diff --git a/app/javascript/flavours/glitch/features/compose/components/sensitive_button.jsx b/app/javascript/flavours/glitch/features/compose/components/sensitive_button.jsx
index deb401bfb744e4..de7d033ed076e4 100644
--- a/app/javascript/flavours/glitch/features/compose/components/sensitive_button.jsx
+++ b/app/javascript/flavours/glitch/features/compose/components/sensitive_button.jsx
@@ -21,11 +21,11 @@ const messages = defineMessages({
 export const SensitiveButton = () => {
   const intl = useIntl();
 
-  const spoilersAlwaysOn = useAppSelector((state) => state.getIn(['local_settings', 'always_show_spoilers_field']));
-  const spoilerText = useAppSelector((state) => state.getIn(['compose', 'spoiler_text']));
-  const sensitive = useAppSelector((state) => state.getIn(['compose', 'sensitive']));
-  const spoiler = useAppSelector((state) => state.getIn(['compose', 'spoiler']));
-  const mediaCount = useAppSelector((state) => state.getIn(['compose', 'media_attachments']).size);
+  const spoilersAlwaysOn = useAppSelector((state) => state.local_settings.getIn(['always_show_spoilers_field']));
+  const spoilerText = useAppSelector((state) => state.compose.get('spoiler_text'));
+  const sensitive = useAppSelector((state) => state.compose.get('sensitive'));
+  const spoiler = useAppSelector((state) => state.compose.get('spoiler'));
+  const mediaCount = useAppSelector((state) => state.compose.get('media_attachments').size);
   const disabled = spoilersAlwaysOn ? (spoilerText && spoilerText.length > 0) : spoiler;
 
   const active = sensitive || (spoilersAlwaysOn && spoilerText && spoilerText.length > 0);
diff --git a/app/javascript/flavours/glitch/features/compose/components/upload.jsx b/app/javascript/flavours/glitch/features/compose/components/upload.jsx
deleted file mode 100644
index 790d76264d2bdd..00000000000000
--- a/app/javascript/flavours/glitch/features/compose/components/upload.jsx
+++ /dev/null
@@ -1,81 +0,0 @@
-import PropTypes from 'prop-types';
-import { useCallback } from 'react';
-
-import { FormattedMessage } from 'react-intl';
-
-import classNames from 'classnames';
-
-import { useDispatch, useSelector } from 'react-redux';
-
-import spring from 'react-motion/lib/spring';
-
-import CloseIcon from '@/material-icons/400-20px/close.svg?react';
-import EditIcon from '@/material-icons/400-24px/edit.svg?react';
-import WarningIcon from '@/material-icons/400-24px/warning.svg?react';
-import { undoUploadCompose, initMediaEditModal } from 'flavours/glitch/actions/compose';
-import { Blurhash } from 'flavours/glitch/components/blurhash';
-import { Icon }  from 'flavours/glitch/components/icon';
-import Motion from 'flavours/glitch/features/ui/util/optional_motion';
-
-export const Upload = ({ id, onDragStart, onDragEnter, onDragEnd }) => {
-  const dispatch = useDispatch();
-  const media = useSelector(state => state.getIn(['compose', 'media_attachments']).find(item => item.get('id') === id));
-  const sensitive = useSelector(state => state.getIn(['compose', 'sensitive']));
-
-  const handleUndoClick = useCallback(() => {
-    dispatch(undoUploadCompose(id));
-  }, [dispatch, id]);
-
-  const handleFocalPointClick = useCallback(() => {
-    dispatch(initMediaEditModal(id));
-  }, [dispatch, id]);
-
-  const handleDragStart = useCallback(() => {
-    onDragStart(id);
-  }, [onDragStart, id]);
-
-  const handleDragEnter = useCallback(() => {
-    onDragEnter(id);
-  }, [onDragEnter, id]);
-
-  if (!media) {
-    return null;
-  }
-
-  const focusX = media.getIn(['meta', 'focus', 'x']);
-  const focusY = media.getIn(['meta', 'focus', 'y']);
