diff --git a/frontend/src/AddSeries/SeriesMonitoringOptionsPopoverContent.js b/frontend/src/AddSeries/SeriesMonitoringOptionsPopoverContent.js
index e889fbb09..6a08f05af 100644
--- a/frontend/src/AddSeries/SeriesMonitoringOptionsPopoverContent.js
+++ b/frontend/src/AddSeries/SeriesMonitoringOptionsPopoverContent.js
@@ -35,6 +35,16 @@ function SeriesMonitoringOptionsPopoverContent() {
         data="Monitor all episodes of the latest season and future seasons"
       />
 
+      <DescriptionListItem
+        title="Monitor Specials"
+        data="Monitor all special episodes without changing the monitored status of other episodes"
+      />
+
+      <DescriptionListItem
+        title="Unmonitor Specials"
+        data="Unmonitor all special episodes without changing the monitored status of other episodes"
+      />
+
       <DescriptionListItem
         title="None"
         data="No episodes will be monitored"
diff --git a/frontend/src/Series/Index/Select/SeasonPass/ChangeMonitoringModalContent.css b/frontend/src/Series/Index/Select/SeasonPass/ChangeMonitoringModalContent.css
index ea406894e..1963dbd44 100644
--- a/frontend/src/Series/Index/Select/SeasonPass/ChangeMonitoringModalContent.css
+++ b/frontend/src/Series/Index/Select/SeasonPass/ChangeMonitoringModalContent.css
@@ -8,6 +8,10 @@
   font-weight: bold;
 }
 
+.labelIcon {
+  margin-left: 8px;
+}
+
 @media only screen and (max-width: $breakpointExtraSmall) {
   .modalFooter {
     flex-direction: column;
diff --git a/frontend/src/Series/Index/Select/SeasonPass/ChangeMonitoringModalContent.css.d.ts b/frontend/src/Series/Index/Select/SeasonPass/ChangeMonitoringModalContent.css.d.ts
index cbf2d6328..e7b140ccb 100644
--- a/frontend/src/Series/Index/Select/SeasonPass/ChangeMonitoringModalContent.css.d.ts
+++ b/frontend/src/Series/Index/Select/SeasonPass/ChangeMonitoringModalContent.css.d.ts
@@ -1,6 +1,7 @@
 // This file is automatically generated.
 // Please do not change this file!
 interface CssExports {
+  'labelIcon': string;
   'modalFooter': string;
   'selected': string;
 }
diff --git a/frontend/src/Series/Index/Select/SeasonPass/ChangeMonitoringModalContent.tsx b/frontend/src/Series/Index/Select/SeasonPass/ChangeMonitoringModalContent.tsx
index e7a874b15..8fce3f4c8 100644
--- a/frontend/src/Series/Index/Select/SeasonPass/ChangeMonitoringModalContent.tsx
+++ b/frontend/src/Series/Index/Select/SeasonPass/ChangeMonitoringModalContent.tsx
@@ -1,14 +1,17 @@
 import React, { useCallback, useState } from 'react';
+import SeriesMonitoringOptionsPopoverContent from 'AddSeries/SeriesMonitoringOptionsPopoverContent';
 import Form from 'Components/Form/Form';
 import FormGroup from 'Components/Form/FormGroup';
 import FormInputGroup from 'Components/Form/FormInputGroup';
 import FormLabel from 'Components/Form/FormLabel';
+import Icon from 'Components/Icon';
 import Button from 'Components/Link/Button';
 import ModalBody from 'Components/Modal/ModalBody';
 import ModalContent from 'Components/Modal/ModalContent';
 import ModalFooter from 'Components/Modal/ModalFooter';
 import ModalHeader from 'Components/Modal/ModalHeader';
-import { inputTypes } from 'Helpers/Props';
+import Popover from 'Components/Tooltip/Popover';
+import { icons, inputTypes, tooltipPositions } from 'Helpers/Props';
 import translate from 'Utilities/String/translate';
 import styles from './ChangeMonitoringModalContent.css';
 
@@ -48,7 +51,16 @@ function ChangeMonitoringModalContent(
       <ModalBody>
         <Form {...otherProps}>
           <FormGroup>
-            <FormLabel>{translate('Monitoring')}</FormLabel>
+            <FormLabel>
+              {translate('Monitoring')}
+
+              <Popover
+                anchor={<Icon className={styles.labelIcon} name={icons.INFO} />}
+                title={translate('Monitoring Options')}
+                body={<SeriesMonitoringOptionsPopoverContent />}
+                position={tooltipPositions.RIGHT}
+              />
+            </FormLabel>
 
