diff --git a/Mac/Base.lproj/MainWindow.storyboard b/Mac/Base.lproj/MainWindow.storyboard
index 57f6d53b4..c83f3b86b 100644
--- a/Mac/Base.lproj/MainWindow.storyboard
+++ b/Mac/Base.lproj/MainWindow.storyboard
@@ -1,7 +1,8 @@
 <?xml version="1.0" encoding="UTF-8"?>
-<document type="com.apple.InterfaceBuilder3.Cocoa.Storyboard.XIB" version="3.0" toolsVersion="16096" targetRuntime="MacOSX.Cocoa" propertyAccessControl="none" useAutolayout="YES" initialViewController="B8D-0N-5wS">
+<document type="com.apple.InterfaceBuilder3.Cocoa.Storyboard.XIB" version="3.0" toolsVersion="17132" targetRuntime="MacOSX.Cocoa" propertyAccessControl="none" useAutolayout="YES" initialViewController="B8D-0N-5wS">
     <dependencies>
-        <plugIn identifier="com.apple.InterfaceBuilder.CocoaPlugin" version="16096"/>
+        <deployment identifier="macosx"/>
+        <plugIn identifier="com.apple.InterfaceBuilder.CocoaPlugin" version="17132"/>
         <capability name="documents saved in the Xcode 8 format" minToolsVersion="8.0"/>
     </dependencies>
     <scenes>
@@ -185,7 +186,7 @@
                                 <toolbarItem implicitItemIdentifier="ACB5604B-4543-4985-BA1A-54ADA9DF5845" label="Clean UP" paletteLabel="Clean Up" toolTip="Clean Up" image="cleanUp" sizingBehavior="auto" id="SsT-iS-pKE" customClass="RSToolbarItem" customModule="RSCore">
                                     <button key="view" verticalHuggingPriority="750" id="9At-yP-WNY">
                                         <rect key="frame" x="7" y="14" width="42" height="25"/>
-                                        <autoresizingMask key="autoresizingMask" flexibleMaxX="YES" flexibleMinY="YES"/>
+                                        <autoresizingMask key="autoresizingMask"/>
                                         <buttonCell key="cell" type="roundTextured" bezelStyle="texturedRounded" image="cleanUp" imagePosition="only" alignment="center" lineBreakMode="truncatingTail" state="on" borderStyle="border" imageScaling="proportionallyDown" inset="2" id="Zwg-74-ZkZ">
                                             <behavior key="behavior" pushIn="YES" lightByBackground="YES" lightByGray="YES"/>
                                             <font key="font" metaFont="system"/>
@@ -318,16 +319,16 @@
                                 <rect key="frame" x="0.0" y="0.0" width="166" height="283"/>
                                 <clipView key="contentView" drawsBackground="NO" copiesOnScroll="NO" id="2eU-Wz-F9g">
                                     <rect key="frame" x="0.0" y="0.0" width="166" height="283"/>
-                                    <autoresizingMask key="autoresizingMask"/>
+                                    <autoresizingMask key="autoresizingMask" widthSizable="YES" heightSizable="YES"/>
                                     <subviews>
                                         <outlineView verticalHuggingPriority="750" allowsExpansionToolTips="YES" columnAutoresizingStyle="firstColumnOnly" selectionHighlightStyle="sourceList" columnReordering="NO" columnResizing="NO" autosaveColumns="NO" typeSelect="NO" rowHeight="26" viewBased="YES" floatsGroupRows="NO" indentationPerLevel="23" outlineTableColumn="ih9-mJ-EA7" id="cnV-kg-Dn2" customClass="SidebarOutlineView" customModule="NetNewsWire" customModuleProvider="target">
-                                            <rect key="frame" x="0.0" y="0.0" width="167" height="283"/>
+                                            <rect key="frame" x="0.0" y="0.0" width="166" height="283"/>
                                             <autoresizingMask key="autoresizingMask" widthSizable="YES" heightSizable="YES"/>
                                             <size key="intercellSpacing" width="3" height="0.0"/>
                                             <color key="backgroundColor" name="_sourceListBackgroundColor" catalog="System" colorSpace="catalog"/>
                                             <color key="gridColor" name="gridColor" catalog="System" colorSpace="catalog"/>
                                             <tableColumns>
-                                                <tableColumn width="164" minWidth="23" maxWidth="1000" id="ih9-mJ-EA7">
+                                                <tableColumn width="134" minWidth="23" maxWidth="1000" id="ih9-mJ-EA7">
                                                     <tableHeaderCell key="headerCell" lineBreakMode="truncatingTail" borderStyle="border">
                                                         <color key="textColor" name="headerTextColor" catalog="System" colorSpace="catalog"/>
                                                         <color key="backgroundColor" name="headerColor" catalog="System" colorSpace="catalog"/>
@@ -340,7 +341,7 @@
                                                     <tableColumnResizingMask key="resizingMask" resizeWithTable="YES"/>
                                                     <prototypeCellViews>
                                                         <tableCellView identifier="HeaderCell" id="qkt-WA-5tB">
-                                                            <rect key="frame" x="1" y="0.0" width="164" height="17"/>
+                                                            <rect key="frame" x="11" y="0.0" width="143" height="17"/>
                                                             <autoresizingMask key="autoresizingMask" widthSizable="YES" heightSizable="YES"/>
                                                             <subviews>
                                                                 <textField verticalHuggingPriority="750" fixedFrame="YES" translatesAutoresizingMaskIntoConstraints="NO" id="fNJ-z1-0Up">
@@ -358,7 +359,7 @@
                                                             </connections>
                                                         </tableCellView>
                                                         <tableCellView identifier="DataCell" id="HJn-Tm-YNO" customClass="SidebarCell" customModule="NetNewsWire" customModuleProvider="target">
-                                                            <rect key="frame" x="1" y="17" width="164" height="17"/>
+                                                            <rect key="frame" x="11" y="17" width="143" height="17"/>
                                                             <autoresizingMask key="autoresizingMask" widthSizable="YES" heightSizable="YES"/>
                                                         </tableCellView>
                                                     </prototypeCellViews>
@@ -616,9 +617,9 @@
         </scene>
     </scenes>
     <resources>
-        <image name="NSAddTemplate" width="11" height="11"/>
-        <image name="NSRefreshTemplate" width="11" height="15"/>
-        <image name="NSShareTemplate" width="11" height="16"/>
+        <image name="NSAddTemplate" width="15" height="11"/>
+        <image name="NSRefreshTemplate" width="14" height="14"/>
+        <image name="NSShareTemplate" width="16" height="15"/>
         <image name="cleanUp" width="149" height="113"/>
         <image name="filterInactive" width="100" height="101"/>
         <image name="markAllRead" width="22" height="19"/>
diff --git a/Multiplatform/Shared/AppAssets.swift b/Multiplatform/Shared/AppAssets.swift
index e680fbafc..3243d65f9 100644
--- a/Multiplatform/Shared/AppAssets.swift
+++ b/Multiplatform/Shared/AppAssets.swift
@@ -70,6 +70,10 @@ struct AppAssets {
 		return Image("ArticleExtractorOn")
 	}()
 
