diff --git a/frontend/app/element/tooltip.tsx b/frontend/app/element/tooltip.tsx
index c15b85060e..d49606c42a 100644
--- a/frontend/app/element/tooltip.tsx
+++ b/frontend/app/element/tooltip.tsx
@@ -1,6 +1,7 @@
 // Copyright 2025, Command Line Inc.
 // SPDX-License-Identifier: Apache-2.0
 
+import { cn } from "@/util/util";
 import {
     FloatingPortal,
     autoUpdate,
@@ -11,7 +12,6 @@ import {
     useHover,
     useInteractions,
 } from "@floating-ui/react";
-import { cn } from "@/util/util";
 import { useEffect, useRef, useState } from "react";
 
 interface TooltipProps {
@@ -19,12 +19,13 @@ interface TooltipProps {
     content: React.ReactNode;
     placement?: "top" | "bottom" | "left" | "right";
     forceOpen?: boolean;
+    disable?: boolean;
     divClassName?: string;
     divStyle?: React.CSSProperties;
     divOnClick?: (e: React.MouseEvent<HTMLDivElement>) => void;
 }
 
-export function Tooltip({
+function TooltipInner({
     children,
     content,
     placement = "top",
@@ -32,7 +33,7 @@ export function Tooltip({
     divClassName,
     divStyle,
     divOnClick,
-}: TooltipProps) {
+}: Omit<TooltipProps, 'disable'>) {
     const [isOpen, setIsOpen] = useState(forceOpen);
     const [isVisible, setIsVisible] = useState(false);
     const timeoutRef = useRef<number | null>(null);
@@ -63,11 +64,7 @@ export function Tooltip({
             }
         },
         placement,
-        middleware: [
-            offset(10),
-            flip(),
-            shift({ padding: 12 }),
-        ],
+        middleware: [offset(10), flip(), shift({ padding: 12 })],
         whileElementsMounted: autoUpdate,
     });
 
@@ -132,7 +129,7 @@ export function Tooltip({
                         }}
                         {...getFloatingProps()}
                         className={cn(
-                            "bg-white dark:bg-panel border border-border rounded-md px-2 py-1 text-xs text-foreground shadow-xl z-50"
+                            "bg-gray-800 border border-border rounded-md px-2 py-1 text-xs text-foreground shadow-xl z-50"
                         )}
                     >
                         {content}
@@ -141,4 +138,39 @@ export function Tooltip({
             )}
         </>
     );
-}
\ No newline at end of file
+}
+
+export function Tooltip({
+    children,
+    content,
+    placement = "top",
+    forceOpen = false,
+    disable = false,
+    divClassName,
+    divStyle,
+    divOnClick,
+}: TooltipProps) {
+    if (disable) {
+        return (
+            <div
+                className={divClassName}
+                style={divStyle}
+                onClick={divOnClick}
+            >
+                {children}
+            </div>
+        );
+    }
+
+    return (
+        <TooltipInner
+            children={children}
+            content={content}
+            placement={placement}
+            forceOpen={forceOpen}
+            divClassName={divClassName}
+            divStyle={divStyle}
+            divOnClick={divOnClick}
+        />
+    );
+}
diff --git a/frontend/app/notification/notificationpopover.scss b/frontend/app/notification/notificationpopover.scss
deleted file mode 100644
index 6a3b983f0c..0000000000
--- a/frontend/app/notification/notificationpopover.scss
+++ /dev/null
@@ -1,64 +0,0 @@
-// Copyright 2024, Command Line Inc.
