diff --git a/src/sql/base/browser/ui/table/media/table.css b/src/sql/base/browser/ui/table/media/table.css
index 903c3621a3..eaff00c275 100644
--- a/src/sql/base/browser/ui/table/media/table.css
+++ b/src/sql/base/browser/ui/table/media/table.css
@@ -101,7 +101,8 @@
 	padding: 4px;
 	z-index: 100000;
 	cursor: default;
-	display: inline-block;
+	display: flex;
+	flex-direction: column;
 	margin: 0;
 	position: absolute;
 }
@@ -118,10 +119,14 @@
 	background: none repeat scroll 0 0 #000000;
 }
 
+.slick-header-menu-image-button-container {
+	flex: 0 0 auto;
+}
+
 .slick-header-menu a.monaco-button.monaco-text-button {
 	width: 60px;
-	margin: 6px 6px 6px 6px;
-	padding: 4px;
+	margin: 5px;
+	padding: 2px;
 }
 
 .slick-header-menu .searchbox-row
@@ -130,6 +135,7 @@
 	align-items: center;
 	padding-left: 5px;
 	margin-top: 5px;
+	flex: 0 0 auto;
 }
 
 .slick-header-menu .searchbox-row .select-all-checkbox
@@ -168,7 +174,6 @@
 {
 	border: 1px solid #BFBDBD;
 	font-size: 8pt;
-	height: 250px;
 	margin-top: 6px;
 	overflow: hidden;
 	padding: 1px;
@@ -176,6 +181,7 @@
 	align-content: flex-start;
 	display: flex;
 	flex-direction: column;
+	flex: 1 1 auto;
 }
 
 .slick-header-menu .filter .filter-option {
@@ -188,6 +194,7 @@
 	display: flex;
 	flex-direction: row;
 	width: 100%;
+	flex: 0 0 auto;
 }
 
 .slick-header-menu .filter-menu-button {
diff --git a/src/sql/base/browser/ui/table/plugins/headerFilter.plugin.ts b/src/sql/base/browser/ui/table/plugins/headerFilter.plugin.ts
index 2aaf372263..e84d7461cf 100644
--- a/src/sql/base/browser/ui/table/plugins/headerFilter.plugin.ts
+++ b/src/sql/base/browser/ui/table/plugins/headerFilter.plugin.ts
@@ -84,6 +84,7 @@ export class HeaderFilter<T extends Slick.SlickData> {
 	private disposableStore = new DisposableStore();
 	private columnButtonMapping: Map<string, HTMLElement> = new Map<string, HTMLElement>();
 	private previouslyFocusedElement: HTMLElement;
+	private listContainer?: HTMLElement;
 
 	constructor(private readonly contextViewProvider: IContextViewProvider, private readonly notificationProvider?: NotificationProvider, private readonly options: ITableFilterOptions = DefaultTableFilterOptions) {
 	}
@@ -180,7 +181,7 @@ export class HeaderFilter<T extends Slick.SlickData> {
 	}
 
 	private createButtonMenuItem(title: string, command: HeaderFilterCommands, iconClass: string): Button {
-		const buttonContainer = append(this.menu, $(''));
+		const buttonContainer = append(this.menu, $('.slick-header-menu-image-button-container'));
 		const button = new Button(buttonContainer);
 		button.icon = { id: `slick-header-menuicon ${iconClass}` };
 		button.label = title;
@@ -278,8 +279,8 @@ export class HeaderFilter<T extends Slick.SlickData> {
 
 		this.filteredListData = this.listData;
 
-		const filter = append(this.menu, $('.filter'));
-		this.list = new List<TableFilterListElement>('TableFilter', filter, new TableFilterListDelegate(), [new TableFilterListRenderer()], {
+		this.listContainer = append(this.menu, $('.filter'));
+		this.list = new List<TableFilterListElement>('TableFilter', this.listContainer, new TableFilterListDelegate(), [new TableFilterListRenderer()], {
 			multipleSelectionSupport: false,
 			keyboardSupport: true,
 			mouseSupport: true,
@@ -347,29 +348,26 @@ export class HeaderFilter<T extends Slick.SlickData> {
 		}
 		this.previouslyFocusedElement = document.activeElement as HTMLElement;
 		await this.createFilterMenu(filterButton);
-		// Get the absolute coordinates of the filter button
-		const offset = jQuery(filterButton).offset();
-		// Calculate the position of menu item
-		let menuleft = offset.left - this.menu.offsetWidth + filterButton.offsetWidth;
-		let menutop = offset.top + filterButton.offsetHeight;
-		// Make sure the entire menu is on screen.
-		// If there is not enough vertical space under the filter button, we will move up the menu.
-		// If the left of the menu is off screen (negative value), we will show the menu next to the left edge of window.
+		// Try to fit the menu in the screen.
 		// We don't really consider the case when there is not enough space to show the entire menu since in that case the application is not usable already.
-		if (menutop + this.menu.offsetHeight > window.innerHeight) {
-			menutop = window.innerHeight - this.menu.offsetHeight;
-		}
-		menuleft = menuleft > 0 ? menuleft : 0;
+
+		const offset = jQuery(filterButton).offset();
+		// If there is not enough vertical space under the filter button, we will move up the menu.
+		const menuTop = offset.top + this.menu.offsetHeight <= window.innerHeight ? offset.top : window.innerHeight - this.menu.offsetHeight;
+		// Make sure the menu is on the screen horizontally.
+		const menuLeft = offset.left + filterButton.offsetWidth + this.menu.offsetWidth <= window.innerWidth ? offset.left + filterButton.offsetWidth : window.innerWidth - this.menu.offsetWidth;
 
 		this.contextViewProvider.showContextView({
 			getAnchor: () => {
 				return {
-					x: menuleft,
-					y: menutop
+					x: menuLeft,
+					y: menuTop
 				};
 			},
 			render: (container: HTMLElement) => {
 				container.appendChild(this.menu);
+				// Set the list size to its container size so that scrolling works correctly..
+				this.list.layout(this.listContainer.clientHeight);
 				return {
 					dispose: () => {
 						this.disposeMenu();
@@ -401,6 +399,11 @@ export class HeaderFilter<T extends Slick.SlickData> {
 		// first add it to the document so that we can get the actual size of the menu
 		// later, it will be added to the correct container
 		this.menu = append(document.body, $('.slick-header-menu'));
+		const MenuVerticalPadding = 10;
+		const MenuBarHeight = 30;
+		const DefaultMenuHeight = 350;
+		// Make sure the menu can fit in the screen.
+		this.menu.style.height = `${Math.min(DefaultMenuHeight, window.innerHeight - MenuBarHeight) - MenuVerticalPadding}px`;
 
 		this.sortAscButton = this.createButtonMenuItem(localize('table.sortAscending', "Sort Ascending"), 'sort-asc', 'ascending');
 		this.sortDescButton = this.createButtonMenuItem(localize('table.sortDescending', "Sort Descending"), 'sort-desc', 'descending');