diff --git a/packages/babel-plugin-transform-typescript/src/index.js b/packages/babel-plugin-transform-typescript/src/index.js
index cc6c1be62f..db0104f5e9 100644
--- a/packages/babel-plugin-transform-typescript/src/index.js
+++ b/packages/babel-plugin-transform-typescript/src/index.js
@@ -250,7 +250,11 @@ export default declare((api, { jsxPragma = "React" }) => {
       },
 
       TSAsExpression(path) {
-        path.replaceWith(path.node.expression);
+        let { node } = path;
+        do {
+          node = node.expression;
+        } while (t.isTSAsExpression(node));
+        path.replaceWith(node);
       },
 
       TSNonNullExpression(path) {
diff --git a/packages/babel-plugin-transform-typescript/test/fixtures/cast/multiple-assert-and-assign/input.js b/packages/babel-plugin-transform-typescript/test/fixtures/cast/multiple-assert-and-assign/input.js
new file mode 100644
index 0000000000..c35da37ddf
--- /dev/null
+++ b/packages/babel-plugin-transform-typescript/test/fixtures/cast/multiple-assert-and-assign/input.js
@@ -0,0 +1 @@
+(a as number as any) = 42;
\ No newline at end of file
diff --git a/packages/babel-plugin-transform-typescript/test/fixtures/cast/multiple-assert-and-assign/output.js b/packages/babel-plugin-transform-typescript/test/fixtures/cast/multiple-assert-and-assign/output.js
new file mode 100644
index 0000000000..e095ff18d1
--- /dev/null
+++ b/packages/babel-plugin-transform-typescript/test/fixtures/cast/multiple-assert-and-assign/output.js
@@ -0,0 +1 @@
+a = 42;