diff --git a/CHANGELOG.md b/CHANGELOG.md
index 3ddecbb34ff9..d6ef24b4883a 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -10,6 +10,7 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
 ### Fixed
 
 - Fixed use of `raw` content in the CLI ([#9773](https://github.com/tailwindlabs/tailwindcss/pull/9773))
+- Pick up changes from files that are both context and content deps ([#9787](https://github.com/tailwindlabs/tailwindcss/pull/9787))
 
 ## [3.2.2] - 2022-11-04
 
diff --git a/src/lib/content.js b/src/lib/content.js
index c486a6886374..0f89913d27f7 100644
--- a/src/lib/content.js
+++ b/src/lib/content.js
@@ -196,7 +196,14 @@ function resolveChangedFiles(candidateFiles, fileModifiedMap) {
     let prevModified = fileModifiedMap.has(file) ? fileModifiedMap.get(file) : -Infinity
     let modified = fs.statSync(file).mtimeMs
 
-    if (modified > prevModified) {
+    // This check is intentionally >= because we track the last modified time of context dependencies
+    // earier in the process and we want to make sure we don't miss any changes that happen
+    // when a context dependency is also a content dependency
+    // Ideally, we'd do all this tracking at one time but that is a larger refactor
+    // than we want to commit to right now, so this is a decent compromise.
+    // This should be sufficient because file modification times will be off by at least
+    // 1ms (the precision of fstat in Node) in most cases if they exist and were changed.
+    if (modified >= prevModified) {
       changedFiles.add(file)
       fileModifiedMap.set(file, modified)
     }