+	static var checkmarkImage: Image = {
+		return Image(systemName: "checkmark")
+	}()
+	
 	static var copyImage: Image = {
 		return Image(systemName: "doc.on.doc")
 	}()
diff --git a/Multiplatform/Shared/AppDefaults.swift b/Multiplatform/Shared/AppDefaults.swift
index 52452c851..a86edcad0 100644
--- a/Multiplatform/Shared/AppDefaults.swift
+++ b/Multiplatform/Shared/AppDefaults.swift
@@ -170,7 +170,11 @@ final class AppDefaults: ObservableObject {
 	}
 	
 	// MARK: Timeline
-	@AppStorage(wrappedValue: false, Key.timelineGroupByFeed, store: store) var timelineGroupByFeed: Bool
+	@AppStorage(wrappedValue: false, Key.timelineGroupByFeed, store: store) var timelineGroupByFeed: Bool {
+		didSet {
+			objectWillChange.send()
+		}
+	}
 	
 	@AppStorage(wrappedValue: 2.0, Key.timelineNumberOfLines, store: store) var timelineNumberOfLines: Double {
 		didSet {
@@ -185,7 +189,11 @@ final class AppDefaults: ObservableObject {
 	}
 	
 	/// Set to `true` to sort oldest to newest, `false` for newest to oldest. Default is `false`.
-	@AppStorage(wrappedValue: false, Key.timelineSortDirection, store: store) var timelineSortDirection: Bool
+	@AppStorage(wrappedValue: false, Key.timelineSortDirection, store: store) var timelineSortDirection: Bool {
+		didSet {
+			objectWillChange.send()
+		}
+	}
 	
 	// MARK: Refresh
 	@AppStorage(wrappedValue: false, Key.refreshClearsReadArticles, store: store) var refreshClearsReadArticles: Bool
diff --git a/Multiplatform/Shared/Timeline/TimelineModel.swift b/Multiplatform/Shared/Timeline/TimelineModel.swift
index 9ada23d49..fd81f0ab1 100644
--- a/Multiplatform/Shared/Timeline/TimelineModel.swift
+++ b/Multiplatform/Shared/Timeline/TimelineModel.swift
@@ -55,25 +55,18 @@ class TimelineModel: ObservableObject, UndoableCommandRunner {
 		return _idToArticleDictionary
 	}
 
