diff --git a/packages/vscode-extension/src/common/utils.ts b/packages/vscode-extension/src/common/utils.ts
index 43ed9fcbe..63203b498 100644
--- a/packages/vscode-extension/src/common/utils.ts
+++ b/packages/vscode-extension/src/common/utils.ts
@@ -1,5 +1,14 @@
+import { TelemetryEventProperties } from "@vscode/extension-telemetry";
 import { RecordingData } from "./Project";
 
+export interface UtilsEventListener<T> {
+  (event: T): void;
+}
+
+export interface UtilsEventMap {
+  telemetryEnabledChanged: boolean;
+}
+
 export interface UtilsInterface {
   getCommandsCurrentKeyBinding(commandName: string): Promise<string | undefined>;
 
@@ -16,4 +25,18 @@ export interface UtilsInterface {
   openExternalUrl(uriString: string): Promise<void>;
 
   log(type: "info" | "error" | "warn" | "log", message: string, ...args: any[]): Promise<void>;
+
+  sendTelemetry(eventName: string, properties?: TelemetryEventProperties): Promise<void>;
+
+  isTelemetryEnabled(): Promise<boolean>;
+
+  addListener<K extends keyof UtilsEventMap>(
+    eventType: K,
+    listener: UtilsEventListener<UtilsEventMap[K]>
+  ): Promise<void>;
+
+  removeListener<K extends keyof UtilsEventMap>(
+    eventType: K,
+    listener: UtilsEventListener<UtilsEventMap[K]>
+  ): Promise<void>;
 }
diff --git a/packages/vscode-extension/src/utilities/utils.ts b/packages/vscode-extension/src/utilities/utils.ts
index 774ae37a9..0e6ebc718 100644
--- a/packages/vscode-extension/src/utilities/utils.ts
+++ b/packages/vscode-extension/src/utilities/utils.ts
@@ -1,15 +1,18 @@
 import { homedir } from "node:os";
+import { EventEmitter } from "stream";
 import fs from "fs";
 import path from "path";
 import { commands, env, Uri, window } from "vscode";
 import JSON5 from "json5";
 import vscode from "vscode";
+import { TelemetryEventProperties } from "@vscode/extension-telemetry";
 import { Logger } from "../Logger";
 import { extensionContext } from "./extensionContext";
 import { openFileAtPosition } from "./openFileAtPosition";
-import { UtilsInterface } from "../common/utils";
+import { UtilsEventListener, UtilsEventMap, UtilsInterface } from "../common/utils";
 import { Platform } from "./platform";
 import { RecordingData } from "../common/Project";
+import { getTelemetryReporter } from "./telemetry";
 
 type KeybindingType = {
   command: string;
@@ -19,6 +22,14 @@ type KeybindingType = {
 };
 
