diff --git a/.changeset/flat-humans-hammer.md b/.changeset/flat-humans-hammer.md
new file mode 100644
index 00000000..4fe3765c
--- /dev/null
+++ b/.changeset/flat-humans-hammer.md
@@ -0,0 +1,7 @@
+---
+'@vanilla-extract/css': patch
+---
+
+Fixes a bug causing invalid selectors to be generated in some cases
+
+When transforming selectors containing consective copies of the same classname, e.g: `&&`, if `&` was a substring of another local classname and that classname happened to end with the same character that `&` started with, the generated selector would be invalid.
diff --git a/packages/css/src/transformCss.test.ts b/packages/css/src/transformCss.test.ts
index fe9fa25c..f152c871 100644
--- a/packages/css/src/transformCss.test.ts
+++ b/packages/css/src/transformCss.test.ts
@@ -2299,6 +2299,61 @@ describe('transformCss', () => {
       }
     `);
   });
+
+  it('should handle consecutive references to the same classname that is a substring of another classname with the same start and end character', () => {
+    const classname1 = 'debugName_hash1';
+    const classname2 = 'debugName_hash1d';
+
+    expect(
+      transformCss({
+        composedClassLists: [],
+        localClassNames: [classname1, classname2],
+
+        cssObjs: [
+          {
+            type: 'local',
+            selector: classname1,
+            rule: {
+              selectors: {
+                // Bug reproduction
+                ['&&']: {
+                  background: 'black',
+                },
+                // Exhaustive tests for combinations of two adjacent classnames
+                [`${classname2}&`]: {
+                  background: 'orange',
+                },
+                [`&${classname2}&`]: {
+                  background: 'orange',
+                },
+                [`${classname2}${classname2}&`]: {
+                  background: 'orange',
+                },
+              },
+            },
+          },
+          {
+            type: 'local',
+            selector: classname2,
+            rule: {},
+          },
+        ],
+      }).join('\n'),
+    ).toMatchInlineSnapshot(`
+      .debugName_hash1.debugName_hash1 {
+        background: black;
+      }
+      .debugName_hash1d.debugName_hash1 {
+        background: orange;
+      }
+      .debugName_hash1.debugName_hash1d.debugName_hash1 {
+        background: orange;
+      }
+      .debugName_hash1d.debugName_hash1d.debugName_hash1 {
+        background: orange;
+      }
+    `);
+  });
 });
 
 endFileScope();
diff --git a/packages/css/src/transformCss.ts b/packages/css/src/transformCss.ts
index 6b0248ee..0c11a64b 100644
--- a/packages/css/src/transformCss.ts
+++ b/packages/css/src/transformCss.ts
@@ -317,11 +317,15 @@ class Stylesheet {
       const [endIndex, [firstMatch]] = results[i];
       const startIndex = endIndex - firstMatch.length + 1;
 
-      if (startIndex >= lastReplaceIndex) {
-        // Class names can be substrings of other class names
-        // e.g. '_1g1ptzo1' and '_1g1ptzo10'
-        // If the startIndex >= lastReplaceIndex, then
-        // this is the case and this replace should be skipped
+      // Class names can be substrings of other class names
+      // e.g. '_1g1ptzo1' and '_1g1ptzo10'
+      // Additionally, concatenated classnames can be substrings of other classnames
+      // 'debugName_18fxj81' and 'debugName_18fxj81d'
+      // If this is the case then this replace should be skipped
+      const match =
+        startIndex >= lastReplaceIndex || endIndex >= lastReplaceIndex;
+
+      if (match) {
         continue;
       }