diff --git a/CHANGELOG.md b/CHANGELOG.md
index 5ffd1b7b3e6d..12242417ebbc 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -24,6 +24,12 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
 
 - Fix defining colors as functions when color opacity plugins are disabled ([#5470](https://github.com/tailwindlabs/tailwindcss/pull/5470))
 
+## [2.2.17] - 2021-10-13
+
+### Fixed
+
+- Configure chokidar's `awaitWriteFinish` setting to avoid occasional stale builds on Windows ([#5758](https://github.com/tailwindlabs/tailwindcss/pull/5758))
+
 ## [2.2.16] - 2021-09-26
 
 ### Fixed
@@ -1582,7 +1588,8 @@ No release notes
 
 - Everything!
 
-[unreleased]: https://github.com/tailwindlabs/tailwindcss/compare/v2.2.16...HEAD
+[unreleased]: https://github.com/tailwindlabs/tailwindcss/compare/v2.2.17...HEAD
+[2.2.16]: https://github.com/tailwindlabs/tailwindcss/compare/v2.2.16...v2.2.17
 [2.2.16]: https://github.com/tailwindlabs/tailwindcss/compare/v2.2.15...v2.2.16
 [2.2.15]: https://github.com/tailwindlabs/tailwindcss/compare/v2.2.14...v2.2.15
 [2.2.14]: https://github.com/tailwindlabs/tailwindcss/compare/v2.2.13...v2.2.14
diff --git a/package-lock.json b/package-lock.json
index ed9635bc897c..aab9baab1871 100644
--- a/package-lock.json
+++ b/package-lock.json
@@ -1,11 +1,11 @@
 {
   "name": "tailwindcss",
-  "version": "2.2.16",
+  "version": "2.2.17",
   "lockfileVersion": 2,
   "requires": true,
   "packages": {
     "": {
-      "version": "2.2.16",
+      "version": "2.2.17",
       "license": "MIT",
       "dependencies": {
         "arg": "^5.0.1",
diff --git a/package.json b/package.json
index 88432c6bdab3..5060b4751571 100644
--- a/package.json
+++ b/package.json
@@ -1,6 +1,6 @@
 {
   "name": "tailwindcss",
-  "version": "2.2.16",
+  "version": "2.2.17",
   "description": "A utility-first CSS framework for rapidly building custom user interfaces.",
   "license": "MIT",
   "main": "lib/index.js",
diff --git a/src/cli.js b/src/cli.js
index 0c05a30d6e09..34e116e212e1 100644
--- a/src/cli.js
+++ b/src/cli.js
@@ -734,6 +734,13 @@ async function build() {
 
     watcher = chokidar.watch([...contextDependencies, ...extractFileGlobs(config)], {
       ignoreInitial: true,
+      awaitWriteFinish:
+        process.platform === 'win32'
+          ? {
+              stabilityThreshold: 50,
+              pollInterval: 10,
+            }
+          : false,
     })
 
     let chain = Promise.resolve()
diff --git a/src/jit/lib/setupWatchingContext.js b/src/jit/lib/setupWatchingContext.js
index edbf5fba5e6f..0b20f8bd6d34 100644
--- a/src/jit/lib/setupWatchingContext.js
+++ b/src/jit/lib/setupWatchingContext.js
@@ -84,6 +84,13 @@ function rebootWatcher(context, configPath, configDependencies, candidateFiles)
 
     watcher = chokidar.watch([...candidateFiles, ...configDependencies], {
       ignoreInitial: true,
+      awaitWriteFinish:
+        process.platform === 'win32'
+          ? {
+              stabilityThreshold: 50,
+              pollInterval: 10,
+            }
+          : false,
     })
 
     setWatcher(context, watcher)