diff --git a/frontend/src/Settings/MediaManagement/MediaManagement.js b/frontend/src/Settings/MediaManagement/MediaManagement.js
index d1881c068..627263fff 100644
--- a/frontend/src/Settings/MediaManagement/MediaManagement.js
+++ b/frontend/src/Settings/MediaManagement/MediaManagement.js
@@ -191,26 +191,21 @@ class MediaManagement extends Component {
                     <FieldSet
                       legend={translate('Importing')}
                     >
-                      {
-                        !isWindows &&
-                          <FormGroup
-                            advancedSettings={advancedSettings}
-                            isAdvanced={true}
-                            size={sizes.MEDIUM}
-                          >
-                            <FormLabel>
-                              {translate('SkipFreeSpaceCheck')}
-                            </FormLabel>
+                      <FormGroup
+                        advancedSettings={advancedSettings}
+                        isAdvanced={true}
+                        size={sizes.MEDIUM}
+                      >
+                        <FormLabel>{translate('SkipFreeSpaceCheck')}</FormLabel>
 
-                            <FormInputGroup
-                              type={inputTypes.CHECK}
-                              name="skipFreeSpaceCheckWhenImporting"
-                              helpText={translate('SkipFreeSpaceCheckWhenImportingHelpText')}
-                              onChange={onInputChange}
-                              {...settings.skipFreeSpaceCheckWhenImporting}
-                            />
-                          </FormGroup>
-                      }
+                        <FormInputGroup
+                          type={inputTypes.CHECK}
+                          name="skipFreeSpaceCheckWhenImporting"
+                          helpText={translate('SkipFreeSpaceCheckHelpText')}
+                          onChange={onInputChange}
+                          {...settings.skipFreeSpaceCheckWhenImporting}
+                        />
+                      </FormGroup>
 
                       <FormGroup
                         advancedSettings={advancedSettings}
diff --git a/src/NzbDrone.Core.Test/DecisionEngineTests/FreeSpaceSpecificationFixture.cs b/src/NzbDrone.Core.Test/DecisionEngineTests/FreeSpaceSpecificationFixture.cs
new file mode 100644
index 000000000..c6d3e8680
--- /dev/null
+++ b/src/NzbDrone.Core.Test/DecisionEngineTests/FreeSpaceSpecificationFixture.cs
@@ -0,0 +1,95 @@
+using FluentAssertions;
+using Moq;
+using NUnit.Framework;
+using NzbDrone.Common.Disk;
+using NzbDrone.Common.Extensions;
+using NzbDrone.Core.Configuration;
+using NzbDrone.Core.DecisionEngine.Specifications;
+using NzbDrone.Core.Music;
+using NzbDrone.Core.Parser.Model;
+using NzbDrone.Core.Test.Framework;
+using NzbDrone.Test.Common;
+
+namespace NzbDrone.Core.Test.DecisionEngineTests
+{
+    [TestFixture]
+    public class FreeSpaceSpecificationFixture : CoreTest<FreeSpaceSpecification>
+    {
+        private RemoteAlbum _remoteAlbum;
+
+        [SetUp]
+        public void Setup()
+        {
+            _remoteAlbum = new RemoteAlbum() { Release = new ReleaseInfo(), Artist = new Artist { Path = @"C:\Test\Music\Artist".AsOsAgnostic() } };
+        }
+
+        private void WithMinimumFreeSpace(int size)
+        {
+            Mocker.GetMock<IConfigService>().SetupGet(c => c.MinimumFreeSpaceWhenImporting).Returns(size);
+        }
+
+        private void WithAvailableSpace(int size)
+        {
+            Mocker.GetMock<IDiskProvider>().Setup(s => s.GetAvailableSpace(It.IsAny<string>())).Returns(size.Megabytes());
+        }
+
+        private void WithSize(int size)
+        {
+            _remoteAlbum.Release.Size = size.Megabytes();
+        }
+
+        [Test]
+        public void should_return_true_when_available_space_is_more_than_size()
+        {
+            WithMinimumFreeSpace(0);
+            WithAvailableSpace(200);
+            WithSize(100);
+
+            Subject.IsSatisfiedBy(_remoteAlbum, null).Accepted.Should().BeTrue();
+        }
+
+        [Test]
+        public void should_return_true_when_available_space_minus_size_is_more_than_minimum_free_space()
+        {
+            WithMinimumFreeSpace(50);
+            WithAvailableSpace(200);
+            WithSize(100);
+
+            Subject.IsSatisfiedBy(_remoteAlbum, null).Accepted.Should().BeTrue();
+        }
+
+        [Test]
+        public void should_return_false_available_space_is_less_than_size()
+        {
+            WithMinimumFreeSpace(0);
+            WithAvailableSpace(200);
+            WithSize(1000);
+
+            Subject.IsSatisfiedBy(_remoteAlbum, null).Accepted.Should().BeFalse();
+        }
+
+        [Test]
+        public void should_return_false_when_available_space_minus_size_is_less_than_minimum_free_space()
+        {
+            WithMinimumFreeSpace(150);
+            WithAvailableSpace(200);
+            WithSize(100);
+
+            Subject.IsSatisfiedBy(_remoteAlbum, null).Accepted.Should().BeFalse();
+        }
+
+        [Test]
+        public void should_return_true_if_skip_free_space_check_is_true()
+        {
+            Mocker.GetMock<IConfigService>()
+                .Setup(s => s.SkipFreeSpaceCheckWhenImporting)
+                .Returns(true);
+
+            WithMinimumFreeSpace(150);
+            WithAvailableSpace(200);
+            WithSize(100);
+
+            Subject.IsSatisfiedBy(_remoteAlbum, null).Accepted.Should().BeTrue();
+        }
+    }
+}
diff --git a/src/NzbDrone.Core/Configuration/ConfigService.cs b/src/NzbDrone.Core/Configuration/ConfigService.cs
index 6aa7c5448..239f000d6 100644
--- a/src/NzbDrone.Core/Configuration/ConfigService.cs
+++ b/src/NzbDrone.Core/Configuration/ConfigService.cs
@@ -185,6 +185,7 @@ namespace NzbDrone.Core.Configuration
             set { SetValue("DownloadClientHistoryLimit", value); }
         }
 