 export class Utils implements UtilsInterface {
+  private eventEmitter = new EventEmitter();
+
+  constructor() {
+    vscode.env.onDidChangeTelemetryEnabled((telemetryEnabled) => {
+      this.eventEmitter.emit("telemetryEnabledChanged", telemetryEnabled);
+    });
+  }
+
   public async getCommandsCurrentKeyBinding(commandName: string) {
     const packageJsonPath = path.join(extensionContext.extensionPath, "package.json");
     const extensionPackageJson = require(packageJsonPath);
@@ -142,4 +153,25 @@ export class Utils implements UtilsInterface {
     // Combine into the desired format
     return `${year}-${month}-${day} ${hours}.${minutes}.${seconds}`;
   }
+
+  public async sendTelemetry(eventName: string, properties?: TelemetryEventProperties) {
+    getTelemetryReporter().sendTelemetryEvent(eventName, properties);
+  }
+
+  public async isTelemetryEnabled() {
+    return vscode.env.isTelemetryEnabled;
+  }
+
+  async addListener<K extends keyof UtilsEventMap>(
+    eventType: K,
+    listener: UtilsEventListener<UtilsEventMap[K]>
+  ) {
+    this.eventEmitter.addListener(eventType, listener);
+  }
+  async removeListener<K extends keyof UtilsEventMap>(
+    eventType: K,
+    listener: UtilsEventListener<UtilsEventMap[K]>
+  ) {
+    this.eventEmitter.removeListener(eventType, listener);
+  }
 }
diff --git a/packages/vscode-extension/src/webview/components/Feedback.css b/packages/vscode-extension/src/webview/components/Feedback.css
new file mode 100644
index 000000000..e6e83b6ea
--- /dev/null
+++ b/packages/vscode-extension/src/webview/components/Feedback.css
@@ -0,0 +1,76 @@
+.feedback {
+  display: flex;
+  gap: 4px;
+}
+
+.feedback-button {
+  width: 26px;
+  height: 20px;
+  display: flex;
+  align-items: center;
+  justify-content: center;
+  border-radius: 3px;
+  transition: all 250ms 0ms ease-in-out;
+}
+
+.feedback-button:active {
+  transform: scale(0.94);
+}
+
+.feedback-button-large:active {
+  transform: scale(0.96);
+}
+
+.feedback-button:hover span,
+.feedback-button-positive-active span,
+.feedback-button-negative-active span {
+  color: var(--swm-popover-background) !important;
+}
+
+.feedback-button:hover {
+  cursor: pointer;
+}
+
+.feedback-button-large {
+  width: 64px;
+  height: 46px;
+}
+
+.feedback-button-large span {
+  font-size: 24px !important;
+}
+
+.feedback-button-positive {
+  color: var(--green-light-80);
+  border: 1px solid var(--green-light-80);
+}
+
+.feedback-button-positive span {
+  color: var(--green-light-80);
+}
+
+.feedback-button-positive:hover,
+.feedback-button-positive-active {
+  background-color: var(--green-light-80);
+}
+
+.feedback-button-negative {
+  border: 1px solid var(--red-light-80);
+}
+
+.feedback-button-negative span {
+  color: var(--red-light-80);
+}
+
+.feedback-button-negative:hover,
+.feedback-button-negative-active {
+  background-color: var(--red-light-80);
+}
+
+.feedback-prompt {
+  cursor: pointer;
+  font-size: 12px;
+}
+.feedback-prompt:hover {
+  text-decoration: underline;
+}
diff --git a/packages/vscode-extension/src/webview/components/Feedback.tsx b/packages/vscode-extension/src/webview/components/Feedback.tsx
new file mode 100644
index 000000000..a0c37bca2
--- /dev/null
+++ b/packages/vscode-extension/src/webview/components/Feedback.tsx
@@ -0,0 +1,77 @@
+import { Dispatch, MouseEvent, SetStateAction } from "react";
+import "./Feedback.css";
+import classNames from "classnames";
+import { useUtils } from "../providers/UtilsProvider";
+import { Sentiment } from "./SendFeedbackItem";
+
+type FeedbackProps = {
+  sentiment: Sentiment | undefined;
+  setSentiment: Dispatch<SetStateAction<Sentiment | undefined>>;
+};
+
+export function Feedback({ sentiment, setSentiment }: FeedbackProps) {
