diff --git a/Package.resolved b/Package.resolved
index d3d55a8b..1b211b58 100644
--- a/Package.resolved
+++ b/Package.resolved
@@ -28,6 +28,15 @@
           "version": "4.2.0"
         }
       },
+      {
+        "package": "FileWatcher",
+        "repositoryURL": "https://github.com/eonist/FileWatcher.git",
+        "state": {
+          "branch": null,
+          "revision": "e67c2a99502eade343fecabeca8c57e749a55b59",
+          "version": "0.2.3"
+        }
+      },
       {
         "package": "Ink",
         "repositoryURL": "https://github.com/johnsundell/ink.git",
diff --git a/Package.swift b/Package.swift
index f81064cc..e6df55e1 100644
--- a/Package.swift
+++ b/Package.swift
@@ -50,7 +50,13 @@ let package = Package(
             name: "CollectionConcurrencyKit",
             url: "https://github.com/johnsundell/collectionConcurrencyKit.git",
             from: "0.1.0"
+        ),
+        .package(
+            name: "FileWatcher",
+            url: "https://github.com/eonist/FileWatcher.git",
+            from: "0.2.3"
         )
+
     ],
     targets: [
         .target(
@@ -66,7 +72,7 @@ let package = Package(
         ),
         .target(
             name: "PublishCLICore",
-            dependencies: ["Publish"]
+            dependencies: ["Publish", .byName(name: "FileWatcher", condition: .when(platforms: [.macOS]))]
         ),
         .testTarget(
             name: "PublishTests",
diff --git a/Sources/PublishCLICore/CLI.swift b/Sources/PublishCLICore/CLI.swift
index 128bdf26..7cd6b522 100644
--- a/Sources/PublishCLICore/CLI.swift
+++ b/Sources/PublishCLICore/CLI.swift
@@ -9,6 +9,7 @@ import Foundation
 import ShellOut
 
 public struct CLI {
+    private static let defaultPortNumber = 8000
     private let arguments: [String]
     private let publishRepositoryURL: URL
     private let publishVersion: String
@@ -44,7 +45,8 @@ public struct CLI {
             try deployer.deploy()
         case "run":
             let portNumber = extractPortNumber(from: arguments)
-            let runner = WebsiteRunner(folder: folder, portNumber: portNumber)
+            let shouldWatch = extractShouldWatch(from: arguments)
+            let runner = WebsiteRunner(folder: folder, portNumber: portNumber, shouldWatch: shouldWatch)
             try runner.run()
         default:
             outputHelpText()
@@ -68,24 +70,30 @@ private extension CLI {
         - run: Generate and run a localhost server on default port 8000
                for the website in the current folder. Use the "-p"
                or "--port" option for customizing the default port.
+               Use the "-w" or "--watch" option to watch for file changes.
         - deploy: Generate and deploy the website in the current
                folder, according to its deployment method.
         """)
     }
 
     private func extractPortNumber(from arguments: [String]) -> Int {
-        if arguments.count > 3 {
-            switch arguments[2] {
-            case "-p", "--port":
-                guard let portNumber = Int(arguments[3]) else {
-                    break
-                }
-                return portNumber
-            default:
-                return 8000 // default portNumber
-            }
+        guard let index = arguments.firstIndex(of: "-p") ?? arguments.firstIndex(of: "--port") else {
+            return Self.defaultPortNumber
         }
-        return 8000 // default portNumber
+
+        guard arguments.count > index + 1 else {
+            return Self.defaultPortNumber
+        }
+
+        guard let portNumber = Int(arguments[index + 1]) else {
+            return Self.defaultPortNumber
+        }
+
+        return portNumber
+    }
+
+    private func extractShouldWatch(from arguments: [String]) -> Bool {
+        arguments.contains("-w") || arguments.contains("--watch")
     }
 
     private func resolveProjectKind(from arguments: [String]) -> ProjectKind {
diff --git a/Sources/PublishCLICore/WebsiteRunner.swift b/Sources/PublishCLICore/WebsiteRunner.swift
index 326a235c..6a0563ec 100644
--- a/Sources/PublishCLICore/WebsiteRunner.swift
+++ b/Sources/PublishCLICore/WebsiteRunner.swift
@@ -1,20 +1,88 @@
 /**
-*  Publish
-*  Copyright (c) John Sundell 2019
-*  MIT license, see LICENSE file for details
-*/
+ *  Publish
+ *  Copyright (c) John Sundell 2019
+ *  MIT license, see LICENSE file for details
+ */
 