-  const x = ((focusX /  2) + .5) * 100;
-  const y = ((focusY / -2) + .5) * 100;
-  const missingDescription = (media.get('description') || '').length === 0;
-
-  return (
-    <div className='compose-form__upload' draggable onDragStart={handleDragStart} onDragEnter={handleDragEnter} onDragEnd={onDragEnd}>
-      <Motion defaultStyle={{ scale: 0.8 }} style={{ scale: spring(1, { stiffness: 180, damping: 12 }) }}>
-        {({ scale }) => (
-          <div className='compose-form__upload__thumbnail' style={{ transform: `scale(${scale})`, backgroundImage: !sensitive ? `url(${media.get('preview_url')})` : null, backgroundPosition: `${x}% ${y}%` }}>
-            {sensitive && <Blurhash
-              hash={media.get('blurhash')}
-              className='compose-form__upload__preview'
-            />}
-
-            <div className='compose-form__upload__actions'>
-              <button type='button' className='icon-button compose-form__upload__delete' onClick={handleUndoClick}><Icon icon={CloseIcon} /></button>
-              <button type='button' className='icon-button' onClick={handleFocalPointClick}><Icon icon={EditIcon} /> <FormattedMessage id='upload_form.edit' defaultMessage='Edit' /></button>
-            </div>
-
-            <div className='compose-form__upload__warning'>
-              <button type='button' className={classNames('icon-button', { active: missingDescription })} onClick={handleFocalPointClick}>{missingDescription && <Icon icon={WarningIcon} />} ALT</button>
-            </div>
-          </div>
-        )}
-      </Motion>
-    </div>
-  );
-};
-
-Upload.propTypes = {
-  id: PropTypes.string,
-  onDragEnter: PropTypes.func,
-  onDragStart: PropTypes.func,
-  onDragEnd: PropTypes.func,
-};
diff --git a/app/javascript/flavours/glitch/features/compose/components/upload.tsx b/app/javascript/flavours/glitch/features/compose/components/upload.tsx
new file mode 100644
index 00000000000000..a583a8d81d5b33
--- /dev/null
+++ b/app/javascript/flavours/glitch/features/compose/components/upload.tsx
@@ -0,0 +1,130 @@
+import { useCallback } from 'react';
+
+import { FormattedMessage } from 'react-intl';
+
+import classNames from 'classnames';
+
+import { useSortable } from '@dnd-kit/sortable';
+import { CSS } from '@dnd-kit/utilities';
+
+import CloseIcon from '@/material-icons/400-20px/close.svg?react';
+import EditIcon from '@/material-icons/400-24px/edit.svg?react';
+import WarningIcon from '@/material-icons/400-24px/warning.svg?react';
+import {
+  undoUploadCompose,
+  initMediaEditModal,
+} from 'flavours/glitch/actions/compose';
+import { Blurhash } from 'flavours/glitch/components/blurhash';
+import { Icon } from 'flavours/glitch/components/icon';
+import type { MediaAttachment } from 'flavours/glitch/models/media_attachment';
+import { useAppDispatch, useAppSelector } from 'flavours/glitch/store';
+
+export const Upload: React.FC<{
+  id: string;
+  dragging?: boolean;
+  overlay?: boolean;
+  tall?: boolean;
+  wide?: boolean;
+}> = ({ id, dragging, overlay, tall, wide }) => {
+  const dispatch = useAppDispatch();
+  const media = useAppSelector(
+    (state) =>
+      state.compose // eslint-disable-line @typescript-eslint/no-unsafe-call
+        .get('media_attachments') // eslint-disable-line @typescript-eslint/no-unsafe-member-access
+        .find((item: MediaAttachment) => item.get('id') === id) as  // eslint-disable-line @typescript-eslint/no-unsafe-member-access
+        | MediaAttachment
+        | undefined,
+  );
+  const sensitive = useAppSelector(
