diff --git a/.github/actions/spell-check/dictionary/microsoft.txt b/.github/actions/spell-check/dictionary/microsoft.txt
index 0e94847f887..2f520a5c2f3 100644
--- a/.github/actions/spell-check/dictionary/microsoft.txt
+++ b/.github/actions/spell-check/dictionary/microsoft.txt
@@ -18,6 +18,7 @@ pgo
 pgosweep
 powerrename
 powershell
+propkey
 pscustomobject
 robocopy
 SACLs
diff --git a/src/cascadia/TerminalApp/AppLogic.cpp b/src/cascadia/TerminalApp/AppLogic.cpp
index 2a02e80dd13..2c217e50b7c 100644
--- a/src/cascadia/TerminalApp/AppLogic.cpp
+++ b/src/cascadia/TerminalApp/AppLogic.cpp
@@ -693,6 +693,8 @@ namespace winrt::TerminalApp::implementation
 
         // Register for directory change notification.
         _RegisterSettingsChange();
+
+        Jumplist::UpdateJumplist(*_settings);
     }
 
     // Method Description:
@@ -851,6 +853,8 @@ namespace winrt::TerminalApp::implementation
 
         _RefreshThemeRoutine();
         _ApplyStartupTaskStateChange();
+
+        Jumplist::UpdateJumplist(*_settings);
     }
 
     // Method Description:
diff --git a/src/cascadia/TerminalApp/AppLogic.h b/src/cascadia/TerminalApp/AppLogic.h
index a5e811a886b..18204401fdc 100644
--- a/src/cascadia/TerminalApp/AppLogic.h
+++ b/src/cascadia/TerminalApp/AppLogic.h
@@ -8,6 +8,7 @@
 #include "Tab.h"
 #include "CascadiaSettings.h"
 #include "TerminalPage.h"
+#include "Jumplist.h"
 #include "../../cascadia/inc/cppwinrt_utils.h"
 
