diff --git a/README.md b/README.md
index 031725bc..e6608881 100644
--- a/README.md
+++ b/README.md
@@ -23,10 +23,6 @@ curl -s https://raw.githubusercontent.com/animenotifier/notify.moe/go/install.sh
 * In your browser, import the file `security/default/root.crt` as a trusted Root authority
 * Open `https://beta.notify.moe`
 
-## OS restarts
-
-* If you restart your operating system, run `make ports` to update your port bindings
-
 ## Author
 
 | [![Eduard Urbach on Twitter](https://gravatar.com/avatar/16ed4d41a5f244d1b10de1b791657989?s=70)](https://twitter.com/eduardurbach "Follow @eduardurbach on Twitter") |
diff --git a/main.go b/main.go
index c2445532..d08f7686 100644
--- a/main.go
+++ b/main.go
@@ -49,9 +49,12 @@ func configure(app *aero.Application) *aero.Application {
 	// API
 	arn.API.Install(app)
 
-	// Domain
+	// Development server configuration
 	if arn.IsDevelopment() {
 		app.Config.Domain = "beta.notify.moe"
+
+		// Test connectivity
+		app.OnStart(testConnectivity)
 	}
 
 	// Authentication
diff --git a/ports.go b/ports.go
new file mode 100644
index 00000000..2641db9c
--- /dev/null
+++ b/ports.go
@@ -0,0 +1,33 @@
+package main
+
+import (
+	"crypto/tls"
+	"fmt"
+	"os"
+	"os/exec"
+
+	"github.com/fatih/color"
+)
+
+// testConnectivity will test if port 443 is accessible or not.
+// If not, it will attempt to run "sudo make ports" and consume
+// execution once the user has entered the password.
+func testConnectivity() {
+	config := tls.Config{
+		InsecureSkipVerify: true,
+	}
+
+	_, err := tls.Dial("tcp", ":443", &config)
+
+	if err != nil {
+		fmt.Println("--------------------------------------------------------------------------------")
+		color.Red("HTTPS port 443 is not accessible")
+		fmt.Println("Running", color.YellowString("make ports"), "to be able to access", color.GreenString("https://"+app.Config.Domain))
+
+		cmd := exec.Command("sudo", "make", "ports")
+		cmd.Stdout = os.Stdout
+		cmd.Stderr = os.Stderr
+		cmd.Stdin = os.Stdin
+		cmd.Run()
+	}
+}