diff --git a/web/src/tippyjs.ts b/web/src/tippyjs.ts
index 3815469bdf..78fbf87405 100644
--- a/web/src/tippyjs.ts
+++ b/web/src/tippyjs.ts
@@ -258,6 +258,20 @@ export function initialize(): void {
         appendTo: () => document.body,
     });
 
+    tippy.delegate("body", {
+        target: ".add-task-wrapper",
+        onShow(instance) {
+            const $elem = $(instance.reference);
+            const content = $elem.attr("data-tippy-content");
+            if (content === undefined) {
+                return false;
+            }
+            instance.setContent(content);
+            return undefined;
+        },
+        appendTo: () => document.body,
+    });
+
     $("body").on(
         "blur",
         ".message_control_button, .delete-selected-drafts-button-container",
diff --git a/web/src/todo_widget.ts b/web/src/todo_widget.ts
index 19781bd9a0..83bfab2047 100644
--- a/web/src/todo_widget.ts
+++ b/web/src/todo_widget.ts
@@ -1,4 +1,5 @@
 import $ from "jquery";
+import _ from "lodash";
 import assert from "minimalistic-assert";
 import {z} from "zod";
 
@@ -404,6 +405,13 @@ export function activate({
         const html = render_widgets_todo_widget();
         $elem.html(html);
 
+        // This throttling ensures that the function runs only after the user stops typing.
+        const throttled_update_add_task_button = _.throttle(update_add_task_button, 300);
+        $elem.find("input.add-task").on("keyup", (e) => {
+            e.stopPropagation();
+            throttled_update_add_task_button();
+        });
+
         $elem.find("input.todo-task-list-title").on("keyup", (e) => {
             e.stopPropagation();
             update_edit_controls();
@@ -444,13 +452,10 @@ export function activate({
             const task = $elem.find<HTMLInputElement>("input.add-task").val()?.trim() ?? "";
             const desc = $elem.find<HTMLInputElement>("input.add-desc").val()?.trim() ?? "";
 
-            if (task === "") {
-                return;
-            }
-
             $elem.find("input.add-task").val("").trigger("focus");
             $elem.find("input.add-desc").val("");
 
+            // This case should not generally occur.
             const task_exists = task_data.name_in_use(task);
             if (task_exists) {
                 $elem.find(".widget-error").text($t({defaultMessage: "Task already exists"}));
@@ -462,6 +467,30 @@ export function activate({
         });
     }
 
+    function update_add_task_button(): void {
+        const task = $elem.find<HTMLInputElement>("input.add-task").val()?.trim() ?? "";
+        const task_exists = task_data.name_in_use(task);
+        const $add_task_wrapper = $elem.find(".add-task-wrapper");
+        const $add_task_button = $elem.find("button.add-task");
+
+        if (task === "") {
+            $add_task_wrapper.attr(
+                "data-tippy-content",
+                $t({defaultMessage: "Name the task before adding."}),
+            );
+            $add_task_button.prop("disabled", true);
+        } else if (task_exists) {
+            $add_task_wrapper.attr(
+                "data-tippy-content",
+                $t({defaultMessage: "Cannot add duplicate task."}),
+            );
+            $add_task_button.prop("disabled", true);
+        } else {
+            $add_task_wrapper.removeAttr("data-tippy-content");
+            $add_task_button.prop("disabled", false);
+        }
+    }
+
     function render_results(): void {
         const widget_data = task_data.get_widget_data();
         const html = render_widgets_todo_widget_tasks(widget_data);
@@ -487,6 +516,8 @@ export function activate({
             const data = task_data.handle.strike.outbound(key);
             callback(data);
         });
+
+        update_add_task_button();
     }
 
     const handle_events = function (events: Event[]): void {
diff --git a/web/styles/widgets.css b/web/styles/widgets.css
index f8057358b1..55b4409d7c 100644
--- a/web/styles/widgets.css
+++ b/web/styles/widgets.css
@@ -237,6 +237,13 @@ button {
             transition: 0.2s ease;
             transition-property: background-color, border-color, color;
         }
+
+        &:disabled {
+            cursor: not-allowed;
+            filter: saturate(0);
+            background-color: var(--color-background-zulip-button-disabled);
+            color: hsl(0deg 3% 52%);
+        }
     }
 }
 
@@ -308,3 +315,17 @@ input {
 .current-user-vote {
     background-color: hsl(156deg 10% 90% / 90%);
 }
+
+.add-task-wrapper {
+    display: inline;
+    position: relative;
+    z-index: 1;
+
+    /* Unlike other browsers like Chrome, Microsoft Edge, etc.,
+    Firefox does not automatically display the "not-allowed"
+    cursor for disabled elements. The below css ensures that the
+    correct cursor is shown across all browsers. */
+    &:hover {
+        cursor: not-allowed;
+    }
+}
diff --git a/web/templates/widgets/todo_widget.hbs b/web/templates/widgets/todo_widget.hbs
index 0a593c2217..a7c5f110e4 100644
--- a/web/templates/widgets/todo_widget.hbs
+++ b/web/templates/widgets/todo_widget.hbs
@@ -13,7 +13,9 @@
     <div class="add-task-bar sea-green">
         <input type="text" class="add-task" placeholder="{{t 'New task'}}" />
         <input type="text" class="add-desc" placeholder="{{t 'Description'}}" />
-        <button class="add-task">{{t "Add task" }}</button>
+        <div class="add-task-wrapper">
+            <button class="add-task">{{t "Add task" }}</button>
+        </div>
         <div class="widget-error"></div>
     </div>
 </div>