diff --git a/extensions/yaml/cgmanifest.json b/extensions/yaml/cgmanifest.json
index c75a4e52f89ca..18882ead40a00 100644
--- a/extensions/yaml/cgmanifest.json
+++ b/extensions/yaml/cgmanifest.json
@@ -6,7 +6,7 @@
 				"git": {
 					"name": "RedCMD/YAML-Syntax-Highlighter",
 					"repositoryUrl": "https://github.com/RedCMD/YAML-Syntax-Highlighter",
-					"commitHash": "60e2e6e24c63d5a703cb04577678a2e416edd956"
+					"commitHash": "d4dca9f38a654ebbb13c1b72b7881e3c5864a778"
 				}
 			},
 			"licenseDetail": [
@@ -21,7 +21,7 @@
 				"THE SOFTWARE IS PROVIDED “AS IS”, WITHOUT WARRANTY OF ANY KIND, EXPRESS OR IMPLIED, INCLUDING BUT NOT LIMITED TO THE WARRANTIES OF MERCHANTABILITY, FITNESS FOR A PARTICULAR PURPOSE AND NONINFRINGEMENT. IN NO EVENT SHALL THE AUTHORS OR COPYRIGHT HOLDERS BE LIABLE FOR ANY CLAIM, DAMAGES OR OTHER LIABILITY, WHETHER IN AN ACTION OF CONTRACT, TORT OR OTHERWISE, ARISING FROM, OUT OF OR IN CONNECTION WITH THE SOFTWARE OR THE USE OR OTHER DEALINGS IN THE SOFTWARE."
 			],
 			"license": "MIT",
-			"version": "1.0.1"
+			"version": "1.1.1"
 		}
 	],
 	"version": 1
diff --git a/extensions/yaml/syntaxes/yaml-1.0.tmLanguage.json b/extensions/yaml/syntaxes/yaml-1.0.tmLanguage.json
index 6ca3d9bf1b89b..7ae77112860c3 100644
--- a/extensions/yaml/syntaxes/yaml-1.0.tmLanguage.json
+++ b/extensions/yaml/syntaxes/yaml-1.0.tmLanguage.json
@@ -4,7 +4,7 @@
 		"If you want to provide a fix or improvement, please create a pull request against the original repository.",
 		"Once accepted there, we are happy to receive an update request."
 	],
-	"version": "https://github.com/RedCMD/YAML-Syntax-Highlighter/commit/60e2e6e24c63d5a703cb04577678a2e416edd956",
+	"version": "https://github.com/RedCMD/YAML-Syntax-Highlighter/commit/dfd7e5f4f71f9695c5d8697ca57f81240165aa04",
 	"name": "YAML 1.0",
 	"scopeName": "source.yaml.1.0",
 	"comment": "https://yaml.org/spec/1.0/",
@@ -500,7 +500,8 @@
 		},
 		"block-map-value": {
 			"comment": "https://yaml.org/spec/1.2.2/#rule-c-l-block-map-implicit-value",
-			"begin": ":(?=[\\x{85 2028 2029}\r\n\t ])",
+			"//": "Assumming 3rd party preprocessing variables `{{...}}` turn into valid map-keys when inside a block-mapping",
+			"begin": ":(?=[\\x{85 2028 2029}\r\n\t ])|(?<=}})(?=[\t ]++#|[\t ]*+$)",
 			"while": "\\G(?![?:!\"'0-9A-Za-z$()+./;<=\\\\^_~\\[{\\x{A0}-\\x{D7FF}\\x{E000}-\\x{FFFD}\\x{010000}-\\x{10FFFF}&&[^\\x{2028 2029}]]|-[^\\x{85 2028 2029}\r\n\t ])",
 			"beginCaptures": {
 				"0": {
diff --git a/extensions/yaml/syntaxes/yaml-1.1.tmLanguage.json b/extensions/yaml/syntaxes/yaml-1.1.tmLanguage.json
index 3b7974a1a5dfd..57a96ac1e4fd4 100644
--- a/extensions/yaml/syntaxes/yaml-1.1.tmLanguage.json
+++ b/extensions/yaml/syntaxes/yaml-1.1.tmLanguage.json
@@ -4,7 +4,7 @@
 		"If you want to provide a fix or improvement, please create a pull request against the original repository.",
 		"Once accepted there, we are happy to receive an update request."