-// SPDX-License-Identifier: Apache-2.0
-
-.notification-popover {
-    padding: 8px 2px 8px 0px;
-    display: flex;
-    align-items: center;
-    justify-content: center;
-
-    button {
-        width: 27px;
-        height: 26px;
-        display: flex;
-        justify-content: center;
-
-        i {
-            font-size: 17px;
-        }
-    }
-}
-
-.notification-content {
-    display: flex;
-    width: 380px;
-    padding: 10px 0 0;
-    flex-direction: column;
-    align-items: flex-start;
-    column-gap: 8px;
-    border-radius: 8px;
-    border: 0.5px solid rgba(255, 255, 255, 0.12);
-    background: #232323;
-    box-shadow: 0px 8px 32px 0px rgba(0, 0, 0, 0.25);
-
-    .divider {
-        background: rgba(255, 255, 255, 0.08);
-        height: 1px;
-        width: 100%;
-    }
-
-    .header {
-        display: flex;
-        align-items: center;
-        justify-content: space-between;
-        width: 100%;
-        padding: 0 10px 8px 10px;
-        border-bottom: 1px solid rgba(255, 255, 255, 0.08);
-
-        span {
-            color: var(--main-text-color);
-            font-size: 14px;
-            font-style: normal;
-            font-weight: 600;
-            line-height: 16px;
-        }
-    }
-
-    .close-all-btn {
-        font-size: 13px;
-        font-style: normal;
-        font-weight: 400;
-        line-height: 16px;
-        color: rgba(255, 255, 255, 0.4);
-    }
-}
diff --git a/frontend/app/notification/notificationpopover.tsx b/frontend/app/notification/notificationpopover.tsx
index 70596852eb..471ef0fafd 100644
--- a/frontend/app/notification/notificationpopover.tsx
+++ b/frontend/app/notification/notificationpopover.tsx
@@ -13,8 +13,6 @@ import { NotificationItem } from "./notificationitem";
 import { useUpdateNotifier } from "./updatenotifier";
 import { useNotification } from "./usenotification";
 
-import "./notificationpopover.scss";
-
 const NotificationPopover = () => {
     useUpdateNotifier();
     const {
@@ -51,14 +49,14 @@ const NotificationPopover = () => {
 
     return (
         <Popover
-            className="notification-popover"
+            className="w-full pb-2 pt-1 pl-0 pr-0.5 flex items-center justify-center"
             placement="left-end"
             offset={{ mainAxis: 20, crossAxis: 2 }}
             onDismiss={handleTogglePopover}
         >
             <PopoverButton
                 className={clsx(
-                    "notification-trigger-button horizontal-padding-6 vertical-padding-4 border-radius-",
+                    "w-[27px] h-[26px] flex justify-center [&>i]:text-[17px] horizontal-padding-6 vertical-padding-4 border-radius-",
                     addOnClassNames
                 )}
                 disabled={notifications.length === 0}
@@ -67,11 +65,11 @@ const NotificationPopover = () => {
                 {getIcon()}
             </PopoverButton>
             {notifications.length > 0 && (
-                <PopoverContent className="notification-content">
-                    <div className="header">
-                        <span>Notifications</span>
+                <PopoverContent className="flex w-[380px] pt-2.5 pb-0 px-0 flex-col items-start gap-x-2 rounded-lg border-[0.5px] border-white/12 bg-[#232323] shadow-[0px_8px_32px_0px_rgba(0,0,0,0.25)]">
+                    <div className="flex items-center justify-between w-full px-2.5 pb-2 border-b border-white/8">
+                        <span className="text-foreground text-sm font-semibold leading-4">Notifications</span>
                         <Button
-                            className="ghost grey close-all-btn horizontal-padding-3 vertical-padding-3"
+                            className="ghost grey text-[13px] font-normal leading-4 text-white/40 horizontal-padding-3 vertical-padding-3"
                             onClick={(e) => {
                                 e.stopPropagation();
                                 removeAllNotifications();
@@ -98,7 +96,7 @@ const NotificationPopover = () => {
                                     onMouseEnter={() => setHoveredId(notif.id)}
                                     onMouseLeave={() => setHoveredId(null)}
                                 />
-                                {index !== notifications.length - 1 && <div className="divider"></div>}
+                                {index !== notifications.length - 1 && <div className="bg-white/8 h-px w-full"></div>}
                             </Fragment>
                         ))}
                     </OverlayScrollbarsComponent>
diff --git a/frontend/app/workspace/widgets.tsx b/frontend/app/workspace/widgets.tsx
new file mode 100644
index 0000000000..6bfc518df8
--- /dev/null
+++ b/frontend/app/workspace/widgets.tsx
@@ -0,0 +1,243 @@
+// Copyright 2025, Command Line Inc.