+  const { sendTelemetry } = useUtils();
+
+  const handleFeedback = (event: MouseEvent<HTMLButtonElement>, pickedSentiment: Sentiment) => {
+    event.preventDefault();
+    sendTelemetry(`feedback:${pickedSentiment}`);
+    setSentiment(pickedSentiment);
+  };
+
+  return (
+    <div className="feedback">
+      {Boolean(sentiment) ? (
+        <p className="feedback-prompt">
+          {sentiment === "positive" ? "What went well?" : "Tell us more"}
+        </p>
+      ) : (
+        <>
+          <FeedbackButton sentiment="positive" onClick={(e) => handleFeedback(e, "positive")} />
+          <FeedbackButton sentiment="negative" onClick={(e) => handleFeedback(e, "negative")} />
+        </>
+      )}
+    </div>
+  );
+}
+
+type FeedbackButtonProps = {
+  sentiment: Sentiment;
+  onClick?: (event: MouseEvent<HTMLButtonElement>) => void;
+  type?: "small" | "large";
+  isActive?: boolean;
+};
+
+export function FeedbackButton({
+  sentiment,
+  onClick,
+  type = "small",
+  isActive,
+}: FeedbackButtonProps) {
+  if (sentiment === "positive") {
+    return (
+      <button
+        className={classNames(
+          "feedback-button feedback-button-positive",
+          isActive && "feedback-button-positive-active",
+          type === "large" && "feedback-button-large"
+        )}
+        type="button"
+        onClick={onClick}>
+        <span className="codicon codicon-thumbsup" />
+      </button>
+    );
+  }
+
+  return (
+    <button
+      className={classNames(
+        "feedback-button feedback-button-negative",
+        isActive && "feedback-button-negative-active",
+        type === "large" && "feedback-button-large"
+      )}
+      type="button"
+      onClick={onClick}>
+      <span className="codicon codicon-thumbsdown" />
+    </button>
+  );
+}
diff --git a/packages/vscode-extension/src/webview/components/SendFeedbackItem.tsx b/packages/vscode-extension/src/webview/components/SendFeedbackItem.tsx
new file mode 100644
index 000000000..6f380918e
--- /dev/null
+++ b/packages/vscode-extension/src/webview/components/SendFeedbackItem.tsx
@@ -0,0 +1,31 @@
+import { useState } from "react";
+import * as DropdownMenu from "@radix-ui/react-dropdown-menu";
+
+import { useModal } from "../providers/ModalProvider";
+import FeedbackView from "../views/FeedbackView";
+import { Feedback } from "./Feedback";
+
+export type Sentiment = "positive" | "negative";
+
+export function SendFeedbackItem() {
+  const { openModal } = useModal();
+
+  const [sentiment, setSentiment] = useState<Sentiment | undefined>();
+
+  return (
+    <DropdownMenu.Item
+      className="dropdown-menu-item"
+      onSelect={() => {
+        openModal(
+          "Do you enjoy using Radon IDE today?",
+          <FeedbackView initialSentiment={sentiment} />
+        );
+      }}>
+      <span className="codicon codicon-feedback" />
+      <div className="dropdown-menu-item-content">
+        Send feedback
+        <Feedback sentiment={sentiment} setSentiment={setSentiment} />
+      </div>
+    </DropdownMenu.Item>
+  );
+}
diff --git a/packages/vscode-extension/src/webview/components/SettingsDropdown.tsx b/packages/vscode-extension/src/webview/components/SettingsDropdown.tsx
index 7e0d59b7d..32d146b31 100644
--- a/packages/vscode-extension/src/webview/components/SettingsDropdown.tsx
+++ b/packages/vscode-extension/src/webview/components/SettingsDropdown.tsx
@@ -11,6 +11,8 @@ import { KeybindingInfo } from "./shared/KeybindingInfo";
 import { useUtils } from "../providers/UtilsProvider";
 import "./shared/SwitchGroup.css";
 import LaunchConfigurationView from "../views/LaunchConfigurationView";
+import { SendFeedbackItem } from "./SendFeedbackItem";
+import { useTelemetry } from "../providers/TelemetryProvider";
 
