diff --git a/init.el b/init.el
index 05c7ff8..9defad9 100644
--- a/init.el
+++ b/init.el
@@ -496,10 +496,17 @@
   :ensure t
   :after transient)
 
+;; Auth Source Pass - Use pass for authentication with mail
+(use-package auth-source-pass
+  :ensure nil
+  :init
+  (auth-source-pass-enable))
+
 ;; Mu4e Mail Config
 (if (executable-find "mu")
   (use-package mu4e
     :ensure nil
+    :after auth-source-pass
     :config
     (setq mu4e-mu-binary (executable-find "mu"))
 
@@ -518,7 +525,10 @@
     (setq mu4e-compose-format-flowed t)
 
     ;; Use completing read AKA vertico
-    (setq mu4e-completing-read-function 'completing-read)
+    (setq mu4e-completing-read-function #'completing-read)
+
+    ;; Immediately send SMTP with credentials
+    (setq smtpmail-servers-requiring-authorization "*")
 
     (setq mu4e-contexts
           (list
@@ -531,9 +541,10 @@
                   (string-prefix-p "/work-cspark" (mu4e-message-field msg :maildir))))
             :vars '((user-mail-address . "work@cspark.dev")
                     (user-full-name    . "Curt Spark (Work)")
-                    (smtpmail-smtp-server  . "smtp.cspark.dev")
-                    (smtpmail-smtp-service . 465)
-                    (smtpmail-stream-type  . ssl)
+                    (smtpmail-smtp-server  . "mail.cspark.dev")
+                    (smtpmail-smtp-user  . "work@cspark.dev")
+                    (smtpmail-smtp-service . 587)
+                    (smtpmail-stream-type  . starttls)
                     (mu4e-compose-signature . "- Curt")
                     (mu4e-inbox-folder . "/work-cspark/Inbox")
                     (mu4e-drafts-folder  . "/work-cspark/Drafts")
@@ -549,9 +560,10 @@
                   (string-prefix-p "/services-cspark" (mu4e-message-field msg :maildir))))
             :vars '((user-mail-address . "services@cspark.dev")
                     (user-full-name    . "Curt Spark (services)")
-                    (smtpmail-smtp-server  . "smtp.cspark.dev")
-                    (smtpmail-smtp-service . 465)
-                    (smtpmail-stream-type  . ssl)
+                    (smtpmail-smtp-server  . "mail.cspark.dev")
+                    (smtpmail-smtp-user  . "services@cspark.dev")
+                    (smtpmail-smtp-service . 587)
+                    (smtpmail-stream-type  . starttls)
                     (mu4e-compose-signature . "- Curt")
                     (mu4e-inbox-folder . "/services-cspark/Inbox")
                     (mu4e-drafts-folder  . "/services-cspark/Drafts")
@@ -567,32 +579,72 @@
                   (string-prefix-p "/personal-cspark" (mu4e-message-field msg :maildir))))
             :vars '((user-mail-address . "personal@cspark.dev")
                     (user-full-name    . "Curt Spark (personal)")
-                    (smtpmail-smtp-server  . "smtp.cspark.dev")
-                    (smtpmail-smtp-service . 465)
-                    (smtpmail-stream-type  . ssl)
+                    (smtpmail-smtp-server  . "mail.cspark.dev")
+                    (smtpmail-smtp-user  . "personal@cspark.dev")
+                    (smtpmail-smtp-service . 587)
+                    (smtpmail-stream-type  . starttls)
                     (mu4e-compose-signature . "- Curt")
                     (mu4e-inbox-folder . "/personal-cspark/Inbox")
                     (mu4e-drafts-folder  . "/personal-cspark/Drafts")
                     (mu4e-sent-folder  . "/personal-cspark/Sent Mail")
                     (mu4e-trash-folder  . "/personal-cspark/Trash")))
 
+           ;; Alerts account
+           (make-mu4e-context
+            :name "D CSpark Alerts"
+            :match-func
+              (lambda (msg)
+                (when msg
+                  (string-prefix-p "/alerts-cspark" (mu4e-message-field msg :maildir))))
+            :vars '((user-mail-address . "alerts@cspark.dev")
+                    (user-full-name    . "Curt Spark (alerts)")
+                    (smtpmail-smtp-server  . "mail.cspark.dev")
+                    (smtpmail-smtp-user  . "alerts@cspark.dev")
+                    (smtpmail-smtp-service . 587)
+                    (smtpmail-stream-type  . starttls)
+                    (mu4e-compose-signature . "- Curt")
+                    (mu4e-inbox-folder . "/alerts-cspark/Inbox")
+                    (mu4e-drafts-folder  . "/alerts-cspark/Drafts")
+                    (mu4e-sent-folder  . "/alerts-cspark/Sent Mail")
+                    (mu4e-trash-folder  . "/alerts-cspark/Trash")))
+
            ;; Tuxtank Services account
            (make-mu4e-context
-            :name "D Tuxtank Services"
+            :name "E Tuxtank Services"
             :match-func
               (lambda (msg)
                 (when msg
                   (string-prefix-p "/personal-tuxtank" (mu4e-message-field msg :maildir))))
             :vars '((user-mail-address . "personal@tuxtank.dev")
                     (user-full-name    . "Tuxtank (personal)")
-                    (smtpmail-smtp-server  . "smtp.tuxtank.dev")
-                    (smtpmail-smtp-service . 465)
-                    (smtpmail-stream-type  . ssl)
+                    (smtpmail-smtp-server  . "mail.tuxtank.dev")
+                    (smtpmail-smtp-user  . "personal@tuxtank.dev")
+                    (smtpmail-smtp-service . 587)
+                    (smtpmail-stream-type  . starttls)
                     (mu4e-compose-signature . "- Tuxtank")
                     (mu4e-inbox-folder . "/personal-tuxtank/Inbox")
                     (mu4e-drafts-folder  . "/personal-tuxtank/Drafts")
                     (mu4e-sent-folder  . "/personal-tuxtank/Sent Mail")
-                    (mu4e-trash-folder  . "/personal-tuxtank/Trash")))))))
+                    (mu4e-trash-folder  . "/personal-tuxtank/Trash")))
+
+           ;; Tuxtank Alerts account
+           (make-mu4e-context
+            :name "F Tuxtank Alerts"
+            :match-func
+              (lambda (msg)
+                (when msg
+                  (string-prefix-p "/alerts-tuxtank" (mu4e-message-field msg :maildir))))
+            :vars '((user-mail-address . "alerts@tuxtank.dev")
+                    (user-full-name    . "Tuxtank (alerts)")
+                    (smtpmail-smtp-server  . "mail.tuxtank.dev")
+                    (smtpmail-smtp-user  . "alerts@tuxtank.dev")
+                    (smtpmail-smtp-service . 587)
+                    (smtpmail-stream-type  . starttls)
+                    (mu4e-compose-signature . "- Tuxtank")
+                    (mu4e-inbox-folder . "/alerts-tuxtank/Inbox")
+                    (mu4e-drafts-folder  . "/alerts-tuxtank/Drafts")
+                    (mu4e-sent-folder  . "/alerts-tuxtank/Sent Mail")
+                    (mu4e-trash-folder  . "/alerts-tuxtank/Trash")))))))
 
 
     ;(setq mu4e-maildir-shortcuts