+// SPDX-License-Identifier: Apache-2.0
+
+import { Tooltip } from "@/app/element/tooltip";
+import { NotificationPopover } from "@/app/notification/notificationpopover";
+import { ContextMenuModel } from "@/app/store/contextmenu";
+import { RpcApi } from "@/app/store/wshclientapi";
+import { TabRpcClient } from "@/app/store/wshrpcutil";
+import { atoms, createBlock, getApi, isDev } from "@/store/global";
+import { fireAndForget, isBlank, makeIconClass } from "@/util/util";
+import clsx from "clsx";
+import { useAtomValue } from "jotai";
+import { memo, useCallback, useEffect, useRef, useState } from "react";
+
+function sortByDisplayOrder(wmap: { [key: string]: WidgetConfigType }): WidgetConfigType[] {
+    if (wmap == null) {
+        return [];
+    }
+    const wlist = Object.values(wmap);
+    wlist.sort((a, b) => {
+        return (a["display:order"] ?? 0) - (b["display:order"] ?? 0);
+    });
+    return wlist;
+}
+
+async function handleWidgetSelect(widget: WidgetConfigType) {
+    const blockDef = widget.blockdef;
+    createBlock(blockDef, widget.magnified);
+}
+
+const Widget = memo(({ widget, mode }: { widget: WidgetConfigType; mode: "normal" | "compact" | "supercompact" }) => {
+    const [isTruncated, setIsTruncated] = useState(false);
+    const labelRef = useRef<HTMLDivElement>(null);
+
+    useEffect(() => {
+        if (mode === "normal" && labelRef.current) {
+            const element = labelRef.current;
+            setIsTruncated(element.scrollWidth > element.clientWidth);
+        }
+    }, [mode, widget.label]);
+
+    const shouldDisableTooltip = mode !== "normal" ? false : !isTruncated;
+
+    return (
+        <Tooltip
+            content={widget.description || widget.label}
+            placement="left"
+            disable={shouldDisableTooltip}
+            divClassName={clsx(
+                "flex flex-col justify-center items-center w-full py-1.5 pr-0.5 text-secondary overflow-hidden rounded-sm hover:bg-hoverbg hover:text-white cursor-pointer",
+                mode === "supercompact" ? "text-sm" : "text-lg",
+                widget["display:hidden"] && "hidden"
+            )}
+            divOnClick={() => handleWidgetSelect(widget)}
+        >
+            <div style={{ color: widget.color }}>
+                <i className={makeIconClass(widget.icon, true, { defaultIcon: "browser" })}></i>
+            </div>
+            {mode === "normal" && !isBlank(widget.label) ? (
+                <div
+                    ref={labelRef}
+                    className="text-xxs mt-0.5 w-full px-0.5 text-center whitespace-nowrap overflow-hidden text-ellipsis"
+                >
+                    {widget.label}
+                </div>
+            ) : null}
+        </Tooltip>
+    );
+});
+
+const Widgets = memo(() => {
+    const fullConfig = useAtomValue(atoms.fullConfigAtom);
+    const [mode, setMode] = useState<"normal" | "compact" | "supercompact">("normal");
+    const containerRef = useRef<HTMLDivElement>(null);
+    const measurementRef = useRef<HTMLDivElement>(null);
+
+    const helpWidget: WidgetConfigType = {
+        icon: "circle-question",
+        label: "help",
+        blockdef: {
+            meta: {
+                view: "help",
+            },
+        },
+    };
+    const tipsWidget: WidgetConfigType = {
+        icon: "lightbulb",
+        label: "tips",
+        blockdef: {
+            meta: {
+                view: "tips",
+            },
+        },
+    };
+    const showHelp = fullConfig?.settings?.["widget:showhelp"] ?? true;
+    const widgets = sortByDisplayOrder(fullConfig?.widgets);
+
+    const checkModeNeeded = useCallback(() => {
+        if (!containerRef.current || !measurementRef.current) return;
+
+        const containerHeight = containerRef.current.clientHeight;
+        const normalHeight = measurementRef.current.scrollHeight;
+        const gracePeriod = 10;
+
+        let newMode: "normal" | "compact" | "supercompact" = "normal";
+
+        if (normalHeight > containerHeight - gracePeriod) {
+            newMode = "compact";
+            
+            // Calculate total widget count for supercompact check
+            const totalWidgets = (widgets?.length || 0) + (showHelp ? 2 : 0);
+            const minHeightPerWidget = 32;
+            const requiredHeight = totalWidgets * minHeightPerWidget;
+            
+            if (requiredHeight > containerHeight) {
+                newMode = "supercompact";
+            }
+        }
+
+        if (newMode !== mode) {
+            setMode(newMode);
+        }
+    }, [mode, widgets, showHelp]);
+
+    useEffect(() => {
+        const resizeObserver = new ResizeObserver(() => {
+            checkModeNeeded();
+        });
+
+        if (containerRef.current) {
+            resizeObserver.observe(containerRef.current);
+        }
+
+        return () => {
+            resizeObserver.disconnect();
+        };
+    }, [checkModeNeeded]);
+
+    useEffect(() => {
+        checkModeNeeded();