 interface SettingsDropdownProps {
   children: React.ReactNode;
@@ -23,6 +25,7 @@ function SettingsDropdown({ project, isDeviceRunning, children, disabled }: Sett
   const { panelLocation, update } = useWorkspaceConfig();
   const { openModal } = useModal();
   const { movePanelToNewWindow, reportIssue } = useUtils();
+  const { telemetryEnabled } = useTelemetry();
 
   return (
     <DropdownMenu.Root>
@@ -142,6 +145,7 @@ function SettingsDropdown({ project, isDeviceRunning, children, disabled }: Sett
               <div className="dropdown-menu-item-content">Report Issue</div>
             </span>
           </DropdownMenu.Item>
+          {telemetryEnabled && <SendFeedbackItem />}
         </DropdownMenu.Content>
       </DropdownMenu.Portal>
     </DropdownMenu.Root>
diff --git a/packages/vscode-extension/src/webview/index.jsx b/packages/vscode-extension/src/webview/index.jsx
index 1e793bec6..3089383f4 100644
--- a/packages/vscode-extension/src/webview/index.jsx
+++ b/packages/vscode-extension/src/webview/index.jsx
@@ -11,6 +11,7 @@ import WorkspaceConfigProvider from "./providers/WorkspaceConfigProvider";
 
 import "./styles/theme.css";
 import { UtilsProvider, installLogOverrides } from "./providers/UtilsProvider";
+import { TelemetryProvider } from "./providers/TelemetryProvider";
 import LaunchConfigProvider from "./providers/LaunchConfigProvider";
 