+        // TODO: Rename to 'Skip Free Space Check'
         public bool SkipFreeSpaceCheckWhenImporting
         {
             get { return GetValueBoolean("SkipFreeSpaceCheckWhenImporting", false); }
diff --git a/src/NzbDrone.Core/DecisionEngine/Specifications/FreeSpaceSpecification.cs b/src/NzbDrone.Core/DecisionEngine/Specifications/FreeSpaceSpecification.cs
new file mode 100644
index 000000000..d83629e08
--- /dev/null
+++ b/src/NzbDrone.Core/DecisionEngine/Specifications/FreeSpaceSpecification.cs
@@ -0,0 +1,66 @@
+using NLog;
+using NzbDrone.Common.Disk;
+using NzbDrone.Common.Extensions;
+using NzbDrone.Core.Configuration;
+using NzbDrone.Core.IndexerSearch.Definitions;
+using NzbDrone.Core.Parser.Model;
+
+namespace NzbDrone.Core.DecisionEngine.Specifications
+{
+    public class FreeSpaceSpecification : IDecisionEngineSpecification
+    {
+        private readonly IConfigService _configService;
+        private readonly IDiskProvider _diskProvider;
+        private readonly Logger _logger;
+
+        public FreeSpaceSpecification(IConfigService configService, IDiskProvider diskProvider, Logger logger)
+        {
+            _configService = configService;
+            _diskProvider = diskProvider;
+            _logger = logger;
+        }
+
+        public SpecificationPriority Priority => SpecificationPriority.Default;
+        public RejectionType Type => RejectionType.Permanent;
+
+        public Decision IsSatisfiedBy(RemoteAlbum subject, SearchCriteriaBase searchCriteria)
+        {
+            if (_configService.SkipFreeSpaceCheckWhenImporting)
+            {
+                _logger.Debug("Skipping free space check");
+                return Decision.Accept();
+            }
+
+            var size = subject.Release.Size;
+            var freeSpace = _diskProvider.GetAvailableSpace(subject.Artist.Path);
+
+            if (!freeSpace.HasValue)
+            {
+                _logger.Debug("Unable to get available space for {0}. Skipping", subject.Artist.Path);
+
+                return Decision.Accept();
+            }
+
+            var minimumSpace = _configService.MinimumFreeSpaceWhenImporting.Megabytes();
+            var remainingSpace = freeSpace.Value - size;
+
+            if (remainingSpace <= 0)
+            {
+                var message = "Importing after download will exceed available disk space";
+
+                _logger.Debug(message);
+                return Decision.Reject(message);
+            }
+
+            if (remainingSpace < minimumSpace)
+            {
+                var message = $"Not enough free space ({minimumSpace.SizeSuffix()}) to import after download: {remainingSpace.SizeSuffix()}. (Settings: Media Management: Minimum Free Space)";
+
+                _logger.Debug(message);
+                return Decision.Reject(message);
+            }
+
+            return Decision.Accept();
+        }
+    }
+}
diff --git a/src/NzbDrone.Core/Localization/Core/en.json b/src/NzbDrone.Core/Localization/Core/en.json
index 0936742c7..81cdb9c3f 100644
--- a/src/NzbDrone.Core/Localization/Core/en.json
+++ b/src/NzbDrone.Core/Localization/Core/en.json
@@ -1127,7 +1127,7 @@
   "SizeLimit": "Size Limit",
   "SizeOnDisk": "Size on Disk",
   "SkipFreeSpaceCheck": "Skip Free Space Check",
-  "SkipFreeSpaceCheckWhenImportingHelpText": "Use when {appName} is unable to detect free space of your root folder during file import",
+  "SkipFreeSpaceCheckHelpText": "Use when {appName} is unable to detect free space of your root folder",
   "SkipRedownload": "Skip Redownload",
   "SkipRedownloadHelpText": "Prevents {appName} from trying download alternative releases for the removed items",
   "Small": "Small",