+			"hc_black": "punctuation.definition.tag: #808080"
+		}
+	},
+	{
+		"c": "<",
+		"t": "text.html.markdown meta.tag.inline.any.html punctuation.definition.tag.begin.html",
+		"r": {
+			"dark_plus": "punctuation.definition.tag: #808080",
+			"light_plus": "punctuation.definition.tag: #800000",
+			"dark_vs": "punctuation.definition.tag: #808080",
+			"light_vs": "punctuation.definition.tag: #800000",
+			"hc_black": "punctuation.definition.tag: #808080"
+		}
+	},
+	{
+		"c": "code",
+		"t": "text.html.markdown meta.tag.inline.any.html entity.name.tag.inline.any.html",
+		"r": {
+			"dark_plus": "entity.name.tag: #569CD6",
+			"light_plus": "entity.name.tag: #800000",
+			"dark_vs": "entity.name.tag: #569CD6",
+			"light_vs": "entity.name.tag: #800000",
+			"hc_black": "entity.name.tag: #569CD6"
+		}
+	},
+	{
+		"c": ">",
+		"t": "text.html.markdown meta.tag.inline.any.html punctuation.definition.tag.end.html",
+		"r": {
+			"dark_plus": "punctuation.definition.tag: #808080",
+			"light_plus": "punctuation.definition.tag: #800000",
+			"dark_vs": "punctuation.definition.tag: #808080",
+			"light_vs": "punctuation.definition.tag: #800000",
+			"hc_black": "punctuation.definition.tag: #808080"
+		}
+	},
+	{
+		"c": "# a",
+		"t": "text.html.markdown",
+		"r": {
+			"dark_plus": "default: #D4D4D4",
+			"light_plus": "default: #000000",
+			"dark_vs": "default: #D4D4D4",
+			"light_vs": "default: #000000",
+			"hc_black": "default: #FFFFFF"
+		}
+	},
+	{
+		"c": "</",
+		"t": "text.html.markdown meta.paragraph.markdown meta.tag.inline.any.html punctuation.definition.tag.begin.html",
+		"r": {
+			"dark_plus": "punctuation.definition.tag: #808080",
+			"light_plus": "punctuation.definition.tag: #800000",
+			"dark_vs": "punctuation.definition.tag: #808080",
+			"light_vs": "punctuation.definition.tag: #800000",
+			"hc_black": "punctuation.definition.tag: #808080"
+		}
+	},
+	{
+		"c": "code",
+		"t": "text.html.markdown meta.paragraph.markdown meta.tag.inline.any.html entity.name.tag.inline.any.html",
+		"r": {
+			"dark_plus": "entity.name.tag: #569CD6",
+			"light_plus": "entity.name.tag: #800000",
+			"dark_vs": "entity.name.tag: #569CD6",
+			"light_vs": "entity.name.tag: #800000",
+			"hc_black": "entity.name.tag: #569CD6"
+		}
+	},
+	{
+		"c": ">",
+		"t": "text.html.markdown meta.paragraph.markdown meta.tag.inline.any.html punctuation.definition.tag.end.html",
+		"r": {
+			"dark_plus": "punctuation.definition.tag: #808080",
+			"light_plus": "punctuation.definition.tag: #800000",
+			"dark_vs": "punctuation.definition.tag: #808080",
+			"light_vs": "punctuation.definition.tag: #800000",
+			"hc_black": "punctuation.definition.tag: #808080"
+		}
+	},
+	{
+		"c": "</",
+		"t": "text.html.markdown meta.paragraph.markdown meta.tag.block.any.html punctuation.definition.tag.begin.html",
+		"r": {
+			"dark_plus": "punctuation.definition.tag: #808080",
+			"light_plus": "punctuation.definition.tag: #800000",
+			"dark_vs": "punctuation.definition.tag: #808080",
+			"light_vs": "punctuation.definition.tag: #800000",
+			"hc_black": "punctuation.definition.tag: #808080"
+		}
+	},
+	{
+		"c": "pre",
+		"t": "text.html.markdown meta.paragraph.markdown meta.tag.block.any.html entity.name.tag.block.any.html",
+		"r": {
+			"dark_plus": "entity.name.tag: #569CD6",
+			"light_plus": "entity.name.tag: #800000",
+			"dark_vs": "entity.name.tag: #569CD6",
+			"light_vs": "entity.name.tag: #800000",
+			"hc_black": "entity.name.tag: #569CD6"
+		}
+	},
+	{
+		"c": ">",
+		"t": "text.html.markdown meta.paragraph.markdown meta.tag.block.any.html punctuation.definition.tag.end.html",
+		"r": {
+			"dark_plus": "punctuation.definition.tag: #808080",
+			"light_plus": "punctuation.definition.tag: #800000",
+			"dark_vs": "punctuation.definition.tag: #808080",
+			"light_vs": "punctuation.definition.tag: #800000",
+			"hc_black": "punctuation.definition.tag: #808080"
+		}
+	},
+	{
+		"c": "#",
+		"t": "text.html.markdown markup.heading.markdown punctuation.definition.heading.markdown",
+		"r": {
+			"dark_plus": "markup.heading: #569CD6",
+			"light_plus": "markup.heading: #800000",
+			"dark_vs": "markup.heading: #569CD6",
+			"light_vs": "markup.heading: #800000",
+			"hc_black": "markup.heading: #6796E6"
+		}
+	},
+	{
+		"c": " ",
+		"t": "text.html.markdown markup.heading.markdown",
+		"r": {
+			"dark_plus": "markup.heading: #569CD6",