 namespace winrt::TerminalApp::implementation
diff --git a/src/cascadia/TerminalApp/Jumplist.cpp b/src/cascadia/TerminalApp/Jumplist.cpp
new file mode 100644
index 00000000000..625367c7410
--- /dev/null
+++ b/src/cascadia/TerminalApp/Jumplist.cpp
@@ -0,0 +1,131 @@
+// Copyright (c) Microsoft Corporation.
+// Licensed under the MIT license.
+
+#include "pch.h"
+#include "Jumplist.h"
+
+#include <ShObjIdl.h>
+#include <Propkey.h>
+
+using namespace winrt::TerminalApp;
+
+//  This property key isn't already defined in propkey.h, but is used by UWP Jumplist to determine the icon of the jumplist item.
+//  IShellLink's SetIconLocation isn't going to read "ms-appx://" icon paths, so we'll need to use this to set the icon.
+DEFINE_PROPERTYKEY(PKEY_AppUserModel_DestListLogoUri, 0x9F4C2855, 0x9F79, 0x4B39, 0xA8, 0xD0, 0xE1, 0xD4, 0x2D, 0xE1, 0xD5, 0xF3, 29);
+#define INIT_PKEY_AppUserModel_DestListLogoUri                                             \
+    {                                                                                      \
+        { 0x9F4C2855, 0x9F79, 0x4B39, 0xA8, 0xD0, 0xE1, 0xD4, 0x2D, 0xE1, 0xD5, 0xF3 }, 29 \
+    }
+
+// Method Description:
+// - Updates the items of the Jumplist based on the given settings.
+// Arguments:
+// - settings - The settings object to update the jumplist with.
+// Return Value:
+// - <none>
+HRESULT Jumplist::UpdateJumplist(const TerminalApp::CascadiaSettings& settings) noexcept
+{
+    try
+    {
+        auto jumplistInstance = winrt::create_instance<ICustomDestinationList>(CLSID_DestinationList, CLSCTX_ALL);
+
+        // Start the Jumplist edit transaction
+        uint32_t slots;
+        winrt::com_ptr<IObjectCollection> jumplistItems;
+        jumplistItems.capture(jumplistInstance, &ICustomDestinationList::BeginList, &slots);
+
+        // It's easier to clear the list and re-add everything. The settings aren't
+        // updated often, and there likely isn't a huge amount of items to add.
+        RETURN_IF_FAILED(jumplistItems->Clear());
+
+        // Update the list of profiles.
+        RETURN_IF_FAILED(_updateProfiles(jumplistItems.get(), settings.GetProfiles()));
+
+        // TODO GH#1571: Add items from the future customizable new tab dropdown as well.
+        // This could either replace the default profiles, or be added alongside them.
+
+        // Add the items to the jumplist Task section.
+        // The Tasks section is immutable by the user, unlike the destinations
+        // section that can have its items pinned and removed.
+        RETURN_IF_FAILED(jumplistInstance->AddUserTasks(jumplistItems.get()));
+
+        RETURN_IF_FAILED(jumplistInstance->CommitList());
+
+        return S_OK;
+    }
+    CATCH_RETURN();
+}
+
+// Method Description:
+// - Creates and adds a ShellLink object to the Jumplist for each profile.
+// Arguments:
+// - jumplistItems - The jumplist item list
+// - profiles - The profiles to add to the jumplist
+// Return Value:
+// - S_OK or HRESULT failure code.
+[[nodiscard]] HRESULT Jumplist::_updateProfiles(IObjectCollection* jumplistItems, const gsl::span<const Profile>& profiles) noexcept
+{
+    try
+    {
+        for (const auto& profile : profiles)
+        {
+            // Craft the arguments following "wt.exe"
+            auto args = fmt::format(L"-p {}", to_hstring(profile.Guid()));
+
+            // Create the shell link object for the profile
+            winrt::com_ptr<IShellLinkW> shLink;
+            RETURN_IF_FAILED(_createShellLink(profile.Name(), profile.GetExpandedIconPath(), args, shLink.put()));
+
+            RETURN_IF_FAILED(jumplistItems->AddObject(shLink.get()));
+        }
+
+        return S_OK;
+    }
+    CATCH_RETURN();
+}
+
+// Method Description:
+// - Creates a ShellLink object. Each item in a jumplist is a ShellLink, which is sort of
+//   like a shortcut. It requires the path to the application (wt.exe), the arguments to pass,
+//   and the path to the icon for the jumplist item. The path to the application isn't passed
+//   into this function, as we'll determine it with GetModuleFileName.
+// Arguments:
+// - name: The name of the item displayed in the jumplist.
+// - path: The path to the icon for the jumplist item.
+// - args: The arguments to pass along with wt.exe
+// - shLink: The shell link object to return.
+// Return Value:
+// - S_OK or HRESULT failure code.
+[[nodiscard]] HRESULT Jumplist::_createShellLink(const std::wstring_view name,
+                                                 const std::wstring_view path,
+                                                 const std::wstring_view args,
+                                                 IShellLinkW** shLink) noexcept
+{
+    try
+    {
+        auto sh = winrt::create_instance<IShellLinkW>(CLSID_ShellLink, CLSCTX_ALL);
+
+        std::filesystem::path module{ wil::GetModuleFileNameW<std::wstring>(nullptr) };
+        RETURN_IF_FAILED(sh->SetPath(module.c_str()));
+        RETURN_IF_FAILED(sh->SetArguments(args.data()));
+
+        PROPVARIANT titleProp;
+        titleProp.vt = VT_LPWSTR;
+        titleProp.pwszVal = const_cast<wchar_t*>(name.data());
+
+        PROPVARIANT iconProp;
+        iconProp.vt = VT_LPWSTR;
+        iconProp.pwszVal = const_cast<wchar_t*>(path.data());
+
+        auto propStore{ sh.as<IPropertyStore>() };
+        RETURN_IF_FAILED(propStore->SetValue(PKEY_Title, titleProp));
+        RETURN_IF_FAILED(propStore->SetValue(PKEY_AppUserModel_DestListLogoUri, iconProp));
+
+        RETURN_IF_FAILED(propStore->Commit());
+
+        *shLink = sh.detach();
+
+        return S_OK;
+    }
+    CATCH_RETURN();
+}
diff --git a/src/cascadia/TerminalApp/Jumplist.h b/src/cascadia/TerminalApp/Jumplist.h
new file mode 100644
index 00000000000..ba3649c0311
--- /dev/null
+++ b/src/cascadia/TerminalApp/Jumplist.h
@@ -0,0 +1,29 @@
+// Copyright (c) Microsoft Corporation.
+// Licensed under the MIT license.
+//
+// Module Name:
+// - Jumplist.h
+//
+// Abstract:
+// - The Jumplist is the menu that pops up when right clicking a pinned
+// item in the taskbar. This class handles updating the Terminal's jumplist
+// using the Terminal's settings.
+//
+
+#pragma once
+
+#include "CascadiaSettings.h"
+#include "Profile.h"
+
+struct IObjectCollection;
+struct IShellLinkW;
+
+class Jumplist
+{
+public:
+    static HRESULT UpdateJumplist(const TerminalApp::CascadiaSettings& settings) noexcept;
+
+private:
+    [[nodiscard]] static HRESULT _updateProfiles(IObjectCollection* jumplistItems, const gsl::span<const winrt::TerminalApp::Profile>& profiles) noexcept;
+    [[nodiscard]] static HRESULT _createShellLink(const std::wstring_view name, const std::wstring_view path, const std::wstring_view args, IShellLinkW** shLink) noexcept;
+};
diff --git a/src/cascadia/TerminalApp/TerminalAppLib.vcxproj b/src/cascadia/TerminalApp/TerminalAppLib.vcxproj
index f4a0ee3c25e..85d3a858790 100644
--- a/src/cascadia/TerminalApp/TerminalAppLib.vcxproj
+++ b/src/cascadia/TerminalApp/TerminalAppLib.vcxproj
@@ -72,6 +72,7 @@
     <ClInclude Include="App.base.h" />
     <ClInclude Include="AppCommandlineArgs.h" />
     <ClInclude Include="Commandline.h" />
+    <ClInclude Include="Jumplist.h" />
     <ClInclude Include="MinMaxCloseControl.h">
       <DependentUpon>MinMaxCloseControl.xaml</DependentUpon>
     </ClInclude>
@@ -155,6 +156,7 @@
     <ClCompile Include="init.cpp" />
     <ClCompile Include="AppCommandlineArgs.cpp" />
     <ClCompile Include="Commandline.cpp" />
+    <ClCompile Include="Jumplist.cpp" />
     <ClCompile Include="MinMaxCloseControl.cpp">
       <DependentUpon>MinMaxCloseControl.xaml</DependentUpon>
     </ClCompile>