+    }, [widgets, showHelp, checkModeNeeded]);
+
+    const handleWidgetsBarContextMenu = (e: React.MouseEvent) => {
+        e.preventDefault();
+        const menu: ContextMenuItem[] = [
+            {
+                label: "Edit widgets.json",
+                click: () => {
+                    fireAndForget(async () => {
+                        const path = `${getApi().getConfigDir()}/widgets.json`;
+                        const blockDef: BlockDef = {
+                            meta: { view: "preview", file: path },
+                        };
+                        await createBlock(blockDef, false, true);
+                    });
+                },
+            },
+            {
+                label: "Show Help Widgets",
+                submenu: [
+                    {
+                        label: "On",
+                        type: "checkbox",
+                        checked: showHelp,
+                        click: () => {
+                            fireAndForget(async () => {
+                                await RpcApi.SetConfigCommand(TabRpcClient, { "widget:showhelp": true });
+                            });
+                        },
+                    },
+                    {
+                        label: "Off",
+                        type: "checkbox",
+                        checked: !showHelp,
+                        click: () => {
+                            fireAndForget(async () => {
+                                await RpcApi.SetConfigCommand(TabRpcClient, { "widget:showhelp": false });
+                            });
+                        },
+                    },
+                ],
+            },
+        ];
+        ContextMenuModel.showContextMenu(menu, e);
+    };
+
+    return (
+        <>
+            <div
+                ref={containerRef}
+                className="flex flex-col w-12 overflow-hidden py-1 -ml-1 select-none"
+                onContextMenu={handleWidgetsBarContextMenu}
+            >
+                {mode === "supercompact" ? (
+                    <>
+                        <div className="grid grid-cols-2 gap-0 w-full">
+                            {widgets?.map((data, idx) => <Widget key={`widget-${idx}`} widget={data} mode={mode} />)}
+                        </div>
+                        <div className="flex-grow" />
+                        {showHelp ? (
+                            <div className="grid grid-cols-2 gap-0 w-full">
+                                <Widget key="tips" widget={tipsWidget} mode={mode} />
+                                <Widget key="help" widget={helpWidget} mode={mode} />
+                            </div>
+                        ) : null}
+                    </>
+                ) : (
+                    <>
+                        {widgets?.map((data, idx) => <Widget key={`widget-${idx}`} widget={data} mode={mode} />)}
+                        <div className="flex-grow" />
+                        {showHelp ? (
+                            <>
+                                <Widget key="tips" widget={tipsWidget} mode={mode} />
+                                <Widget key="help" widget={helpWidget} mode={mode} />
+                            </>
+                        ) : null}
+                    </>
+                )}
+                {isDev() ? <NotificationPopover /> : null}
+            </div>
+
+            <div
+                ref={measurementRef}
+                className="flex flex-col w-12 py-1 -ml-1 select-none absolute -z-10 opacity-0 pointer-events-none"
+            >
+                {widgets?.map((data, idx) => (
+                    <Widget key={`measurement-widget-${idx}`} widget={data} mode="normal" />
+                ))}
+                <div className="flex-grow" />
+                {showHelp ? (
+                    <>
+                        <Widget key="measurement-tips" widget={tipsWidget} mode="normal" />
+                        <Widget key="measurement-help" widget={helpWidget} mode="normal" />
+                    </>
+                ) : null}
+                {isDev() ? <NotificationPopover /> : null}
+            </div>
+
+        </>
+    );
+});
+
+export { Widgets };
diff --git a/frontend/app/workspace/workspace.tsx b/frontend/app/workspace/workspace.tsx
index 6a03e3b95f..c4abd13ea0 100644
--- a/frontend/app/workspace/workspace.tsx
+++ b/frontend/app/workspace/workspace.tsx
@@ -4,150 +4,13 @@
 import { ErrorBoundary } from "@/app/element/errorboundary";
 import { CenteredDiv } from "@/app/element/quickelems";
 import { ModalsRenderer } from "@/app/modals/modalsrenderer";
-import { NotificationPopover } from "@/app/notification/notificationpopover";
-import { ContextMenuModel } from "@/app/store/contextmenu";
-import { RpcApi } from "@/app/store/wshclientapi";
-import { TabRpcClient } from "@/app/store/wshrpcutil";
 import { TabBar } from "@/app/tab/tabbar";
 import { TabContent } from "@/app/tab/tabcontent";
