diff --git a/src/modules/cmdpal/Core/Microsoft.CmdPal.Core.ViewModels/ListViewModel.cs b/src/modules/cmdpal/Core/Microsoft.CmdPal.Core.ViewModels/ListViewModel.cs
index ebfe80533f..f9d58d0e68 100644
--- a/src/modules/cmdpal/Core/Microsoft.CmdPal.Core.ViewModels/ListViewModel.cs
+++ b/src/modules/cmdpal/Core/Microsoft.CmdPal.Core.ViewModels/ListViewModel.cs
@@ -97,6 +97,17 @@ public partial class ListViewModel : PageViewModel, IDisposable
         EmptyContent = new(new(null), PageContext);
     }
 
+    private void FiltersPropertyChanged(object? sender, System.ComponentModel.PropertyChangedEventArgs e)
+    {
+        if (e.PropertyName == nameof(FiltersViewModel.Filters))
+        {
+            var filtersViewModel = sender as FiltersViewModel;
+            var hasFilters = filtersViewModel?.Filters.Length > 0;
+            HasFilters = hasFilters;
+            UpdateProperty(nameof(HasFilters));
+        }
+    }
+
     // TODO: Does this need to hop to a _different_ thread, so that we don't block the extension while we're fetching?
     private void Model_ItemsChanged(object sender, IItemsChangedEventArgs args) => FetchItems();
 
@@ -586,8 +597,11 @@ public partial class ListViewModel : PageViewModel, IDisposable
         EmptyContent = new(new(model.EmptyContent), PageContext);
         EmptyContent.SlowInitializeProperties();
 
+        Filters?.PropertyChanged -= FiltersPropertyChanged;
         Filters = new(new(model.Filters), PageContext);
-        Filters.InitializeProperties();
+        Filters?.PropertyChanged += FiltersPropertyChanged;
+
+        Filters?.InitializeProperties();
         UpdateProperty(nameof(Filters));
 
         FetchItems();
@@ -686,8 +700,10 @@ public partial class ListViewModel : PageViewModel, IDisposable
                 EmptyContent.SlowInitializeProperties();
                 break;
             case nameof(Filters):
+                Filters?.PropertyChanged -= FiltersPropertyChanged;
                 Filters = new(new(model.Filters), PageContext);
-                Filters.InitializeProperties();
+                Filters?.PropertyChanged += FiltersPropertyChanged;
+                Filters?.InitializeProperties();
                 break;
             case nameof(IsLoading):
                 UpdateEmptyContent();
@@ -757,6 +773,7 @@ public partial class ListViewModel : PageViewModel, IDisposable
             FilteredItems.Clear();
         }
 
+        Filters?.PropertyChanged -= FiltersPropertyChanged;
         Filters?.SafeCleanup();
 
         var model = _model.Unsafe;
diff --git a/src/modules/cmdpal/Core/Microsoft.CmdPal.Core.ViewModels/PageViewModel.cs b/src/modules/cmdpal/Core/Microsoft.CmdPal.Core.ViewModels/PageViewModel.cs
index 2d750c7df3..62434a632a 100644
--- a/src/modules/cmdpal/Core/Microsoft.CmdPal.Core.ViewModels/PageViewModel.cs
+++ b/src/modules/cmdpal/Core/Microsoft.CmdPal.Core.ViewModels/PageViewModel.cs
@@ -70,6 +70,8 @@ public partial class PageViewModel : ExtensionObjectViewModel, IPageContext
 
     public bool HasSearchBox { get; protected set; } = true;
 