             <FormInputGroup
               type={inputTypes.MONITOR_EPISODES_SELECT}
diff --git a/frontend/src/Series/MonitoringOptions/MonitoringOptionsModalContent.css b/frontend/src/Series/MonitoringOptions/MonitoringOptionsModalContent.css
new file mode 100644
index 000000000..b9d93010e
--- /dev/null
+++ b/frontend/src/Series/MonitoringOptions/MonitoringOptionsModalContent.css
@@ -0,0 +1,3 @@
+.labelIcon {
+  margin-left: 8px;
+}
diff --git a/frontend/src/Series/MonitoringOptions/MonitoringOptionsModalContent.css.d.ts b/frontend/src/Series/MonitoringOptions/MonitoringOptionsModalContent.css.d.ts
new file mode 100644
index 000000000..a38c33c2a
--- /dev/null
+++ b/frontend/src/Series/MonitoringOptions/MonitoringOptionsModalContent.css.d.ts
@@ -0,0 +1,7 @@
+// This file is automatically generated.
+// Please do not change this file!
+interface CssExports {
+  'labelIcon': string;
+}
+export const cssExports: CssExports;
+export default cssExports;
diff --git a/frontend/src/Series/MonitoringOptions/MonitoringOptionsModalContent.js b/frontend/src/Series/MonitoringOptions/MonitoringOptionsModalContent.js
index bd69e53a2..de66da5fb 100644
--- a/frontend/src/Series/MonitoringOptions/MonitoringOptionsModalContent.js
+++ b/frontend/src/Series/MonitoringOptions/MonitoringOptionsModalContent.js
@@ -1,16 +1,20 @@
 import PropTypes from 'prop-types';
 import React, { Component } from 'react';
+import SeriesMonitoringOptionsPopoverContent from 'AddSeries/SeriesMonitoringOptionsPopoverContent';
 import Form from 'Components/Form/Form';
 import FormGroup from 'Components/Form/FormGroup';
 import FormInputGroup from 'Components/Form/FormInputGroup';
 import FormLabel from 'Components/Form/FormLabel';
+import Icon from 'Components/Icon';
 import Button from 'Components/Link/Button';
 import SpinnerButton from 'Components/Link/SpinnerButton';
 import ModalBody from 'Components/Modal/ModalBody';
 import ModalContent from 'Components/Modal/ModalContent';
 import ModalFooter from 'Components/Modal/ModalFooter';
 import ModalHeader from 'Components/Modal/ModalHeader';
-import { inputTypes } from 'Helpers/Props';
+import Popover from 'Components/Tooltip/Popover';
+import { icons, inputTypes, tooltipPositions } from 'Helpers/Props';
+import styles from './MonitoringOptionsModalContent.css';
 
 const NO_CHANGE = 'noChange';
 
@@ -84,7 +88,21 @@ class MonitoringOptionsModalContent extends Component {
         <ModalBody>
           <Form {...otherProps}>
             <FormGroup>
-              <FormLabel>Monitoring</FormLabel>
+              <FormLabel>
+                Monitoring
+
+                <Popover
+                  anchor={
+                    <Icon
+                      className={styles.labelIcon}
+                      name={icons.INFO}
+                    />
+                  }
+                  title="Monitoring Options"
+                  body={<SeriesMonitoringOptionsPopoverContent />}
+                  position={tooltipPositions.RIGHT}
+                />
+              </FormLabel>
 
               <FormInputGroup
                 type={inputTypes.MONITOR_EPISODES_SELECT}
diff --git a/frontend/src/Utilities/Series/monitorOptions.js b/frontend/src/Utilities/Series/monitorOptions.js
index 9c59fb131..4a53343c3 100644
--- a/frontend/src/Utilities/Series/monitorOptions.js
+++ b/frontend/src/Utilities/Series/monitorOptions.js
@@ -6,6 +6,8 @@ const monitorOptions = [
   { key: 'pilot', value: 'Pilot Episode' },
   { key: 'firstSeason', value: 'Only First Season' },
   { key: 'latestSeason', value: 'Only Latest Season' },
+  { key: 'monitorSpecials', value: 'Monitor Specials' },
+  { key: 'unmonitorSpecials', value: 'Unmonitor Specials' },
   { key: 'none', value: 'None' }
 ];
 
diff --git a/src/NzbDrone.Core.Test/TvTests/EpisodeMonitoredServiceTests/SetEpisodeMontitoredFixture.cs b/src/NzbDrone.Core.Test/TvTests/EpisodeMonitoredServiceTests/SetEpisodeMontitoredFixture.cs
index f018825d9..0ad93ce7e 100644
--- a/src/NzbDrone.Core.Test/TvTests/EpisodeMonitoredServiceTests/SetEpisodeMontitoredFixture.cs
+++ b/src/NzbDrone.Core.Test/TvTests/EpisodeMonitoredServiceTests/SetEpisodeMontitoredFixture.cs
@@ -149,6 +149,58 @@ namespace NzbDrone.Core.Test.TvTests.EpisodeMonitoredServiceTests
             VerifyNotMonitored(e => e.SeasonNumber == 0);
         }
 