+			"light_plus": "markup.heading: #800000",
+			"dark_vs": "markup.heading: #569CD6",
+			"light_vs": "markup.heading: #800000",
+			"hc_black": "markup.heading: #6796E6"
+		}
+	},
+	{
+		"c": "h",
+		"t": "text.html.markdown markup.heading.markdown entity.name.section.markdown",
+		"r": {
+			"dark_plus": "markup.heading: #569CD6",
+			"light_plus": "markup.heading: #800000",
+			"dark_vs": "markup.heading: #569CD6",
+			"light_vs": "markup.heading: #800000",
+			"hc_black": "markup.heading: #6796E6"
+		}
+	},
+	{
+		"c": "<",
+		"t": "text.html.markdown meta.tag.block.any.html punctuation.definition.tag.begin.html",
+		"r": {
+			"dark_plus": "punctuation.definition.tag: #808080",
+			"light_plus": "punctuation.definition.tag: #800000",
+			"dark_vs": "punctuation.definition.tag: #808080",
+			"light_vs": "punctuation.definition.tag: #800000",
+			"hc_black": "punctuation.definition.tag: #808080"
+		}
+	},
+	{
+		"c": "pre",
+		"t": "text.html.markdown meta.tag.block.any.html entity.name.tag.block.any.html",
+		"r": {
+			"dark_plus": "entity.name.tag: #569CD6",
+			"light_plus": "entity.name.tag: #800000",
+			"dark_vs": "entity.name.tag: #569CD6",
+			"light_vs": "entity.name.tag: #800000",
+			"hc_black": "entity.name.tag: #569CD6"
+		}
+	},
+	{
+		"c": ">",
+		"t": "text.html.markdown meta.tag.block.any.html punctuation.definition.tag.end.html",
+		"r": {
+			"dark_plus": "punctuation.definition.tag: #808080",
+			"light_plus": "punctuation.definition.tag: #800000",
+			"dark_vs": "punctuation.definition.tag: #808080",
+			"light_vs": "punctuation.definition.tag: #800000",
+			"hc_black": "punctuation.definition.tag: #808080"
+		}
+	},
+	{
+		"c": "# a",
+		"t": "text.html.markdown",
+		"r": {
+			"dark_plus": "default: #D4D4D4",
+			"light_plus": "default: #000000",
+			"dark_vs": "default: #D4D4D4",
+			"light_vs": "default: #000000",
+			"hc_black": "default: #FFFFFF"
+		}
+	},
+	{
+		"c": "a",
+		"t": "text.html.markdown meta.paragraph.markdown",
+		"r": {
+			"dark_plus": "default: #D4D4D4",
+			"light_plus": "default: #000000",
+			"dark_vs": "default: #D4D4D4",
+			"light_vs": "default: #000000",
+			"hc_black": "default: #FFFFFF"
+		}
+	},
+	{
+		"c": "</",
+		"t": "text.html.markdown meta.paragraph.markdown meta.tag.block.any.html punctuation.definition.tag.begin.html",
+		"r": {
+			"dark_plus": "punctuation.definition.tag: #808080",
+			"light_plus": "punctuation.definition.tag: #800000",
+			"dark_vs": "punctuation.definition.tag: #808080",
+			"light_vs": "punctuation.definition.tag: #800000",
+			"hc_black": "punctuation.definition.tag: #808080"
+		}
+	},
+	{
+		"c": "pre",
+		"t": "text.html.markdown meta.paragraph.markdown meta.tag.block.any.html entity.name.tag.block.any.html",
+		"r": {
+			"dark_plus": "entity.name.tag: #569CD6",
+			"light_plus": "entity.name.tag: #800000",
+			"dark_vs": "entity.name.tag: #569CD6",
+			"light_vs": "entity.name.tag: #800000",
+			"hc_black": "entity.name.tag: #569CD6"
+		}
+	},
+	{
+		"c": ">",
+		"t": "text.html.markdown meta.paragraph.markdown meta.tag.block.any.html punctuation.definition.tag.end.html",
+		"r": {
+			"dark_plus": "punctuation.definition.tag: #808080",
+			"light_plus": "punctuation.definition.tag: #800000",
+			"dark_vs": "punctuation.definition.tag: #808080",
+			"light_vs": "punctuation.definition.tag: #800000",
+			"hc_black": "punctuation.definition.tag: #808080"
+		}
+	},
+	{
+		"c": "#",
+		"t": "text.html.markdown markup.heading.markdown punctuation.definition.heading.markdown",
+		"r": {
+			"dark_plus": "markup.heading: #569CD6",
+			"light_plus": "markup.heading: #800000",
+			"dark_vs": "markup.heading: #569CD6",
+			"light_vs": "markup.heading: #800000",
+			"hc_black": "markup.heading: #6796E6"
+		}
+	},
+	{
+		"c": " ",
+		"t": "text.html.markdown markup.heading.markdown",
+		"r": {
+			"dark_plus": "markup.heading: #569CD6",
+			"light_plus": "markup.heading: #800000",
+			"dark_vs": "markup.heading: #569CD6",
+			"light_vs": "markup.heading: #800000",
+			"hc_black": "markup.heading: #6796E6"
+		}
+	},
+	{
+		"c": "h",
+		"t": "text.html.markdown markup.heading.markdown entity.name.section.markdown",
+		"r": {
+			"dark_plus": "markup.heading: #569CD6",
+			"light_plus": "markup.heading: #800000",
+			"dark_vs": "markup.heading: #569CD6",
+			"light_vs": "markup.heading: #800000",
+			"hc_black": "markup.heading: #6796E6"
+		}
+	}
+]
\ No newline at end of file