+    (state) => state.compose.get('sensitive') as boolean, // eslint-disable-line @typescript-eslint/no-unsafe-call, @typescript-eslint/no-unsafe-member-access
+  );
+
+  const handleUndoClick = useCallback(() => {
+    dispatch(undoUploadCompose(id));
+  }, [dispatch, id]);
+
+  const handleFocalPointClick = useCallback(() => {
+    dispatch(initMediaEditModal(id));
+  }, [dispatch, id]);
+
+  const { attributes, listeners, setNodeRef, transform, transition } =
+    useSortable({ id });
+
+  if (!media) {
+    return null;
+  }
+
+  const focusX = media.getIn(['meta', 'focus', 'x']) as number;
+  const focusY = media.getIn(['meta', 'focus', 'y']) as number;
+  const x = (focusX / 2 + 0.5) * 100;
+  const y = (focusY / -2 + 0.5) * 100;
+  const missingDescription =
+    ((media.get('description') as string | undefined) ?? '').length === 0;
+
+  const style = {
+    transform: CSS.Transform.toString(transform),
+    transition,
+  };
+
+  return (
+    <div
+      className={classNames('compose-form__upload media-gallery__item', {
+        dragging,
+        overlay,
+        'media-gallery__item--tall': tall,
+        'media-gallery__item--wide': wide,
+      })}
+      ref={setNodeRef}
+      style={style}
+      {...attributes}
+      {...listeners}
+    >
+      <div
+        className='compose-form__upload__thumbnail'
+        style={{
+          backgroundImage: !sensitive
+            ? `url(${media.get('preview_url') as string})`
+            : undefined,
+          backgroundPosition: `${x}% ${y}%`,
+        }}
+      >
+        {sensitive && (
+          <Blurhash
+            hash={media.get('blurhash') as string}
+            className='compose-form__upload__preview'
+          />
+        )}
+
+        <div className='compose-form__upload__actions'>
+          <button
+            type='button'
+            className='icon-button compose-form__upload__delete'
+            onClick={handleUndoClick}
+          >
+            <Icon id='close' icon={CloseIcon} />
+          </button>
+          <button
+            type='button'
+            className='icon-button'
+            onClick={handleFocalPointClick}
+          >
+            <Icon id='edit' icon={EditIcon} />{' '}
+            <FormattedMessage id='upload_form.edit' defaultMessage='Edit' />
+          </button>
+        </div>
+
+        <div className='compose-form__upload__warning'>
+          <button
+            type='button'
+            className={classNames('icon-button', {
+              active: missingDescription,
+            })}
+            onClick={handleFocalPointClick}
+          >
+            {missingDescription && <Icon id='warning' icon={WarningIcon} />} ALT
+          </button>
+        </div>
+      </div>
+    </div>
+  );
+};
diff --git a/app/javascript/flavours/glitch/features/compose/components/upload_form.jsx b/app/javascript/flavours/glitch/features/compose/components/upload_form.jsx
deleted file mode 100644
index 2b26735f5e1cc5..00000000000000
--- a/app/javascript/flavours/glitch/features/compose/components/upload_form.jsx
+++ /dev/null
@@ -1,56 +0,0 @@
-import { useRef, useCallback } from 'react';
-
-import { useSelector, useDispatch } from 'react-redux';
-
-import { changeMediaOrder } from 'flavours/glitch/actions/compose';
-
-import { SensitiveButton } from './sensitive_button';
-import { Upload } from './upload';
-import { UploadProgress } from './upload_progress';
-
-export const UploadForm = () => {
-  const dispatch = useDispatch();
-  const mediaIds = useSelector(state => state.getIn(['compose', 'media_attachments']).map(item => item.get('id')));
