diff --git a/assets/js/phoenix_live_view/constants.js b/assets/js/phoenix_live_view/constants.js
index 8daa747e45..77a78417b0 100644
--- a/assets/js/phoenix_live_view/constants.js
+++ b/assets/js/phoenix_live_view/constants.js
@@ -13,6 +13,7 @@ export const PHX_EVENT_CLASSES = [
   "phx-focus-loading",
   "phx-hook-loading",
 ];
+export const PHX_DROP_TARGET_ACTIVE_CLASS = "phx-drop-target-active";
 export const PHX_COMPONENT = "data-phx-component";
 export const PHX_VIEW_REF = "data-phx-view";
 export const PHX_LIVE_LINK = "data-phx-link";
diff --git a/assets/js/phoenix_live_view/live_socket.js b/assets/js/phoenix_live_view/live_socket.js
index 042d01f8dd..e5aa889e66 100644
--- a/assets/js/phoenix_live_view/live_socket.js
+++ b/assets/js/phoenix_live_view/live_socket.js
@@ -28,6 +28,7 @@ import {
   PHX_REF_SRC,
   PHX_RELOAD_STATUS,
   PHX_RUNTIME_HOOK,
+  PHX_DROP_TARGET_ACTIVE_CLASS,
 } from "./constants";
 
 import {
@@ -37,6 +38,7 @@ import {
   debug,
   maybe,
   logError,
+  eventContainsFiles,
 } from "./utils";
 
 import Browser from "./browser";
@@ -666,14 +668,55 @@ export default class LiveSocket {
       },
     );
     this.on("dragover", (e) => e.preventDefault());
+    this.on("dragenter", (e) => {
+      const dropzone = closestPhxBinding(
+        e.target,
+        this.binding(PHX_DROP_TARGET),
+      );
+
+      if (!dropzone || !(dropzone instanceof HTMLElement)) {
+        return;
+      }
+
+      if (eventContainsFiles(e)) {
+        this.js().addClass(dropzone, PHX_DROP_TARGET_ACTIVE_CLASS);
+      }
+    });
+    this.on("dragleave", (e) => {
+      const dropzone = closestPhxBinding(
+        e.target,
+        this.binding(PHX_DROP_TARGET),
+      );
+
+      if (!dropzone || !(dropzone instanceof HTMLElement)) {
+        return;
+      }
+
+      // Avoid add/remove jitter in the case that we drag into a new child and that child would
+      // resolve their closest drop target to the current dropzone element
+      const rect = dropzone.getBoundingClientRect();
+      if (
+        e.clientX <= rect.left ||
+        e.clientX >= rect.right ||
+        e.clientY <= rect.top ||
+        e.clientY >= rect.bottom
+      ) {
+        this.js().removeClass(dropzone, PHX_DROP_TARGET_ACTIVE_CLASS);
+      }
+    });
     this.on("drop", (e) => {
       e.preventDefault();
-      const dropTargetId = maybe(
-        closestPhxBinding(e.target, this.binding(PHX_DROP_TARGET)),
-        (trueTarget) => {
-          return trueTarget.getAttribute(this.binding(PHX_DROP_TARGET));
-        },
+
+      const dropzone = closestPhxBinding(
+        e.target,
+        this.binding(PHX_DROP_TARGET),
       );
+      if (!dropzone || !(dropzone instanceof HTMLElement)) {
+        return;
+      }
+      this.js().removeClass(dropzone, PHX_DROP_TARGET_ACTIVE_CLASS);
+
+      const dropTargetId = dropzone.getAttribute(this.binding(PHX_DROP_TARGET));
       const dropTarget = dropTargetId && document.getElementById(dropTargetId);
       const files = Array.from(e.dataTransfer.files || []);
       if (
diff --git a/assets/js/phoenix_live_view/utils.js b/assets/js/phoenix_live_view/utils.js
index b358a73781..71cd33a45f 100644
--- a/assets/js/phoenix_live_view/utils.js
+++ b/assets/js/phoenix_live_view/utils.js
@@ -94,3 +94,14 @@ export const channelUploader = function (entries, onError, resp, liveSocket) {
     entryUploader.upload();
   });
 };
+
+export const eventContainsFiles = (e) => {
+  if (e.dataTransfer.types) {
+    for (let i = 0; i < e.dataTransfer.types.length; i++) {
+      if (e.dataTransfer.types[i] === "Files") {
+        return true;
+      }
+    }
+  }
+  return false;
+};
diff --git a/guides/server/uploads.md b/guides/server/uploads.md
index 9d630ae1fa..bc01a0fec1 100644
--- a/guides/server/uploads.md
+++ b/guides/server/uploads.md
@@ -115,6 +115,36 @@ Upload entries are created when a file is added to the form
 input and each will exist until it has been consumed,
 following a successfully completed upload.
 
+### Styling the drop target
+
+Phoenix LiveView listens for drag events in the browser,
+and will annotate the drop target element with the `phx-drop-target-active` class
+when a user is dragging an element over the drop target.
+
+When using TailwindCSS, one may create a custom variant that can be used in conjunction
+with this class to allow styling things specifically when the user is dragging something over the drop target.
+
+```css
+<%!-- assets/app.css --%>
+
+@custom-variant phx-drop-target-active (.phx-drop-target-active&, .phx-drop-target-active &);
+```
+
+This variant can be used in HeEx templates like so:
+
+```heex
+<%!-- lib/my_app_web/live/upload_live.html.heex --%>
+
+<section phx-drop-target={@uploads.avatar.ref} class="phx-drop-target-active:scale-105">
+<!-- ... -->
+</section>
+```
+
+In this example, when a file is dragged over the dropzone element, the element grows in size.
+
+This variant can also be used alongside [Tailwind's arbitrary state selectors](https://tailwindcss.com/docs/hover-focus-and-other-states),
+which can allow one to not only style the element itself, but the entire page, sibling elements, parent elements, and more.
+
 ### Entry validation
 
 Validation occurs automatically based on any conditions
diff --git a/lib/phoenix_component.ex b/lib/phoenix_component.ex
index 58eafe44a3..7af8d5a278 100644
--- a/lib/phoenix_component.ex
+++ b/lib/phoenix_component.ex
@@ -3291,6 +3291,7 @@ defmodule Phoenix.Component do
   </label>
   ```
 
+  The drop target receives the `phx-drop-target-active` class when it is active. For more information, see the [uploads guide](guides/server/uploads.md).
   ## Examples
 
   Rendering a file input: