diff --git a/vscode/grammars/ruby.cson.json b/vscode/grammars/ruby.cson.json
index 7be523fa8..2c7b83a0c 100644
--- a/vscode/grammars/ruby.cson.json
+++ b/vscode/grammars/ruby.cson.json
@@ -109,20 +109,23 @@
           "name": "keyword.operator.assignment.augmented.ruby"
         }
       },
-      "match": "^\\s*([a-z]([A-Za-z0-9_])*)\\s*(&&=)",
-      "comment": "A local variable and assignment"
+      "match": "^\\s*([a-z]([A-Za-z0-9_])*)\\s*((&&|\\|\\|)=)",
+      "comment": "A local variable and/or assignment"
     },
     {
       "captures": {
         "1": {
-          "name": "variable.ruby"
+          "name": "keyword.control.ruby"
         },
         "3": {
+          "name": "variable.ruby"
+        },
+        "5": {
           "name": "keyword.operator.assignment.augmented.ruby"
         }
       },
-      "match": "^\\s*([a-z]([A-Za-z0-9_])*)\\s*(\\|\\|=)",
-      "comment": "A local variable or assignment"
+      "match": "(?<!\\.)\\b(case|if|elsif|unless|until|while)\\b\\s*(\\()*?\\s*([a-z]([A-Za-z0-9_])*)\\s*((&&|\\|\\|)=)",
+      "comment": "A local variable and/or assignment in a condition"
     },
     {
       "captures": {
@@ -136,6 +139,21 @@
       "match": "^\\s*([a-z]([A-Za-z0-9_])*)\\s*((\\+|\\*|-|\\/|%|\\*\\*|&|\\||\\^|<<|>>)=)",
       "comment": "A local variable operation assignment (+=, -=, *=, /=)"
     },
+    {
+      "captures": {
+        "1": {
+          "name": "keyword.control.ruby"
+        },
+        "3": {
+          "name": "variable.ruby"
+        },
+        "5": {
+          "name": "keyword.operator.assignment.augmented.ruby"
+        }
+      },
+      "match": "(?<!\\.)\\b(case|if|elsif|unless|until|while)\\b\\s*(\\()*?\\s*([a-z]([A-Za-z0-9_])*)\\s*((\\+|\\*|-|\\/|%|\\*\\*|&|\\||\\^|<<|>>)=)",
+      "comment": "A local variable operation assignment in a condition"
+    },
     {
       "captures": {
         "1": {
@@ -145,6 +163,18 @@
       "match": "^\\s*([a-z]([A-Za-z0-9_])*)\\s*=[^=>]",
       "comment": "A local variable assignment"
     },
+    {
+      "captures": {
+        "1": {
+          "name": "keyword.control.ruby"
+        },
+        "3": {
+          "name": "variable.ruby"
+        }
+      },
+      "match": "(?<!\\.)\\b(case|if|elsif|unless|until|while)\\b\\s*(\\()*?\\s*([a-z]([A-Za-z0-9_])*)\\s*=[^=>]",
+      "comment": "A local variable assignment in a condition"
+    },
     {
       "captures": {
         "1": {
diff --git a/vscode/src/test/suite/grammars.test.ts b/vscode/src/test/suite/grammars.test.ts
index 127f1e963..6cc2065f4 100644
--- a/vscode/src/test/suite/grammars.test.ts
+++ b/vscode/src/test/suite/grammars.test.ts
@@ -337,6 +337,66 @@ suite("Grammars", () => {
         const actualTokens = tokenizeRuby(ruby);
         assert.deepStrictEqual(actualTokens, expectedTokens);
       });
+      test("or assignment", () => {
+        const ruby = "local ||= 1";
+        const expectedTokens = [
+          ["local", ["source.ruby", "variable.ruby"]],
+          [" ", ["source.ruby"]],
+          [
+            "||=",
+            ["source.ruby", "keyword.operator.assignment.augmented.ruby"],
+          ],
+          [" ", ["source.ruby"]],
+          ["1", ["source.ruby", "constant.numeric.ruby"]],
+        ];
+        const actualTokens = tokenizeRuby(ruby);
+        assert.deepStrictEqual(actualTokens, expectedTokens);
+      });
+      test("and assignment in a condition", () => {
+        const ruby = "if local &&= 1";
+        const expectedTokens = [
+          ["if", ["source.ruby", "keyword.control.ruby"]],
+          [" ", ["source.ruby"]],
+          ["local", ["source.ruby", "variable.ruby"]],
+          [" ", ["source.ruby"]],
+          [
+            "&&=",
+            ["source.ruby", "keyword.operator.assignment.augmented.ruby"],
+          ],
+          [" ", ["source.ruby"]],
+          ["1", ["source.ruby", "constant.numeric.ruby"]],
+        ];
+        const actualTokens = tokenizeRuby(ruby);
+        assert.deepStrictEqual(actualTokens, expectedTokens);
+      });
+      test("assignment in a condition", () => {
+        const ruby = "if (local = 1)";
+        const expectedTokens = [
+          ["if", ["source.ruby", "keyword.control.ruby"]],
+          [" (", ["source.ruby"]],
+          ["local", ["source.ruby", "variable.ruby"]],
+          [" = ", ["source.ruby"]],
+          ["1", ["source.ruby", "constant.numeric.ruby"]],
+          [")", ["source.ruby", "punctuation.section.function.ruby"]],
+        ];
+        const actualTokens = tokenizeRuby(ruby);
+        assert.deepStrictEqual(actualTokens, expectedTokens);
+      });
+      test("operation assignment in a condition", () => {
+        const ruby = "if (local += 1)";
+        const expectedTokens = [
+          ["if", ["source.ruby", "keyword.control.ruby"]],
+          [" (", ["source.ruby"]],
+          ["local", ["source.ruby", "variable.ruby"]],
+          [" ", ["source.ruby"]],
+          ["+=", ["source.ruby", "keyword.operator.assignment.augmented.ruby"]],
+          [" ", ["source.ruby"]],
+          ["1", ["source.ruby", "constant.numeric.ruby"]],
+          [")", ["source.ruby", "punctuation.section.function.ruby"]],
+        ];
+        const actualTokens = tokenizeRuby(ruby);
+        assert.deepStrictEqual(actualTokens, expectedTokens);
+      });
     });
 
     function tokenizeRuby(ruby: string): [string, string[]][] {