-  const active = useSelector(state => state.getIn(['compose', 'is_uploading']));
-  const progress = useSelector(state => state.getIn(['compose', 'progress']));
-  const isProcessing = useSelector(state => state.getIn(['compose', 'is_processing']));
-
-  const dragItem = useRef();
-  const dragOverItem = useRef();
-
-  const handleDragStart = useCallback(id => {
-    dragItem.current = id;
-  }, [dragItem]);
-
-  const handleDragEnter = useCallback(id => {
-    dragOverItem.current = id;
-  }, [dragOverItem]);
-
-  const handleDragEnd = useCallback(() => {
-    dispatch(changeMediaOrder(dragItem.current, dragOverItem.current));
-    dragItem.current = null;
-    dragOverItem.current = null;
-  }, [dispatch, dragItem, dragOverItem]);
-
-  return (
-    <>
-      <UploadProgress active={active} progress={progress} isProcessing={isProcessing} />
-
-      {mediaIds.size > 0 && (
-        <div className='compose-form__uploads'>
-          {mediaIds.map(id => (
-            <Upload
-              key={id}
-              id={id}
-              onDragStart={handleDragStart}
-              onDragEnter={handleDragEnter}
-              onDragEnd={handleDragEnd}
-            />
-          ))}
-        </div>
-      )}
-
-      {!mediaIds.isEmpty() && <SensitiveButton />}
-    </>
-  );
-};
diff --git a/app/javascript/flavours/glitch/features/compose/components/upload_form.tsx b/app/javascript/flavours/glitch/features/compose/components/upload_form.tsx
new file mode 100644
index 00000000000000..44bfaa8f384fc0
--- /dev/null
+++ b/app/javascript/flavours/glitch/features/compose/components/upload_form.tsx
@@ -0,0 +1,188 @@
+import { useState, useCallback, useMemo } from 'react';
+
+import { useIntl, defineMessages } from 'react-intl';
+
+import type { List } from 'immutable';
+
+import type {
+  DragStartEvent,
+  DragEndEvent,
+  UniqueIdentifier,
+  Announcements,
+  ScreenReaderInstructions,
+} from '@dnd-kit/core';
+import {
+  DndContext,
+  closestCenter,
+  KeyboardSensor,
+  PointerSensor,
+  useSensor,
+  useSensors,
+  DragOverlay,
+} from '@dnd-kit/core';
+import {
+  SortableContext,
+  sortableKeyboardCoordinates,
+  rectSortingStrategy,
+} from '@dnd-kit/sortable';
+
+import { changeMediaOrder } from 'flavours/glitch/actions/compose';
+import type { MediaAttachment } from 'flavours/glitch/models/media_attachment';
+import { useAppSelector, useAppDispatch } from 'flavours/glitch/store';
+
+import { SensitiveButton } from './sensitive_button';
+import { Upload } from './upload';
+import { UploadProgress } from './upload_progress';
+
+const messages = defineMessages({
+  screenReaderInstructions: {
+    id: 'upload_form.drag_and_drop.instructions',
+    defaultMessage:
+      'To pick up a media attachment, press space or enter. While dragging, use the arrow keys to move the media attachment in any given direction. Press space or enter again to drop the media attachment in its new position, or press escape to cancel.',
+  },
+  onDragStart: {
+    id: 'upload_form.drag_and_drop.on_drag_start',
+    defaultMessage: 'Picked up media attachment {item}.',
+  },
+  onDragOver: {
+    id: 'upload_form.drag_and_drop.on_drag_over',
+    defaultMessage: 'Media attachment {item} was moved.',
+  },
+  onDragEnd: {
+    id: 'upload_form.drag_and_drop.on_drag_end',
+    defaultMessage: 'Media attachment {item} was dropped.',
+  },
+  onDragCancel: {
+    id: 'upload_form.drag_and_drop.on_drag_cancel',
+    defaultMessage:
+      'Dragging was cancelled. Media attachment {item} was dropped.',
+  },
+});
+
+export const UploadForm: React.FC = () => {
+  const dispatch = useAppDispatch();
