diff --git a/directory.go b/directory.go
index ec2f3e4..9413692 100644
--- a/directory.go
+++ b/directory.go
@@ -17,6 +17,9 @@ func Login(username string, password string) error {
 	request, _ := http.NewRequest("GET", directoryPageUrl.String(), nil)
 	ApplyUtsaHeaders(request)
 	response, err := DoRequestNoRead(request)
+	if err != nil {
+		return nil
+	}
 
 	// Verify that we were redirected to the login page
 	if response.StatusCode != 302 {
@@ -100,11 +103,18 @@ func Login(username string, password string) error {
 	}
 
 	// Request the redirect page
-	request, _ = http.NewRequest("GET", fmt.Sprintf("%s%s", "https://www.utsa.edu", response.Header.Get("Location")), nil)
+	redirectUrl := fmt.Sprintf("%s%s", "https://www.utsa.edu", response.Header.Get("Location"))
+	request, _ = http.NewRequest("GET", redirectUrl, nil)
 	ApplyUtsaHeaders(request)
-	response, body, err = DoRequest(request)
+	response, err = DoRequestNoRead(request)
+	if err != nil {
+		return err
+	} else if response.StatusCode != 200 {
+		return fmt.Errorf("non-200 status after login attempt")
+	}
 
-	doc, err = goquery.NewDocumentFromReader(strings.NewReader(string(body)))
+	// Parse the response body
+	doc, err = goquery.NewDocumentFromReader(response.Body)
 	if err != nil {
 		return fmt.Errorf("error parsing response body")
 	}
@@ -136,9 +146,49 @@ func Login(username string, password string) error {
 }
 
 func CheckLoggedIn() (bool, error) {
+	// Check if required cookie exists
+	utsaUrl, _ := url.Parse("https://www.utsa.edu")
+	cookies := client.Jar.Cookies(utsaUrl)
+	_, authCookieFound := lo.Find(cookies, func(cookie *http.Cookie) bool {
+		return strings.Contains(cookie.Name, ".ADAuthCookie")
+	})
+
+	if !authCookieFound {
+		log.Debug().Int("count", len(cookies)).Msg("ActiveDirectory Auth Cookie Not Found")
+		return false, nil
+	}
+
+	// Send a authenticated-only request
 	directoryPageUrl, _ := url.Parse("https://www.utsa.edu/directory/AdvancedSearch")
 	request, _ := http.NewRequest("GET", directoryPageUrl.String(), nil)
 	ApplyUtsaHeaders(request)
+	response, err := DoRequestNoRead(request)
+	if err != nil {
+		return false, fmt.Errorf("could not send redirect check request")
+	}
+
+	// If it's not a 302
+	if response.StatusCode != 302 {
+		// No planning for non-200 responses (this will blow up one day, probably a 400 or 500)
+		if response.StatusCode != 200 {
+			log.Fatal().Int("code", response.StatusCode).Msg("Unexpected Login Check Response Code")
+		}
+
+		// Parse the response document
+		doc, err := goquery.NewDocumentFromReader(response.Body)
+		if err != nil {
+			return false, fmt.Errorf("error parsing response body")
+		}
+
+		// Try to find the log out button
+		logOffFound := false
+		doc.Find("a.dropdown-item").Each(func(i int, s *goquery.Selection) {
+			if !logOffFound && strings.Contains(s.Text(), "Log Off") {
+				log.Debug().Int("index", i).Msg("Log Off Element Found")
+				logOffFound = true
+			}
+		})
+	}
 
 	return false, nil
 }
diff --git a/main.go b/main.go
index e0cdf7d..c6bc0b0 100644
--- a/main.go
+++ b/main.go
@@ -15,8 +15,10 @@ import (
 	"github.com/samber/lo"
 )
 
-var client *http.Client
-var db *badger.DB
+var (
+	client *http.Client
+	db     *badger.DB
+)
 
 func init() {
 	log.Logger = zerolog.New(logSplitter{}).With().Timestamp().Logger()
@@ -55,7 +57,6 @@ func SaveCookies() {
 	// Marshal cookies, create transaction
 	marshalledCookies, _ := json.Marshal(utsaCookies)
 	err := db.Update(func(txn *badger.Txn) error {
-		log.Printf(string(marshalledCookies))
 		err := txn.Set([]byte("utsa_cookies"), []byte(marshalledCookies))
 		return err
 	})
@@ -87,6 +88,7 @@ func LoadCookies() {
 		log.Err(err).Msg("Failed to load marshalled cookies")
 	}
 
+	// Place cookies in the jar
 	utsaUrl, _ := url.Parse("https://www.utsa.edu")
 	client.Jar.SetCookies(utsaUrl, lo.Map(cookies, func(cookie http.Cookie, _ int) *http.Cookie {
 		return &cookie
@@ -104,9 +106,17 @@ func main() {
 	username := os.Getenv("UTSA_USERNAME")
 	password := os.Getenv("UTSA_PASSWORD")
 
-	err := Login(username, password)
+	loggedIn, err := CheckLoggedIn()
 	if err != nil {
-		log.Fatal().Err(err).Msg("Failed to login")
+		log.Fatal().Err(err).Msg("Failed to check login state")
+	}
+
+	if !loggedIn {
+		log.Debug().Str("username", username).Msg("Attempting Login")
+		err := Login(username, password)
+		if err != nil {
+			log.Fatal().Err(err).Msg("Failed to login")
+		}
 	}
 
 	defer db.Close()