-	private var sortDirection = AppDefaults.shared.timelineSortDirection {
-		didSet {
-			if sortDirection != oldValue {
-				sortParametersDidChange()
-			}
-		}
+	private var sortDirection: Bool {
+		AppDefaults.shared.timelineSortDirection
 	}
 	
-	private var groupByFeed = AppDefaults.shared.timelineGroupByFeed {
-		didSet {
-			if groupByFeed != oldValue {
-				sortParametersDidChange()
-			}
-		}
+	private var groupByFeed: Bool {
+		AppDefaults.shared.timelineGroupByFeed
 	}
 	
 	init() {
 		NotificationCenter.default.addObserver(self, selector: #selector(statusesDidChange(_:)), name: .StatusesDidChange, object: nil)
-
+		NotificationCenter.default.addObserver(self, selector: #selector(userDefaultsDidChange(_:)), name: UserDefaults.didChangeNotification, object: nil)
+		
 		// TODO: This should be rewritten to use Combine correctly
 		selectedArticleIDsCancellable = $selectedArticleIDs.sink { [weak self] articleIDs in
 			guard let self = self else { return }
@@ -213,6 +206,13 @@ private extension TimelineModel {
 		}
 	}
 	
+	@objc func userDefaultsDidChange(_ note: Notification) {
+		performBlockAndRestoreSelection {
+			articles = articles.sortedByDate(sortDirection ? .orderedDescending : .orderedAscending, groupByFeed: groupByFeed)
+			rebuildTimelineItems()
+		}
+	}
+	
 	// MARK: Timeline Management
 	
 	func resetReadFilter() {
@@ -233,13 +233,6 @@ private extension TimelineModel {
 		}
 	}
 
