diff --git a/changelog.md b/changelog.md
index f19522168..33fb80e20 100755
--- a/changelog.md
+++ b/changelog.md
@@ -8,6 +8,8 @@ Since you are interested in what happens next, in case, you work for a for-profi
 
 - [all] Flow types are now moved from .js files to .flow type defs [1509](https://github.com/cssinjs/jss/pull/1509)
 
+- [all] Upgrade typescript to 4.4.2 [1550](https://github.com/cssinjs/jss/pull/1550)
+
 ## 10.7.1 (2021-6-28)
 
 ### Bug fixes
diff --git a/package.json b/package.json
index 54dd049f4..508be5aff 100644
--- a/package.json
+++ b/package.json
@@ -98,7 +98,7 @@
     "rollup-plugin-terser": "^7.0.2",
     "shelljs": "^0.8.2",
     "sinon": "4.5.0",
-    "typescript": "^3.7.0",
+    "typescript": "^4.4.2",
     "webpack": "^4.28.3",
     "zen-observable": "^0.6.0"
   }
diff --git a/packages/react-jss/tests/types/withStyles.tsx b/packages/react-jss/tests/types/withStyles.tsx
index b7dfa9aa1..4838e6df5 100644
--- a/packages/react-jss/tests/types/withStyles.tsx
+++ b/packages/react-jss/tests/types/withStyles.tsx
@@ -136,8 +136,7 @@ ComponentTest = () => <ResultingComponent property="" />
 
 /* -------------------- Failing Cases -------------------- */
 
-// A function argument cannot provide another defined theme type conflicting with `undefined`
-function failingFunctionRedefineTheme(theme: MyTheme): Styles<string, unknown, any> {
+function failingFunctionWrongTheme(theme: MyTheme): Styles<string, unknown, MyTheme> {
   return {
     someClassName: '',
     anotherClassName: {
@@ -146,7 +145,7 @@ function failingFunctionRedefineTheme(theme: MyTheme): Styles<string, unknown, a
   }
 }
 
-function passingFunctionUnknownTheme(theme: MyTheme): Styles<string, unknown, unknown> {
+function failingFunctionNullTheme(theme: MyTheme): Styles<string, unknown, null> {
   return {
     someClassName: '',
     anotherClassName: {
@@ -155,16 +154,7 @@ function passingFunctionUnknownTheme(theme: MyTheme): Styles<string, unknown, un
   }
 }
 
-function passingFunctionNullTheme(theme: MyTheme): Styles<string, unknown, null> {
-  return {
-    someClassName: '',
-    anotherClassName: {
-      fontWeight: 'bold'
-    }
-  }
-}
-
-// @ts-expect-error
-withStyles(failingFunctionRedefineTheme)(SimpleComponent)
-withStyles(passingFunctionUnknownTheme)(SimpleComponent)
-withStyles(passingFunctionNullTheme)(SimpleComponent)
+// @ts-expect-error - can't override `theme` argument
+withStyles(failingFunctionWrongTheme)(SimpleComponent)
+// @ts-expect-error - can't use null as a theme
+withStyles(failingFunctionNullTheme)(SimpleComponent)
diff --git a/yarn.lock b/yarn.lock
index eed488c5d..2e35607bf 100644
--- a/yarn.lock
+++ b/yarn.lock
@@ -10000,10 +10000,10 @@ typedarray@^0.0.6:
   resolved "https://registry.yarnpkg.com/typedarray/-/typedarray-0.0.6.tgz#867ac74e3864187b1d3d47d996a78ec5c8830777"
   integrity sha1-hnrHTjhkGHsdPUfZlqeOxciDB3c=
 
-typescript@^3.7.0:
-  version "3.9.3"
-  resolved "https://registry.yarnpkg.com/typescript/-/typescript-3.9.3.tgz#d3ac8883a97c26139e42df5e93eeece33d610b8a"
-  integrity sha512-D/wqnB2xzNFIcoBG9FG8cXRDjiqSTbG2wd8DMZeQyJlP1vfTkIxH4GKveWaEBYySKIg+USu+E+EDIR47SqnaMQ==
+typescript@^4.4.2:
+  version "4.4.2"
+  resolved "https://registry.yarnpkg.com/typescript/-/typescript-4.4.2.tgz#6d618640d430e3569a1dfb44f7d7e600ced3ee86"
+  integrity sha512-gzP+t5W4hdy4c+68bfcv0t400HVJMMd2+H9B7gae1nQlBzCqvrXX+6GL/b3GAgyTH966pzrZ70/fRjwAtZksSQ==
 
 uglify-js@^3.1.4:
   version "3.8.0"