 import Foundation
 import Files
 import ShellOut
 
+#if canImport(FileWatcher)
+import FileWatcher
+#endif
+
 internal struct WebsiteRunner {
+    static let nanosecondsPerSecond: UInt64 = 1_000_000_000
+    static let normalTerminationStatus = 15
+    static let debounceDuration = 3 * nanosecondsPerSecond
+    static let runLoopInterval: TimeInterval = 0.1
+    static let exitMessage = "Press CTRL+C to stop the server and exit"
     let folder: Folder
-    var portNumber: Int
+    let portNumber: Int
+    let shouldWatch: Bool
+
+    var foldersToWatch: [Folder] {
+        get throws {
+            try ["Sources", "Resources", "Content"].map(folder.subfolder(named:))
+        }
+    }
 
     func run() throws {
+        let serverProcess: Process = try generateAndRun()
+        let watchTask = shouldWatch ? watch() : nil
+
+        let interruptHandler = registerInterruptHandler {
+            watchTask?.cancel()
+            serverProcess.terminate()
+            exit(0)
+        }
+
+        interruptHandler.resume()
+
+        while true {
+            RunLoop.main.run(until: Date(timeIntervalSinceNow: Self.runLoopInterval))
+        }
+    }
+}
+
+private extension WebsiteRunner {
+    func registerInterruptHandler(_ handler: @escaping () -> Void) -> DispatchSourceSignal {
+        let interruptHandler = DispatchSource.makeSignalSource(signal: SIGINT, queue: .main)
+
+        signal(SIGINT, SIG_IGN)
+
+        interruptHandler.setEventHandler(handler: handler)
+        return interruptHandler
+    }
+
+    func watch() -> Task<Void, Error>? {
+#if canImport(FileWatcher)
+        return Task.detached {
+            for try await _ in FileWatcher.changes(on: try foldersToWatch, debouncedBy: Self.debounceDuration) {
+                print("Changes detected, regenerating...")
+                let generator = WebsiteGenerator(folder: folder)
+                do {
+                    try generator.generate()
+                    print(Self.exitMessage)
+                } catch {
+                    outputErrorMessage("Regeneration failed")
+                }
+            }
+        }
+#else
+        print("File watching not available")
+        return nil
+#endif
+    }
+
+    func generate() throws {
         let generator = WebsiteGenerator(folder: folder)
         try generator.generate()
+    }
+
+    func generateAndRun() throws -> Process {
+        try generate()
 
         let outputFolder = try resolveOutputFolder()
 
@@ -24,7 +92,7 @@ internal struct WebsiteRunner {
         print("""
         🌍 Starting web server at http://localhost:\(portNumber)
 
-        Press ENTER to stop the server and exit
+        \(Self.exitMessage)
         """)
 
         serverQueue.async {
@@ -44,12 +112,9 @@ internal struct WebsiteRunner {
             exit(1)
         }
 
-        _ = readLine()
-        serverProcess.terminate()
+        return serverProcess
     }
-}
 
-private extension WebsiteRunner {
     func resolveOutputFolder() throws -> Folder {
         do { return try folder.subfolder(named: "Output") }
         catch { throw CLIError.outputFolderNotFound }
@@ -70,6 +135,60 @@ private extension WebsiteRunner {
             """
         }
 
-        fputs("\n❌ Failed to start local web server:\n\(message)\n", stderr)
+        outputErrorMessage("Failed to start local web server:\n\(message)")
+    }
+
+    func outputErrorMessage(_ message: String) {
+        fputs("\n❌ \(message)\n", stderr)
+    }
+}
+
+#if canImport(FileWatcher)
+private extension FileWatcher {
+    static func changes(on folders: [Folder], debouncedBy nanoseconds: UInt64?) -> AsyncThrowingStream<String, Error> {
+        .init { continuation in
+            let watcher = FileWatcher(folders.map(\.path))
+
+            var deferredTask: Task<Void, Error>?
+
+            watcher.callback = { event in
+                guard event.isFileChanged || event.isDirectoryChanged else {
+                    return
+                }
+
+                guard let nanoseconds = nanoseconds else {
+                    continuation.yield(event.path)
+                    return
+                }
+
+                deferredTask?.cancel()
+
+                deferredTask = Task {
+                    do {
+                        try await Task.sleep(nanoseconds: nanoseconds)
+                        continuation.yield(event.path)
+                    } catch where !(error is CancellationError) {
+                        continuation.finish()
+                    }
+                }
+            }
+
+            watcher.start()
+
+            continuation.onTermination = { _ in
+                watcher.stop()
+            }
+        }
+    }
+}
+
+private extension FileWatcherEvent {
+    var isFileChanged: Bool {
+        fileRenamed || fileRemoved || fileCreated || fileModified
+    }
+
+    var isDirectoryChanged: Bool {
+        dirRenamed || dirRemoved || dirCreated || dirModified
     }
 }
+#endif