-import { atoms, createBlock, getApi, isDev } from "@/store/global";
-import { fireAndForget, isBlank, makeIconClass } from "@/util/util";
-import clsx from "clsx";
+import { Widgets } from "@/app/workspace/widgets";
+import { atoms } from "@/store/global";
 import { useAtomValue } from "jotai";
 import { memo } from "react";
 
-const iconRegex = /^[a-z0-9-]+$/;
-
-function keyLen(obj: Object): number {
-    if (obj == null) {
-        return 0;
-    }
-    return Object.keys(obj).length;
-}
-
-function sortByDisplayOrder(wmap: { [key: string]: WidgetConfigType }): WidgetConfigType[] {
-    if (wmap == null) {
-        return [];
-    }
-    const wlist = Object.values(wmap);
-    wlist.sort((a, b) => {
-        return (a["display:order"] ?? 0) - (b["display:order"] ?? 0);
-    });
-    return wlist;
-}
-
-const Widgets = memo(() => {
-    const fullConfig = useAtomValue(atoms.fullConfigAtom);
-    const helpWidget: WidgetConfigType = {
-        icon: "circle-question",
-        label: "help",
-        blockdef: {
-            meta: {
-                view: "help",
-            },
-        },
-    };
-    const tipsWidget: WidgetConfigType = {
-        icon: "lightbulb",
-        label: "tips",
-        blockdef: {
-            meta: {
-                view: "tips",
-            },
-        },
-    };
-    const showHelp = fullConfig?.settings?.["widget:showhelp"] ?? true;
-    const widgets = sortByDisplayOrder(fullConfig?.widgets);
-
-    const handleWidgetsBarContextMenu = (e: React.MouseEvent) => {
-        e.preventDefault();
-        const menu: ContextMenuItem[] = [
-            {
-                label: "Edit widgets.json",
-                click: () => {
-                    fireAndForget(async () => {
-                        const path = `${getApi().getConfigDir()}/widgets.json`;
-                        const blockDef: BlockDef = {
-                            meta: { view: "preview", file: path },
-                        };
-                        await createBlock(blockDef, false, true);
-                    });
-                },
-            },
-            {
-                label: "Show Help Widgets",
-                submenu: [
-                    {
-                        label: "On",
-                        type: "checkbox",
-                        checked: showHelp,
-                        click: () => {
-                            fireAndForget(async () => {
-                                await RpcApi.SetConfigCommand(TabRpcClient, { "widget:showhelp": true });
-                            });
-                        },
-                    },
-                    {
-                        label: "Off",
-                        type: "checkbox",
-                        checked: !showHelp,
-                        click: () => {
-                            fireAndForget(async () => {
-                                await RpcApi.SetConfigCommand(TabRpcClient, { "widget:showhelp": false });
-                            });
-                        },
-                    },
-                ],
-            },
-        ];
-        ContextMenuModel.showContextMenu(menu, e);
-    };
-
-    return (
-        <div
-            className="flex flex-col w-12 overflow-hidden py-1 -ml-1 select-none"
-            onContextMenu={handleWidgetsBarContextMenu}
-        >
-            {widgets?.map((data, idx) => <Widget key={`widget-${idx}`} widget={data} />)}
-            <div className="flex-grow" />
-            {showHelp ? (
-                <>
-                    <Widget key="tips" widget={tipsWidget} />
-                    <Widget key="help" widget={helpWidget} />
-                </>
-            ) : null}
-            {isDev() ? <NotificationPopover /> : null}
-        </div>
-    );
-});
-
-async function handleWidgetSelect(widget: WidgetConfigType) {
-    const blockDef = widget.blockdef;
-    createBlock(blockDef, widget.magnified);
-}
-
-const Widget = memo(({ widget }: { widget: WidgetConfigType }) => {
-    return (
-        <div
-            className={clsx(
-                "flex flex-col justify-center items-center w-full py-1.5 pr-0.5 text-secondary text-lg overflow-hidden rounded-sm hover:bg-hoverbg hover:text-white cursor-pointer",
-                widget["display:hidden"] && "hidden"
-            )}
-            onClick={() => handleWidgetSelect(widget)}
-            title={widget.description || widget.label}
-        >
-            <div style={{ color: widget.color }}>
-                <i className={makeIconClass(widget.icon, true, { defaultIcon: "browser" })}></i>
-            </div>
-            {!isBlank(widget.label) ? (
-                <div className="text-xxs mt-0.5 w-full px-0.5 text-center whitespace-nowrap overflow-hidden">
-                    {widget.label}
-                </div>
-            ) : null}
-        </div>
-    );
-});
-
 const WorkspaceElem = memo(() => {
     const tabId = useAtomValue(atoms.staticTabId);
     const ws = useAtomValue(atoms.workspace);