diff --git a/overseerr-api.yml b/overseerr-api.yml
index 81faf737..637af162 100644
--- a/overseerr-api.yml
+++ b/overseerr-api.yml
@@ -1255,6 +1255,12 @@ components:
             secure:
               type: boolean
               example: false
+            ignoreTls:
+              type: boolean
+              example: false
+            requireTls:
+              type: boolean
+              example: false
             authUser:
               type: string
               nullable: true
diff --git a/server/lib/email/index.ts b/server/lib/email/index.ts
index 9f0a9fcf..1274d6a8 100644
--- a/server/lib/email/index.ts
+++ b/server/lib/email/index.ts
@@ -13,6 +13,8 @@ class PreparedEmail extends Email {
       host: settings.options.smtpHost,
       port: settings.options.smtpPort,
       secure: settings.options.secure,
+      ignoreTLS: settings.options.ignoreTls,
+      requireTLS: settings.options.requireTls,
       tls: settings.options.allowSelfSigned
         ? {
             rejectUnauthorized: false,
@@ -26,6 +28,7 @@ class PreparedEmail extends Email {
             }
           : undefined,
     });
+
     if (pgpKey) {
       transport.use(
         'stream',
@@ -36,6 +39,7 @@ class PreparedEmail extends Email {
         })
       );
     }
+
     super({
       message: {
         from: {
diff --git a/server/lib/settings.ts b/server/lib/settings.ts
index c5390f99..a9e459b4 100644
--- a/server/lib/settings.ts
+++ b/server/lib/settings.ts
@@ -135,6 +135,8 @@ export interface NotificationAgentEmail extends NotificationAgentConfig {
     smtpHost: string;
     smtpPort: number;
     secure: boolean;
+    ignoreTls: boolean;
+    requireTls: boolean;
     authUser?: string;
     authPass?: string;
     allowSelfSigned: boolean;
@@ -275,6 +277,8 @@ class Settings {
               smtpHost: '',
               smtpPort: 587,
               secure: false,
+              ignoreTls: false,
+              requireTls: false,
               allowSelfSigned: false,
               senderName: 'Overseerr',
             },
diff --git a/src/components/Settings/Notifications/NotificationsEmail.tsx b/src/components/Settings/Notifications/NotificationsEmail.tsx
index a22c446f..a7684bf0 100644
--- a/src/components/Settings/Notifications/NotificationsEmail.tsx
+++ b/src/components/Settings/Notifications/NotificationsEmail.tsx
@@ -20,7 +20,13 @@ const messages = defineMessages({
   emailsender: 'Sender Address',
   smtpHost: 'SMTP Host',
   smtpPort: 'SMTP Port',
-  enableSsl: 'Enable SSL',
+  encryption: 'Encryption Method',
+  encryptionTip:
+    'In most cases, Implicit TLS uses port 465 and STARTTLS uses port 587',
+  encryptionNone: 'None',
+  encryptionDefault: 'Use STARTTLS if available',
+  encryptionOpportunisticTls: 'Always use STARTTLS',
+  encryptionImplicitTls: 'Use Implicit TLS',
   authUser: 'SMTP Username',
   authPass: 'SMTP Password',
   emailsettingssaved: 'Email notification settings saved successfully!',
@@ -29,8 +35,6 @@ const messages = defineMessages({
   toastEmailTestSuccess: 'Email test notification sent!',
   toastEmailTestFailed: 'Email test notification failed to send.',
   allowselfsigned: 'Allow Self-Signed Certificates',
-  ssldisabletip:
-    'SSL should be disabled on standard TLS connections (port 587)',
   senderName: 'Sender Name',
   validationEmail: 'You must provide a valid email address',
   emailNotificationTypesAlertDescription:
@@ -132,7 +136,13 @@ const NotificationsEmail: React.FC = () => {
         emailFrom: data.options.emailFrom,
         smtpHost: data.options.smtpHost,
         smtpPort: data.options.smtpPort ?? 587,
-        secure: data.options.secure,
+        encryption: data.options.secure
+          ? 'implicit'
+          : data.options.requireTls
+          ? 'opportunistic'
+          : data.options.ignoreTls
+          ? 'none'
+          : 'default',
         authUser: data.options.authUser,
         authPass: data.options.authPass,
         allowSelfSigned: data.options.allowSelfSigned,
@@ -150,7 +160,9 @@ const NotificationsEmail: React.FC = () => {
               emailFrom: values.emailFrom,
               smtpHost: values.smtpHost,
               smtpPort: Number(values.smtpPort),
-              secure: values.secure,
+              secure: values.encryption === 'implicit',
+              ignoreTls: values.encryption === 'none',
+              requireTls: values.encryption === 'opportunistic',
