diff --git a/static/css/main.css b/static/css/main.css
index 64c02f39..a8379a60 100644
--- a/static/css/main.css
+++ b/static/css/main.css
@@ -448,3 +448,6 @@ table.dataTable thead .sorting_desc:after {
 .timeline-event-table{
 	display:none;
 }
+.tooltip-inner {
+	width:300px !important;
+}
diff --git a/templates/campaigns.html b/templates/campaigns.html
index e1c807f2..4075ed79 100644
--- a/templates/campaigns.html
+++ b/templates/campaigns.html
@@ -96,7 +96,10 @@
                           <br />
                           <label class="control-label" for="smtp_server">Password:</label>
                           <input type="password" class="form-control" placeholder="Password" value="" name="password">
-                          <br />
+			  <div class="checkbox checkbox-primary">
+                		<input id="ignore_cert_errors" type="checkbox" checked>
+				<label for="ignore_cert_errors">Ignore Certificate Errors <i class="fa fa-question-circle" data-toggle="tooltip" data-placement="right" title="Ignore common certificate errors such as self-signed certs (exposes you to MiTM attacks - use carefully!)"></i></label>
+            		  </div>
 			  <button type="button" data-toggle="modal" data-target="#sendTestEmailModal" class="btn btn-primary"><i class="fa fa-envelope"></i> Send Test Email</button>
                       </div>
                  </div>
diff --git a/worker/worker.go b/worker/worker.go
index 0044753b..cdefe333 100644
--- a/worker/worker.go
+++ b/worker/worker.go
@@ -2,8 +2,10 @@ package worker
 
 import (
 	"bytes"
+	"crypto/tls"
 	"errors"
 	"log"
+	"net"
 	"net/mail"
 	"net/smtp"
 	"os"
@@ -198,3 +200,87 @@ func SendTestEmail(s *models.SendTestEmailRequest) error {
 	}
 	return err
 }
+
+// sendEmail is a copy of the net/smtp#SendMail function
+// that has the option to ignore TLS errors
+// TODO: Find a more elegant way (maybe in the email lib?) to do this
+func sendMail(e email.Email, s models.SMTP, tlsConfig *tls.Config) error {
+	var auth smtp.Auth
+	if s.Username != "" && s.Password != "" {
+		auth = smtp.PlainAuth("", s.Username, s.Password, strings.Split(s.Host, ":")[0])
+	}
+	// Taken from the email library
+	// Merge the To, Cc, and Bcc fields
+	to := make([]string, 0, len(e.To)+len(e.Cc)+len(e.Bcc))
+	to = append(append(append(to, e.To...), e.Cc...), e.Bcc...)
+	for i := 0; i < len(to); i++ {
+		addr, err := mail.ParseAddress(to[i])
+		if err != nil {
+			return err
+		}
+		to[i] = addr.Address
+	}
+	// Check to make sure there is at least one recipient and one "From" address
+	if e.From == "" || len(to) == 0 {
+		return errors.New("Must specify at least one From address and one To address")
+	}
+	from, err := mail.ParseAddress(e.From)
+	if err != nil {
+		return err
+	}
+	msg, err := e.Bytes()
+	if err != nil {
+		return err
+	}
+	// Taken from the standard library
+	// https://github.com/golang/go/blob/master/src/net/smtp/smtp.go#L300
+	c, err := smtp.Dial(s.Host)
+	if err != nil {
+		return err
+	}
+	defer c.Close()
+	if err = c.Hello(); err != nil {
+		return err
+	}
+	// Use TLS if available
+	if ok, _ := c.Extension("STARTTLS"); ok {
+		host, _, _ := net.SplitHostPort(s.Host)
+		/*
+			config := &tls.Config{
+				ServerName:         host,
+				InsecureSkipVerify: s.IgnoreCertErrors,
+			}*/
+		if err = c.StartTLS(tlsConfig); err != nil {
+			return err
+		}
+	}
+
+	if auth != nil {
+		if ok, _ := c.Extension("AUTH"); ok {
+			if err = c.Auth(auth); err != nil {
+				return err
+			}
+		}
+	}
+	if err = c.Mail(from); err != nil {
+		return err
+	}
+	for _, addr := range to {
+		if err = c.Rcpt(addr); err != nil {
+			return err
+		}
+	}
+	w, err := c.Data()
+	if err != nil {
+		return err
+	}
+	_, err = w.Write(msg)
+	if err != nil {
+		return err
+	}
+	err = w.Close()
+	if err != nil {
+		return err
+	}
+	return c.Quit()
+}