+    public bool HasFilters { get; protected set; }
+
     public IconInfoViewModel Icon { get; protected set; }
 
     public PageViewModel(IPage? model, TaskScheduler scheduler, AppExtensionHost extensionHost)
diff --git a/src/modules/cmdpal/Microsoft.CmdPal.UI/Controls/FiltersDropDown.xaml b/src/modules/cmdpal/Microsoft.CmdPal.UI/Controls/FiltersDropDown.xaml
index 36a14965a1..f8c888e8f8 100644
--- a/src/modules/cmdpal/Microsoft.CmdPal.UI/Controls/FiltersDropDown.xaml
+++ b/src/modules/cmdpal/Microsoft.CmdPal.UI/Controls/FiltersDropDown.xaml
@@ -77,7 +77,7 @@
         SelectedValue="{x:Bind ViewModel.CurrentFilter, Mode=OneWay}"
         SelectionChanged="FiltersComboBox_SelectionChanged"
         Style="{StaticResource ComboBoxStyle}"
-        Visibility="{x:Bind ViewModel.ShouldShowFilters, Mode=OneWay, Converter={StaticResource BoolToVisibilityConverter}}">
+        Visibility="{x:Bind ViewModel.ShouldShowFilters, Mode=OneWay, Converter={StaticResource BoolToVisibilityConverter}, FallbackValue=Collapsed}">
         <ComboBox.ItemContainerStyle>
             <Style BasedOn="{StaticResource DefaultComboBoxItemStyle}" TargetType="ComboBoxItem">
                 <Setter Property="MinHeight" Value="0" />
diff --git a/src/modules/cmdpal/ext/SamplePagesExtension/Pages/IssueSpecificPages/AllIssueSamplesIndexPage.cs b/src/modules/cmdpal/ext/SamplePagesExtension/Pages/IssueSpecificPages/AllIssueSamplesIndexPage.cs
new file mode 100644
index 0000000000..42cb326178
--- /dev/null
+++ b/src/modules/cmdpal/ext/SamplePagesExtension/Pages/IssueSpecificPages/AllIssueSamplesIndexPage.cs
@@ -0,0 +1,29 @@
+// Copyright (c) Microsoft Corporation
+// The Microsoft Corporation licenses this file to you under the MIT license.
+// See the LICENSE file in the project root for more information.
+
+using Microsoft.CommandPalette.Extensions;
+using Microsoft.CommandPalette.Extensions.Toolkit;
+
+namespace SamplePagesExtension.Pages.IssueSpecificPages;
+
+internal sealed partial class AllIssueSamplesIndexPage : ListPage
+{
+    public AllIssueSamplesIndexPage()
+    {
+        Icon = new IconInfo("🐛");
+        Name = "All Issue Samples Index Page";
+    }
+
+    public override IListItem[] GetItems()
+    {
+        return new IListItem[]
+        {
+            new ListItem(new SamplePageForIssue42827_FilterDropDownStaysVisibleAfterSwitchingFromListToContentPage())
+            {
+                Title = "Issue 42827 - Filter Drop Down Stays Visible After Switching From List To Content Page",
+                Subtitle = "Repro steps: Open this page, open the filter dropdown, select a filter, navigate to a content page, navigate back to this page. The filter dropdown should be closed but it remains open.",
+            },
+        };
+    }
+}
diff --git a/src/modules/cmdpal/ext/SamplePagesExtension/Pages/IssueSpecificPages/SamplePageForIssue42827_FilterDropDownStaysVisibleAfterSwitchingFromListToContentPage.cs b/src/modules/cmdpal/ext/SamplePagesExtension/Pages/IssueSpecificPages/SamplePageForIssue42827_FilterDropDownStaysVisibleAfterSwitchingFromListToContentPage.cs
new file mode 100644
index 0000000000..4d29b56c83
--- /dev/null
+++ b/src/modules/cmdpal/ext/SamplePagesExtension/Pages/IssueSpecificPages/SamplePageForIssue42827_FilterDropDownStaysVisibleAfterSwitchingFromListToContentPage.cs
@@ -0,0 +1,76 @@
+// Copyright (c) Microsoft Corporation
+// The Microsoft Corporation licenses this file to you under the MIT license.
+// See the LICENSE file in the project root for more information.
+
+using System.Linq;
+using Microsoft.CommandPalette.Extensions;
+using Microsoft.CommandPalette.Extensions.Toolkit;