 	],
-	"version": "https://github.com/RedCMD/YAML-Syntax-Highlighter/commit/60e2e6e24c63d5a703cb04577678a2e416edd956",
+	"version": "https://github.com/RedCMD/YAML-Syntax-Highlighter/commit/dfd7e5f4f71f9695c5d8697ca57f81240165aa04",
 	"name": "YAML 1.1",
 	"scopeName": "source.yaml.1.1",
 	"comment": "https://yaml.org/spec/1.1/",
@@ -641,7 +641,8 @@
 		},
 		"block-map-value": {
 			"comment": "https://yaml.org/spec/1.2.2/#rule-c-l-block-map-implicit-value",
-			"begin": ":(?=[\\x{85 2028 2029}\r\n\t ])",
+			"//": "Assumming 3rd party preprocessing variables `{{...}}` turn into valid map-keys when inside a block-mapping",
+			"begin": ":(?=[\\x{85 2028 2029}\r\n\t ])|(?<=}})(?=[\t ]++#|[\t ]*+$)",
 			"while": "\\G(?![?:!\"'0-9A-Za-z$()+./;<=\\\\^_~\\[{\\x{A0}-\\x{D7FF}\\x{E000}-\\x{FFFD}\\x{010000}-\\x{10FFFF}&&[^\\x{2028 2029}]]|-[^\\x{85 2028 2029}\r\n\t ])",
 			"beginCaptures": {
 				"0": {
diff --git a/extensions/yaml/syntaxes/yaml-1.2.tmLanguage.json b/extensions/yaml/syntaxes/yaml-1.2.tmLanguage.json
index 711f5c8e4222f..965b604081667 100644
--- a/extensions/yaml/syntaxes/yaml-1.2.tmLanguage.json
+++ b/extensions/yaml/syntaxes/yaml-1.2.tmLanguage.json
@@ -4,7 +4,7 @@
 		"If you want to provide a fix or improvement, please create a pull request against the original repository.",
 		"Once accepted there, we are happy to receive an update request."
 	],
-	"version": "https://github.com/RedCMD/YAML-Syntax-Highlighter/commit/60e2e6e24c63d5a703cb04577678a2e416edd956",
+	"version": "https://github.com/RedCMD/YAML-Syntax-Highlighter/commit/d4dca9f38a654ebbb13c1b72b7881e3c5864a778",
 	"name": "YAML 1.2",
 	"scopeName": "source.yaml.1.2",
 	"comment": "https://yaml.org/spec/1.2.2",
@@ -37,6 +37,7 @@
 					]
 				},
 				{
+					"comment": "For when YAML is embedded inside a Markdown code-block",
 					"begin": "\\G",
 					"while": "\\G",
 					"name": "meta.stream.yaml",
@@ -633,7 +634,8 @@
 		},
 		"block-map-value": {
 			"comment": "https://yaml.org/spec/1.2.2/#rule-c-l-block-map-implicit-value",
-			"begin": ":(?=[\r\n\t ])",
+			"//": "Assumming 3rd party preprocessing variables `{{...}}` turn into valid map-keys when inside a block-mapping",
+			"begin": ":(?=[\r\n\t ])|(?<=}})(?=[\t ]++#|[\t ]*+$)",
 			"while": "\\G(?![?:!\"'0-9A-Za-z$()+./;<=\\\\^_~\\[{\\x{85}\\x{A0}-\\x{D7FF}\\x{E000}-\\x{FFFD}\\x{010000}-\\x{10FFFF}&&[^\\x{FEFF}]]|-[^\r\n\t ])",
 			"beginCaptures": {
 				"0": {
diff --git a/extensions/yaml/syntaxes/yaml.tmLanguage.json b/extensions/yaml/syntaxes/yaml.tmLanguage.json
index 8be76d7a3c595..3a64fbd850e07 100644
--- a/extensions/yaml/syntaxes/yaml.tmLanguage.json
+++ b/extensions/yaml/syntaxes/yaml.tmLanguage.json
@@ -4,10 +4,21 @@
 		"If you want to provide a fix or improvement, please create a pull request against the original repository.",
 		"Once accepted there, we are happy to receive an update request."
 	],
-	"version": "https://github.com/RedCMD/YAML-Syntax-Highlighter/commit/274009903e20ac6dc37ba5763fb853744e28c9b2",
+	"version": "https://github.com/RedCMD/YAML-Syntax-Highlighter/commit/d4dca9f38a654ebbb13c1b72b7881e3c5864a778",
 	"name": "YAML Ain't Markup Language",
 	"scopeName": "source.yaml",
 	"patterns": [
+		{
+			"comment": "Support legacy FrontMatter integration",
+			"//": "https://github.com/microsoft/vscode-markdown-tm-grammar/pull/162",
+			"begin": "(?<=^-{3,}\\s*+)\\G$",
+			"while": "^(?! {3,0}-{3,}[ \t]*+$|[ \t]*+\\.{3}$)",
+			"patterns": [
+				{
+					"include": "source.yaml.1.2"
+				}
+			]
+		},
 		{
 			"comment": "Default to YAML version 1.2",
 			"include": "source.yaml.1.2"