               authUser: values.authUser,
               authPass: values.authPass,
               allowSelfSigned: values.allowSelfSigned,
@@ -196,7 +208,9 @@ const NotificationsEmail: React.FC = () => {
                 emailFrom: values.emailFrom,
                 smtpHost: values.smtpHost,
                 smtpPort: Number(values.smtpPort),
-                secure: values.secure,
+                secure: values.encryption === 'implicit',
+                ignoreTls: values.encryption === 'none',
+                requireTls: values.encryption === 'opportunistic',
                 authUser: values.authUser,
                 authPass: values.authPass,
                 senderName: values.senderName,
@@ -339,14 +353,29 @@ const NotificationsEmail: React.FC = () => {
                 </div>
               </div>
               <div className="form-row">
-                <label htmlFor="secure" className="checkbox-label">
-                  <span>{intl.formatMessage(messages.enableSsl)}</span>
-                  <span className="label-tip">
-                    {intl.formatMessage(messages.ssldisabletip)}
-                  </span>
+                <label htmlFor="encryption" className="text-label">
+                  {intl.formatMessage(messages.encryption)}
+                  <span className="label-required">*</span>
                 </label>
                 <div className="form-input">
-                  <Field type="checkbox" id="secure" name="secure" />
+                  <div className="form-input-field">
+                    <Field as="select" id="encryption" name="encryption">
+                      <option value="none">
+                        {intl.formatMessage(messages.encryptionNone)}
+                      </option>
+                      <option value="default">
+                        {intl.formatMessage(messages.encryptionDefault)}
+                      </option>
+                      <option value="opportunistic">
+                        {intl.formatMessage(
+                          messages.encryptionOpportunisticTls
+                        )}
+                      </option>
+                      <option value="implicit">
+                        {intl.formatMessage(messages.encryptionImplicitTls)}
+                      </option>
+                    </Field>
+                  </div>
                 </div>
               </div>
               <div className="form-row">
diff --git a/src/i18n/locale/en.json b/src/i18n/locale/en.json
index 78d6388d..e31d4d78 100644
--- a/src/i18n/locale/en.json
+++ b/src/i18n/locale/en.json
@@ -327,7 +327,12 @@
   "components.Settings.Notifications.emailsender": "Sender Address",
   "components.Settings.Notifications.emailsettingsfailed": "Email notification settings failed to save.",
   "components.Settings.Notifications.emailsettingssaved": "Email notification settings saved successfully!",
-  "components.Settings.Notifications.enableSsl": "Enable SSL",
+  "components.Settings.Notifications.encryption": "Encryption Method",
+  "components.Settings.Notifications.encryptionDefault": "Use STARTTLS if available",
+  "components.Settings.Notifications.encryptionImplicitTls": "Use Implicit TLS",
+  "components.Settings.Notifications.encryptionNone": "None",
+  "components.Settings.Notifications.encryptionOpportunisticTls": "Always use STARTTLS",
+  "components.Settings.Notifications.encryptionTip": "In most cases, Implicit TLS uses port 465 and STARTTLS uses port 587",
   "components.Settings.Notifications.pgpPassword": "PGP Password",
   "components.Settings.Notifications.pgpPasswordTip": "Sign encrypted email messages using <OpenPgpLink>OpenPGP</OpenPgpLink>",
   "components.Settings.Notifications.pgpPrivateKey": "PGP Private Key",
@@ -337,7 +342,6 @@
   "components.Settings.Notifications.senderName": "Sender Name",
   "components.Settings.Notifications.smtpHost": "SMTP Host",
   "components.Settings.Notifications.smtpPort": "SMTP Port",
-  "components.Settings.Notifications.ssldisabletip": "SSL should be disabled on standard TLS connections (port 587)",
   "components.Settings.Notifications.telegramsettingsfailed": "Telegram notification settings failed to save.",
   "components.Settings.Notifications.telegramsettingssaved": "Telegram notification settings saved successfully!",
   "components.Settings.Notifications.toastDiscordTestFailed": "Discord test notification failed to send.",