+
+namespace SamplePagesExtension.Pages.IssueSpecificPages;
+
+internal sealed partial class SamplePageForIssue42827_FilterDropDownStaysVisibleAfterSwitchingFromListToContentPage : DynamicListPage
+{
+    public SamplePageForIssue42827_FilterDropDownStaysVisibleAfterSwitchingFromListToContentPage()
+    {
+        Icon = new IconInfo(string.Empty);
+        Name = "Issue 42827 - Filters not hiding when navigating between pages";
+        IsLoading = true;
+        var filters = new SampleFilters();
+        filters.PropChanged += Filters_PropChanged;
+        Filters = filters;
+    }
+
+    private void Filters_PropChanged(object sender, IPropChangedEventArgs args) => RaiseItemsChanged();
+
+    public override void UpdateSearchText(string oldSearch, string newSearch) => RaiseItemsChanged();
+
+    public override IListItem[] GetItems()
+    {
+        var items = SearchText.ToCharArray().Select(ch => new ListItem(new SampleContentPage()) { Title = ch.ToString() }).ToArray();
+        if (items.Length == 0)
+        {
+            items = [
+                new ListItem(new SampleContentPage()) { Title = "This List item will open a content page" },
+                new ListItem(new SampleContentPage()) { Title = "This List item will open a content page too" },
+                new ListItem(new SampleContentPage()) { Title = "Guess what this one will do?" },
+            ];
+        }
+
+        if (!string.IsNullOrEmpty(Filters.CurrentFilterId))
+        {
+            switch (Filters.CurrentFilterId)
+            {
+                case "mod2":
+                    items = items.Where((item, index) => (index + 1) % 2 == 0).ToArray();
+                    break;
+                case "mod3":
+                    items = items.Where((item, index) => (index + 1) % 3 == 0).ToArray();
+                    break;
+                case "all":
+                default:
+                    // No filtering
+                    break;
+            }
+        }
+
+        foreach (var item in items)
+        {
+            item.Subtitle = "Filter drop-down should be hidden when navigating to a content page";
+        }
+
+        return items;
+    }
+
+    internal sealed partial class SampleFilters : Filters
+    {
+        public override IFilterItem[] GetFilters()
+        {
+            return
+            [
+                new Filter() { Id = "all", Name = "All" },
+                new Filter() { Id = "mod2", Name = "Every 2nd", Icon = new IconInfo("2") },
+                new Filter() { Id = "mod3", Name = "Every 3rd (and long name)", Icon = new IconInfo("3") },
+            ];
+        }
+    }
+}
diff --git a/src/modules/cmdpal/ext/SamplePagesExtension/SamplesListPage.cs b/src/modules/cmdpal/ext/SamplePagesExtension/SamplesListPage.cs
index ef3a027f4f..254dbf3eb9 100644
--- a/src/modules/cmdpal/ext/SamplePagesExtension/SamplesListPage.cs
+++ b/src/modules/cmdpal/ext/SamplePagesExtension/SamplesListPage.cs
@@ -5,6 +5,7 @@
 using Microsoft.CommandPalette.Extensions;
 using Microsoft.CommandPalette.Extensions.Toolkit;
 using SamplePagesExtension.Pages;
+using SamplePagesExtension.Pages.IssueSpecificPages;
 
 namespace SamplePagesExtension;
 
@@ -106,6 +107,11 @@ public partial class SamplesListPage : ListPage
         {
             Title = "Evil samples",
             Subtitle = "Samples designed to break the palette in many different evil ways",
+        },
+        new ListItem(new AllIssueSamplesIndexPage())
+        {
+            Title = "Issue-specific samples",
+            Subtitle = "Samples designed to reproduce specific issues",
         }
     ];