+        [Test]
+        public void should_monitor_specials()
+        {
+            GivenSpecials();
+
+            var monitoringOptions = new MonitoringOptions
+            {
+                Monitor = MonitorTypes.MonitorSpecials
+            };
+
+            Subject.SetEpisodeMonitoredStatus(_series, monitoringOptions);
+
+            VerifyMonitored(e => e.SeasonNumber == 0);
+        }
+
+        [Test]
+        public void should_unmonitor_specials()
+        {
+            GivenSpecials();
+
+            var monitoringOptions = new MonitoringOptions
+            {
+                Monitor = MonitorTypes.UnmonitorSpecials
+            };
+
+            Subject.SetEpisodeMonitoredStatus(_series, monitoringOptions);
+
+            VerifyNotMonitored(e => e.SeasonNumber == 0);
+        }
+
+        [Test]
+        public void should_unmonitor_specials_after_monitoring()
+        {
+            GivenSpecials();
+
+            var monitoringOptions = new MonitoringOptions
+            {
+                Monitor = MonitorTypes.MonitorSpecials
+            };
+
+            Subject.SetEpisodeMonitoredStatus(_series, monitoringOptions);
+
+            monitoringOptions = new MonitoringOptions
+            {
+                Monitor = MonitorTypes.UnmonitorSpecials
+            };
+
+            Subject.SetEpisodeMonitoredStatus(_series, monitoringOptions);
+
+            VerifyNotMonitored(e => e.SeasonNumber == 0);
+        }
+
         [Test]
         public void should_not_monitor_season_when_all_episodes_are_monitored_except_latest_season()
         {
diff --git a/src/NzbDrone.Core/Tv/EpisodeMonitoredService.cs b/src/NzbDrone.Core/Tv/EpisodeMonitoredService.cs
index eaf1a6235..c0351457a 100644
--- a/src/NzbDrone.Core/Tv/EpisodeMonitoredService.cs
+++ b/src/NzbDrone.Core/Tv/EpisodeMonitoredService.cs
@@ -100,6 +100,18 @@ namespace NzbDrone.Core.Tv
 
                     break;
 
+                case MonitorTypes.MonitorSpecials:
+                    _logger.Debug("[{0}] Monitoring special episodes", series.Title);
+                    ToggleEpisodesMonitoredState(episodes.Where(e => e.SeasonNumber == 0), true);
+
+                    break;
+
+                case MonitorTypes.UnmonitorSpecials:
+                    _logger.Debug("[{0}] Unmonitoring special episodes", series.Title);
+                    ToggleEpisodesMonitoredState(episodes.Where(e => e.SeasonNumber == 0), false);
+
+                    break;
+
                 case MonitorTypes.None:
                     _logger.Debug("[{0}] Unmonitoring all episodes", series.Title);
                     ToggleEpisodesMonitoredState(episodes, e => false);
diff --git a/src/NzbDrone.Core/Tv/MonitoringOptions.cs b/src/NzbDrone.Core/Tv/MonitoringOptions.cs
index 9ac1d7710..878a9f8e1 100644
--- a/src/NzbDrone.Core/Tv/MonitoringOptions.cs
+++ b/src/NzbDrone.Core/Tv/MonitoringOptions.cs
@@ -19,6 +19,8 @@ namespace NzbDrone.Core.Tv
         FirstSeason,
         LatestSeason,
         Pilot,
+        MonitorSpecials,
+        UnmonitorSpecials,
         None
     }
 }
diff --git a/src/Sonarr.Api.V3/openapi.json b/src/Sonarr.Api.V3/openapi.json
index 0a6d4ebcc..6b4c5c624 100644
--- a/src/Sonarr.Api.V3/openapi.json
+++ b/src/Sonarr.Api.V3/openapi.json
@@ -9150,6 +9150,8 @@
           "firstSeason",
           "latestSeason",
           "pilot",
+          "monitorSpecials",
+          "UnmonitorSpecials",
           "none"
         ],
         "type": "string"