diff --git a/language/syntaxes/expressions.tmGrammar.json b/language/syntaxes/expressions.tmGrammar.json
index 6e4fe280..b97c1350 100644
--- a/language/syntaxes/expressions.tmGrammar.json
+++ b/language/syntaxes/expressions.tmGrammar.json
@@ -3,43 +3,76 @@
   "injectionSelector": "L:source.github-actions-workflow",
   "patterns": [
     {
-      "include": "#expression"
+      "include": "#block-inline-expression"
+    },
+    {
+      "include": "#block-if-expression"
     },
     {
       "include": "#if-expression"
     }
   ],
   "repository": {
-    "expression": {
-      "match": "[|-]?\\$\\{\\{(.*?)\\}\\}",
+    "block-inline-expression": {
       "name": "meta.embedded.block.github-actions-expression",
-      "captures": {
+      "begin": "[|-]?\\$\\{\\{",
+      "end": "\\}\\}",
+      "patterns": [
+        {
+          "include": "#expression"
+        }
+      ]
+    },
+    "block-if-expression": {
+      "contentName": "meta.embedded.block.github-actions-expression",
+      "begin": "^\\s*\\b(if:) (?:(\\|)|(>))([1-9])?([-+])?(.*\\n?)",
+      "beginCaptures": {
         "1": {
           "patterns": [
             {
-              "include": "#function-call"
-            },
-            {
-              "include": "#context"
-            },
-            {
-              "include": "#string"
-            },
+              "include": "source.github-actions-workflow"
+            }
+          ]
+        },
+        "2": {
+          "name": "keyword.control.flow.block-scalar.literal.yaml"
+        },
+        "3": {
+          "name": "keyword.control.flow.block-scalar.folded.yaml"
+        },
+        "4": {
+          "name": "constant.numeric.indentation-indicator.yaml"
+        },
+        "5": {
+          "name": "storage.modifier.chomping-indicator.yaml"
+        },
+        "6": {
+          "patterns": [
             {
-              "include": "#number"
+              "include": "#comment"
             },
             {
-              "include": "#boolean"
-            },
+              "match": ".+",
+              "name": "invalid.illegal.expected-comment-or-newline.yaml"
+            }
+          ]
+        }
+      },
+      "end": "^(?=\\S)|(?!\\G)",
+      "patterns": [
+        {
+          "begin": "^([ ]+)(?! )",
+          "end": "^(?!\\1|\\s*$)",
+          "patterns": [
             {
-              "include": "#null"
+              "include": "#expression"
             }
           ]
         }
-      }
+      ]
     },
     "if-expression": {
-      "match": "\\b(if:) (.*?)$",
+      "match": "^\\s*\\b(if:) (.*?)$",
       "contentName": "meta.embedded.block.github-actions-expression",
       "captures": {
         "1": {
@@ -52,27 +85,40 @@
         "2": {
           "patterns": [
             {
-              "include": "#function-call"
-            },
-            {
-              "include": "#context"
-            },
-            {
-              "include": "#string"
-            },
-            {
-              "include": "#number"
-            },
-            {
-              "include": "#boolean"
-            },
-            {
-              "include": "#null"
+              "include": "#expression"
             }
           ]
         }
       }
     },
+    "expression": {
+      "patterns": [
+        {
+          "include": "#function-call"
+        },
+        {
+          "include": "#context"
+        },
+        {
+          "include": "#string"
+        },
+        {
+          "include": "#op-comparison"
+        },
+        {
+          "include": "#op-logical"
+        },
+        {
+          "include": "#number"
+        },
+        {
+          "include": "#boolean"
+        },
+        {
+          "include": "#null"
+        }
+      ]
+    },
     "function-call": {
       "patterns": [
         {
@@ -98,6 +144,14 @@
       "begin": "'",
       "end": "'"
     },
+    "op-comparison": {
+      "name": "keyword.operator.comparison.github-actions-expression",
+      "match": "(==|!=)"
+    },
+    "op-logical": {
+      "name": "keyword.operator.logical.github-actions-expression",
+      "match": "(&&|\\|\\|)"
+    },
     "number": {
       "name": "constant.numeric.github-actions-expression",
       "match": "\\b[0-9]+(?:.[0-9]+)?\\b"