diff --git a/src/components/Settings/RadarrModal/index.tsx b/src/components/Settings/RadarrModal/index.tsx
index 59f16065d..51c74ba89 100644
--- a/src/components/Settings/RadarrModal/index.tsx
+++ b/src/components/Settings/RadarrModal/index.tsx
@@ -130,7 +130,10 @@ const RadarrModal = ({ onClose, radarr, onSave }: RadarrModalProps) => {
       intl.formatMessage(messages.validationMinimumAvailabilityRequired)
     ),
     externalUrl: Yup.string()
-      .url(intl.formatMessage(messages.validationApplicationUrl))
+      .matches(
+        /^https?:\/\/(www\.)?[-a-zA-Z0-9@:%._+~#=]{1,256}(\.[a-zA-Z0-9()]{1,6}\b([-a-zA-Z0-9()@:%_+.~#?&/=]*))?$/i,
+        intl.formatMessage(messages.validationApplicationUrl)
+      )
       .test(
         'no-trailing-slash',
         intl.formatMessage(messages.validationApplicationUrlTrailingSlash),
diff --git a/src/components/Settings/SettingsJellyfin.tsx b/src/components/Settings/SettingsJellyfin.tsx
index 316dc48ef..7c6d02d80 100644
--- a/src/components/Settings/SettingsJellyfin.tsx
+++ b/src/components/Settings/SettingsJellyfin.tsx
@@ -139,7 +139,10 @@ const SettingsJellyfin: React.FC<SettingsJellyfinProps> = ({
       ),
     jellyfinExternalUrl: Yup.string()
       .nullable()
-      .url(intl.formatMessage(messages.validationUrl))
+      .matches(
+        /^https?:\/\/(www\.)?[-a-zA-Z0-9@:%._+~#=]{1,256}(\.[a-zA-Z0-9()]{1,6}\b([-a-zA-Z0-9()@:%_+.~#?&/=]*))?$/i,
+        intl.formatMessage(messages.validationUrl)
+      )
       .test(
         'no-trailing-slash',
         intl.formatMessage(messages.validationUrlTrailingSlash),
@@ -147,7 +150,10 @@ const SettingsJellyfin: React.FC<SettingsJellyfinProps> = ({
       ),
     jellyfinForgotPasswordUrl: Yup.string()
       .nullable()
-      .url(intl.formatMessage(messages.validationUrl))
+      .matches(
+        /^https?:\/\/(www\.)?[-a-zA-Z0-9@:%._+~#=]{1,256}(\.[a-zA-Z0-9()]{1,6}\b([-a-zA-Z0-9()@:%_+.~#?&/=]*))?$/i,
+        intl.formatMessage(messages.validationUrl)
+      )
       .test(
         'no-trailing-slash',
         intl.formatMessage(messages.validationUrlTrailingSlash),
diff --git a/src/components/Settings/SettingsMain/index.tsx b/src/components/Settings/SettingsMain/index.tsx
index 2d1e0219f..41f399ad5 100644
--- a/src/components/Settings/SettingsMain/index.tsx
+++ b/src/components/Settings/SettingsMain/index.tsx
@@ -87,7 +87,10 @@ const SettingsMain = () => {
       intl.formatMessage(messages.validationApplicationTitle)
     ),
     applicationUrl: Yup.string()
-      .url(intl.formatMessage(messages.validationApplicationUrl))
+      .matches(
+        /^https?:\/\/(www\.)?[-a-zA-Z0-9@:%._+~#=]{1,256}(\.[a-zA-Z0-9()]{1,6}\b([-a-zA-Z0-9()@:%_+.~#?&/=]*))?$/i,
+        intl.formatMessage(messages.validationApplicationUrl)
+      )
       .test(
         'no-trailing-slash',
         intl.formatMessage(messages.validationApplicationUrlTrailingSlash),
diff --git a/src/components/Settings/SettingsPlex.tsx b/src/components/Settings/SettingsPlex.tsx
index a20fc4836..82cabe92f 100644
--- a/src/components/Settings/SettingsPlex.tsx
+++ b/src/components/Settings/SettingsPlex.tsx
@@ -190,7 +190,10 @@ const SettingsPlex = ({ onComplete }: SettingsPlexProps) => {
         otherwise: Yup.string().nullable(),
       }),
       tautulliExternalUrl: Yup.string()
-        .url(intl.formatMessage(messages.validationUrl))
+        .matches(
+          /^https?:\/\/(www\.)?[-a-zA-Z0-9@:%._+~#=]{1,256}(\.[a-zA-Z0-9()]{1,6}\b([-a-zA-Z0-9()@:%_+.~#?&/=]*))?$/i,
+          intl.formatMessage(messages.validationUrl)
+        )
         .test(
           'no-trailing-slash',
           intl.formatMessage(messages.validationUrlTrailingSlash),
diff --git a/src/components/Settings/SonarrModal/index.tsx b/src/components/Settings/SonarrModal/index.tsx
index f2bcd4dbc..7890d4b5c 100644
--- a/src/components/Settings/SonarrModal/index.tsx
+++ b/src/components/Settings/SonarrModal/index.tsx
@@ -145,7 +145,10 @@ const SonarrModal = ({ onClose, sonarr, onSave }: SonarrModalProps) => {
         )
       : Yup.number(),
     externalUrl: Yup.string()
-      .url(intl.formatMessage(messages.validationApplicationUrl))
+      .matches(
+        /^https?:\/\/(www\.)?[-a-zA-Z0-9@:%._+~#=]{1,256}(\.[a-zA-Z0-9()]{1,6}\b([-a-zA-Z0-9()@:%_+.~#?&/=]*))?$/i,
+        intl.formatMessage(messages.validationApplicationUrl)
+      )
       .test(
         'no-trailing-slash',
         intl.formatMessage(messages.validationApplicationUrlTrailingSlash),