 installLogOverrides();
@@ -22,19 +23,21 @@ root.render(
   <React.StrictMode>
     <ProjectProvider>
       <UtilsProvider>
-        <WorkspaceConfigProvider>
-          <LaunchConfigProvider>
-            <DevicesProvider>
-              <DependenciesProvider>
-                <ModalProvider>
-                  <AlertProvider>
-                    <App />
-                  </AlertProvider>
-                </ModalProvider>
-              </DependenciesProvider>
-            </DevicesProvider>
-          </LaunchConfigProvider>
-        </WorkspaceConfigProvider>
+        <TelemetryProvider>
+          <WorkspaceConfigProvider>
+            <LaunchConfigProvider>
+              <DevicesProvider>
+                <DependenciesProvider>
+                  <ModalProvider>
+                    <AlertProvider>
+                      <App />
+                    </AlertProvider>
+                  </ModalProvider>
+                </DependenciesProvider>
+              </DevicesProvider>
+            </LaunchConfigProvider>
+          </WorkspaceConfigProvider>
+        </TelemetryProvider>
       </UtilsProvider>
     </ProjectProvider>
   </React.StrictMode>
diff --git a/packages/vscode-extension/src/webview/providers/TelemetryProvider.tsx b/packages/vscode-extension/src/webview/providers/TelemetryProvider.tsx
new file mode 100644
index 000000000..2f69bb5a5
--- /dev/null
+++ b/packages/vscode-extension/src/webview/providers/TelemetryProvider.tsx
@@ -0,0 +1,33 @@
+import { createContext, PropsWithChildren, useContext, useEffect, useMemo, useState } from "react";
+import { useUtils } from "./UtilsProvider";
+
+type TelemetryContextProps = { telemetryEnabled: boolean };
+
+const TelemetryContext = createContext<TelemetryContextProps>({ telemetryEnabled: false });
+
+export function TelemetryProvider({ children }: PropsWithChildren) {
+  const utils = useUtils();
+  const [telemetryEnabled, setTelemetryEnabled] = useState(false);
+
+  useEffect(() => {
+    utils.isTelemetryEnabled().then(setTelemetryEnabled);
+    utils.addListener("telemetryEnabledChanged", setTelemetryEnabled);
+
+    return () => {
+      utils.removeListener("telemetryEnabledChanged", setTelemetryEnabled);
+    };
+  }, []);
+
+  const contextValue = useMemo(() => ({ telemetryEnabled }), [telemetryEnabled]);
+
+  return <TelemetryContext.Provider value={contextValue}>{children}</TelemetryContext.Provider>;
+}
+
+export function useTelemetry() {
+  const context = useContext(TelemetryContext);
+
+  if (context === undefined) {
+    throw new Error("useTelemetry must be used within a TelemetryContextProvider");
+  }
+  return context;
+}
diff --git a/packages/vscode-extension/src/webview/views/FeedbackView.css b/packages/vscode-extension/src/webview/views/FeedbackView.css
new file mode 100644
index 000000000..2270cfa05
--- /dev/null
+++ b/packages/vscode-extension/src/webview/views/FeedbackView.css
@@ -0,0 +1,71 @@
+.feedback-textarea {
+  flex: 1;
+  background-color: var(--swm-input-background);
+  color: var(--swm-default-text);
+  height: auto;
+  padding: 8px;
+  margin: 0 4px;
+  border: 1px;
+  border-radius: 4px;
+  line-height: 1.5;
+  box-shadow: var(--swm-input-shadow);
+  font-family: var(--font-family);
+  resize: none;
+}
+
+.feedback-textarea::placeholder {
+  color: var(--swm-secondary-text);
+}
+
+.feedback-buttons-container {
+  display: flex;
+  align-items: center;
+  justify-content: center;
+  gap: 16px;
+  margin: 16px 0;
+}
+
+.feedback-button-wrapper {
+  display: flex;
+  flex-direction: column;
+  align-items: center;
+  justify-content: center;
+}
+
+.feedback-button-label {
+  color: var(--swm-default-text);
+  font-size: 12px;
+  margin-top: 8px;
+}
+
+.feedback-label-optional {
+  color: var(--swm-secondary-text);
+  font-weight: normal;
+  margin-left: 0;
+}
+
+.feedback-report-issue {
+  line-height: 1.5;
+  color: var(--swm-secondary-text);
+}
+
+.feedback-report-issue a {
+  color: var(--swm-default-text);
+}
+
+.feedback-report-issue a:hover {
+  text-decoration: underline;
+}
+
+.feedback-row {
+  display: flex;
+  justify-content: flex-end;
+  gap: 8px;
+}
+
+.feedback-thank-you {
+  color: var(--swm-default-text);
+  font-weight: 500;
+  font-size: 18px;
+  text-align: center;
+}
diff --git a/packages/vscode-extension/src/webview/views/FeedbackView.tsx b/packages/vscode-extension/src/webview/views/FeedbackView.tsx
new file mode 100644
index 000000000..5513c3eb5
--- /dev/null
+++ b/packages/vscode-extension/src/webview/views/FeedbackView.tsx
@@ -0,0 +1,94 @@
+import { useEffect, useState } from "react";
+import { FieldValues, SubmitHandler, useForm } from "react-hook-form";
+import Button from "../components/shared/Button";
+import { FeedbackButton } from "../components/Feedback";
+import "./FeedbackView.css";
+import { useModal } from "../providers/ModalProvider";
+import { useUtils } from "../providers/UtilsProvider";
+import { Sentiment } from "../components/SendFeedbackItem";
+
+const CLOSE_MODAL_AFTER = 2400;
+
+type FeedbackViewProps = {
+  initialSentiment: Sentiment | undefined;
+};
+
+function FeedbackView({ initialSentiment }: FeedbackViewProps) {
+  const [isFeedbackSent, setFeedbackSent] = useState(false);
+  const { closeModal, showHeader } = useModal();
+  const { register, handleSubmit } = useForm();
+  const { sendTelemetry } = useUtils();
+  const [sentiment, setSentiment] = useState(initialSentiment);
+
+  const onSubmit: SubmitHandler<FieldValues> = (e) => {
+    const { message } = e;
+    sendTelemetry(`feedback:${sentiment}`, { message });
+    showHeader(false);
+    setFeedbackSent(true);
+  };
+
+  useEffect(() => {
+    if (isFeedbackSent) {
+      const timer = setTimeout(() => {
+        closeModal();
+        showHeader(true);
+      }, CLOSE_MODAL_AFTER);
+      return () => clearTimeout(timer);
+    }
+  }, [isFeedbackSent]);
+
+  if (isFeedbackSent) {
+    return <p className="feedback-thank-you">Thank you for your feedback!</p>;
+  }
+
+  return (
+    <form className="container" onSubmit={handleSubmit(onSubmit)}>
+      <div className="feedback-buttons-container">
+        <div className="feedback-button-wrapper">
+          <FeedbackButton
+            sentiment="positive"
+            type="large"
+            onClick={() => setSentiment("positive")}
+            isActive={sentiment === "positive"}
+          />
+          <span className="feedback-button-label">I do!</span>
+        </div>
+        <div className="feedback-button-wrapper">
+          <FeedbackButton
+            sentiment="negative"
+            type="large"
+            onClick={() => setSentiment("negative")}
+            isActive={sentiment === "negative"}
+          />
+          <span className="feedback-button-label">Not really...</span>
+        </div>
+      </div>
+      <textarea
+        {...register("message")}
+        className="feedback-textarea"
+        placeholder="Tell us why (optional)"
+        rows={5}
+      />
+      <p className="feedback-report-issue">
+        We don't include any details about the project, your setup or the logs. Have a problem?{" "}
+        <a
+          href="https://github.com/software-mansion/radon-ide/issues/new/choose"
+          target="_blank"
+          rel="noopener noreferrer">
+          Report an issue on GitHub
+        </a>
+        .
+      </p>
+      <div className="feedback-row">
+        <Button type="secondary" onClick={closeModal}>
+          Cancel
+        </Button>
+        <Button type="ternary" disabled={!sentiment}>
+          Send feedback
+        </Button>
+      </div>
+    </form>
+  );
+}
+
+export default FeedbackView;