diff --git a/CHANGELOG.md b/CHANGELOG.md
index 5f5bd398bda8..9a8efd6b0158 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
 
 - Fix missing `supports` in types ([#9616](https://github.com/tailwindlabs/tailwindcss/pull/9616))
+- Fix missing PostCSS dependencies in the CLI ([#9617](https://github.com/tailwindlabs/tailwindcss/pull/9617))
 
 ## [3.2.0] - 2022-10-19
 
diff --git a/integrations/tailwindcss-cli/tests/cli.test.js b/integrations/tailwindcss-cli/tests/cli.test.js
index 41ff2de4ebab..b43f2975aa1f 100644
--- a/integrations/tailwindcss-cli/tests/cli.test.js
+++ b/integrations/tailwindcss-cli/tests/cli.test.js
@@ -411,6 +411,31 @@ describe('Build command', () => {
       `
     )
 
+    await writeInputFile(
+      'imported.css',
+      css`
+        @layer utilities {
+          .something-cool {
+            color: blue;
+          }
+        }
+      `
+    )
+
+    await runningProcess.onStderr(function ready(message) {
+      return message.includes('Done in')
+    })
+
+    expect(await readOutputFile('main.css')).toIncludeCss(
+      css`
+        @media (min-width: 768px) {
+          .md\:something-cool {
+            color: blue;
+          }
+        }
+      `
+    )
+
     return runningProcess.stop()
   })
 
diff --git a/integrations/tailwindcss-cli/tests/integration.test.js b/integrations/tailwindcss-cli/tests/integration.test.js
index fbfdc6f0db96..4a76cdfeff26 100644
--- a/integrations/tailwindcss-cli/tests/integration.test.js
+++ b/integrations/tailwindcss-cli/tests/integration.test.js
@@ -605,4 +605,105 @@ describe('watcher', () => {
 
     return runningProcess.stop()
   })
+
+  test('classes are generated (and kept) when the index.html file changes (and removed when css/config files are changed)', async () => {
+    let runningProcess = $('node ../../lib/cli.js -i ./src/index.css -o ./dist/main.css -w')
+
+    // Start with a simple single class
+    await writeInputFile('index.html', html`<div class="font-bold"></div>`)
+    await runningProcess.onStderr(ready)
+    expect(await readOutputFile('main.css')).toIncludeCss(
+      css`
+        .font-bold {
+          font-weight: 700;
+        }
+      `
+    )
+
+    // Add another class
+    await writeInputFile('index.html', html`<div class="flex font-bold"></div>`)
+    await runningProcess.onStderr(ready)
+    expect(await readOutputFile('main.css')).toIncludeCss(
+      css`
+        .flex {
+          display: flex;
+        }
+
+        .font-bold {
+          font-weight: 700;
+        }
+      `
+    )
+
+    // Remove a class, because of performance reasons both classes will still be in the css file
+    await writeInputFile('index.html', html`<div class="font-bold"></div>`)
+    await runningProcess.onStderr(ready)
+    expect(await readOutputFile('main.css')).toIncludeCss(
+      css`
+        .flex {
+          display: flex;
+        }
+
+        .font-bold {
+          font-weight: 700;
+        }
+      `
+    )
+
+    // Save the index.css file, this should trigger a fresh context
+    await writeInputFile(
+      'index.css',
+      css`
+        @tailwind base;
+        @tailwind components;
+        @tailwind utilities;
+      `
+    )
+    await runningProcess.onStderr(ready)
+
+    // Only 1 class should stay, because we started from scratch
+    expect(await readOutputFile('main.css')).toIncludeCss(
+      css`
+        .font-bold {
+          font-weight: 700;
+        }
+      `
+    )
+
+    // Add another class
+    await writeInputFile('index.html', html`<div class="flex font-bold"></div>`)
+    await runningProcess.onStderr(ready)
+    expect(await readOutputFile('main.css')).toIncludeCss(
+      css`
+        .flex {
+          display: flex;
+        }
+
+        .font-bold {
+          font-weight: 700;
+        }
+      `
+    )
+
+    // Remove a class, because of performance reasons both classes will still be in the css file
+    await writeInputFile('index.html', html`<div class="font-bold"></div>`)
+    await runningProcess.onStderr(ready)
+
+    // If everything goes right, then both classes should still be here (because of the performance
+    // improvement). If we didn't solve the bug where from now on every save is a fresh context
+    // then this only has 1 class. So let's hope there are 2!
+    expect(await readOutputFile('main.css')).toIncludeCss(
+      css`
+        .flex {
+          display: flex;
+        }
+
+        .font-bold {
+          font-weight: 700;
+        }
+      `
+    )
+
+    return runningProcess.stop()
+  })
 })
diff --git a/src/cli/build/plugin.js b/src/cli/build/plugin.js
index 51177db79113..a06bca3be1ae 100644
--- a/src/cli/build/plugin.js
+++ b/src/cli/build/plugin.js
@@ -328,6 +328,26 @@ export async function createProcessor(args, cliConfigPath) {
 
     return readInput()
       .then((css) => processor.process(css, { ...postcssOptions, from: input, to: output }))
+      .then((result) => {
+        if (!state.watcher) {
+          return result
+        }
+
+        env.DEBUG && console.time('Recording PostCSS dependencies')
+        for (let message of result.messages) {
+          if (message.type === 'dependency') {
+            state.contextDependencies.add(message.file)
+          }
+        }
+        env.DEBUG && console.timeEnd('Recording PostCSS dependencies')
+
+        // TODO: This needs to be in a different spot
+        env.DEBUG && console.time('Watch new files')
+        state.watcher.refreshWatchedFiles()
+        env.DEBUG && console.timeEnd('Watch new files')
+
+        return result
+      })
       .then((result) => {
         if (!output) {
           process.stdout.write(result.css)
diff --git a/src/cli/build/watching.js b/src/cli/build/watching.js
index 8ebceccf5cc7..9b5462a244fd 100644
--- a/src/cli/build/watching.js
+++ b/src/cli/build/watching.js
@@ -62,7 +62,7 @@ export function createWatcher(args, { state, rebuild }) {
       extension: path.extname(file).slice(1),
     })
 
-    chain = chain.then(() => rebuild(changedContent))
+    chain = chain.then(() => rebuild(changedContent.splice(0)))
 
     return chain
   }