-	func sortParametersDidChange() {
-		performBlockAndRestoreSelection {
-			let unsortedArticles = Set(articles)
-			replaceArticles(with: unsortedArticles)
-		}
-	}
-	
 	func performBlockAndRestoreSelection(_ block: (() -> Void)) {
 //		let savedSelection = selectedArticleIDs()
 		block()
diff --git a/Multiplatform/Shared/Timeline/TimelineSortOrderView.swift b/Multiplatform/Shared/Timeline/TimelineSortOrderView.swift
new file mode 100644
index 000000000..eb5034da6
--- /dev/null
+++ b/Multiplatform/Shared/Timeline/TimelineSortOrderView.swift
@@ -0,0 +1,64 @@
+//
+//  TimelineSortOrderView.swift
+//  Multiplatform macOS
+//
+//  Created by Maurice Parker on 7/12/20.
+//  Copyright © 2020 Ranchero Software. All rights reserved.
+//
+
+import SwiftUI
+
+struct TimelineSortOrderView: View {
+	
+	@EnvironmentObject var settings: AppDefaults
+	@State var selection: Int = 1
+	
+	var body: some View {
+		Menu {
+			Button {
+				settings.timelineSortDirection = true
+			} label: {
+				HStack {
+					Text("Newest to Oldest")
+					if settings.timelineSortDirection {
+						Spacer()
+						AppAssets.checkmarkImage
+					}
+				}
+			}
+			Button {
+				settings.timelineSortDirection = false
+			} label: {
+				HStack {
+					Text("Oldest to Newest")
+					if !settings.timelineSortDirection {
+						Spacer()
+						AppAssets.checkmarkImage
+					}
+				}
+			}
+			Divider()
+			Button {
+				settings.timelineGroupByFeed.toggle()
+			} label: {
+				HStack {
+					Text("Group by Feed")
+					if settings.timelineGroupByFeed {
+						Spacer()
+						AppAssets.checkmarkImage
+					}
+				}
+			}
+		} label : {
+			if settings.timelineSortDirection {
+				Text("Sort Newest to Oldest")
+			} else {
+				Text("Sort Oldest to Newest")
+			}
+		}
+		.font(.subheadline)
+		.frame(width: 150)
+		.padding(.top, 8).padding(.leading)
+		.menuStyle(BorderlessButtonMenuStyle())
+	}
+}
diff --git a/Multiplatform/Shared/Timeline/TimelineView.swift b/Multiplatform/Shared/Timeline/TimelineView.swift
index 7a18895b9..8b30e55de 100644
--- a/Multiplatform/Shared/Timeline/TimelineView.swift
+++ b/Multiplatform/Shared/Timeline/TimelineView.swift
@@ -17,6 +17,7 @@ struct TimelineView: View {
 		#if os(macOS)
 		VStack {
 			HStack {
+				TimelineSortOrderView()
 				Spacer()
 				Button (action: {
 					withAnimation {
diff --git a/NetNewsWire.xcodeproj/project.pbxproj b/NetNewsWire.xcodeproj/project.pbxproj
index 08d514817..3c358c416 100644
--- a/NetNewsWire.xcodeproj/project.pbxproj
+++ b/NetNewsWire.xcodeproj/project.pbxproj
@@ -298,6 +298,7 @@
 		5193CD5A245E44A90092735E /* RedditFeedProvider-Extensions.swift in Sources */ = {isa = PBXBuildFile; fileRef = 5193CD57245E44A90092735E /* RedditFeedProvider-Extensions.swift */; };
 		5194736E24BBB937001A2939 /* HiddenModifier.swift in Sources */ = {isa = PBXBuildFile; fileRef = 5194736D24BBB937001A2939 /* HiddenModifier.swift */; };
 		5194736F24BBB937001A2939 /* HiddenModifier.swift in Sources */ = {isa = PBXBuildFile; fileRef = 5194736D24BBB937001A2939 /* HiddenModifier.swift */; };
+		5194737124BBCAF4001A2939 /* TimelineSortOrderView.swift in Sources */ = {isa = PBXBuildFile; fileRef = 5194737024BBCAF4001A2939 /* TimelineSortOrderView.swift */; };
 		519B8D332143397200FA689C /* SharingServiceDelegate.swift in Sources */ = {isa = PBXBuildFile; fileRef = 519B8D322143397200FA689C /* SharingServiceDelegate.swift */; };
 		519E743D22C663F900A78E47 /* SceneDelegate.swift in Sources */ = {isa = PBXBuildFile; fileRef = 519E743422C663F900A78E47 /* SceneDelegate.swift */; };
 		519ED456244828C3007F8E94 /* AddExtensionPointViewController.swift in Sources */ = {isa = PBXBuildFile; fileRef = 519ED455244828C3007F8E94 /* AddExtensionPointViewController.swift */; };
@@ -1963,6 +1964,7 @@
 		51938DF1231AFC660055A1A0 /* SearchTimelineFeedDelegate.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = SearchTimelineFeedDelegate.swift; sourceTree = "<group>"; };
 		5193CD57245E44A90092735E /* RedditFeedProvider-Extensions.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = "RedditFeedProvider-Extensions.swift"; sourceTree = "<group>"; };
 		5194736D24BBB937001A2939 /* HiddenModifier.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = HiddenModifier.swift; sourceTree = "<group>"; };
+		5194737024BBCAF4001A2939 /* TimelineSortOrderView.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = TimelineSortOrderView.swift; sourceTree = "<group>"; };
 		519B8D322143397200FA689C /* SharingServiceDelegate.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = SharingServiceDelegate.swift; sourceTree = "<group>"; };
 		519E743422C663F900A78E47 /* SceneDelegate.swift */ = {isa = PBXFileReference; fileEncoding = 4; lastKnownFileType = sourcecode.swift; path = SceneDelegate.swift; sourceTree = "<group>"; };
 		519ED455244828C3007F8E94 /* AddExtensionPointViewController.swift */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.swift; path = AddExtensionPointViewController.swift; sourceTree = "<group>"; };
@@ -2833,13 +2835,14 @@
 		51919FCB24AB855000541E64 /* Timeline */ = {
 			isa = PBXGroup;
 			children = (
-				5177470224B2657F00EB0F74 /* TimelineToolbarModifier.swift */,
 				51919FED24AB85E400541E64 /* TimelineContainerView.swift */,
 				51919FF324AB869C00541E64 /* TimelineItem.swift */,
 				514E6C0124AD29A300AC6F6E /* TimelineItemStatusView.swift */,
 				514E6BD924ACEA0400AC6F6E /* TimelineItemView.swift */,
 				51919FF024AB864A00541E64 /* TimelineModel.swift */,
+				5194737024BBCAF4001A2939 /* TimelineSortOrderView.swift */,
 				517B2EEA24B40E09001AC46C /* TimelineTitleModifier.swift */,
+				5177470224B2657F00EB0F74 /* TimelineToolbarModifier.swift */,
 				51919FF624AB8B7700541E64 /* TimelineView.swift */,
 			);
 			path = Timeline;
@@ -5200,6 +5203,7 @@
 				514E6BDB24ACEA0400AC6F6E /* TimelineItemView.swift in Sources */,
 				51E4996E24A8764C00B667CB /* ActivityManager.swift in Sources */,
 				51E4995A24A873F900B667CB /* ErrorHandler.swift in Sources */,
+				5194737124BBCAF4001A2939 /* TimelineSortOrderView.swift in Sources */,
 				51E4991F24A8094300B667CB /* RSImage-AppIcons.swift in Sources */,
 				51A5769724AE617200078888 /* ArticleContainerView.swift in Sources */,
 				51E4991224A808FB00B667CB /* AddWebFeedDefaultContainer.swift in Sources */,