+  const intl = useIntl();
+  const mediaIds = useAppSelector(
+    (state) =>
+      state.compose // eslint-disable-line @typescript-eslint/no-unsafe-call
+        .get('media_attachments') // eslint-disable-line @typescript-eslint/no-unsafe-member-access
+        .map((item: MediaAttachment) => item.get('id')) as List<string>, // eslint-disable-line @typescript-eslint/no-unsafe-member-access
+  );
+  const active = useAppSelector(
+    (state) => state.compose.get('is_uploading') as boolean, // eslint-disable-line @typescript-eslint/no-unsafe-call, @typescript-eslint/no-unsafe-member-access
+  );
+  const progress = useAppSelector(
+    (state) => state.compose.get('progress') as number, // eslint-disable-line @typescript-eslint/no-unsafe-call, @typescript-eslint/no-unsafe-member-access
+  );
+  const isProcessing = useAppSelector(
+    (state) => state.compose.get('is_processing') as boolean, // eslint-disable-line @typescript-eslint/no-unsafe-call, @typescript-eslint/no-unsafe-member-access
+  );
+  const [activeId, setActiveId] = useState<UniqueIdentifier | null>(null);
+  const sensors = useSensors(
+    useSensor(PointerSensor, {
+      activationConstraint: {
+        distance: 5,
+      },
+    }),
+    useSensor(KeyboardSensor, {
+      coordinateGetter: sortableKeyboardCoordinates,
+    }),
+  );
+
+  const handleDragStart = useCallback(
+    (e: DragStartEvent) => {
+      const { active } = e;
+
+      setActiveId(active.id);
+    },
+    [setActiveId],
+  );
+
+  const handleDragEnd = useCallback(
+    (e: DragEndEvent) => {
+      const { active, over } = e;
+
+      if (over && active.id !== over.id) {
+        dispatch(changeMediaOrder(active.id, over.id));
+      }
+
+      setActiveId(null);
+    },
+    [dispatch, setActiveId],
+  );
+
+  const accessibility: {
+    screenReaderInstructions: ScreenReaderInstructions;
+    announcements: Announcements;
+  } = useMemo(
+    () => ({
+      screenReaderInstructions: {
+        draggable: intl.formatMessage(messages.screenReaderInstructions),
+      },
+
+      announcements: {
+        onDragStart({ active }) {
+          return intl.formatMessage(messages.onDragStart, { item: active.id });
+        },
+
+        onDragOver({ active }) {
+          return intl.formatMessage(messages.onDragOver, { item: active.id });
+        },
+
+        onDragEnd({ active }) {
+          return intl.formatMessage(messages.onDragEnd, { item: active.id });
+        },
+
+        onDragCancel({ active }) {
+          return intl.formatMessage(messages.onDragCancel, { item: active.id });
+        },
+      },
+    }),
+    [intl],
+  );
+
+  return (
+    <>
+      <UploadProgress
+        active={active}
+        progress={progress}
+        isProcessing={isProcessing}
+      />
+
+      {mediaIds.size > 0 && (
+        <div
+          className={`compose-form__uploads media-gallery media-gallery--layout-${mediaIds.size}`}
+        >
+          <DndContext
+            sensors={sensors}
+            collisionDetection={closestCenter}
+            onDragStart={handleDragStart}
+            onDragEnd={handleDragEnd}
+            accessibility={accessibility}
+          >
+            <SortableContext
+              items={mediaIds.toArray()}
+              strategy={rectSortingStrategy}
+            >
+              {mediaIds.map((id, idx) => (
+                <Upload
+                  key={id}
+                  id={id}
+                  dragging={id === activeId}
+                  tall={mediaIds.size < 3 || (mediaIds.size === 3 && idx === 0)}
+                  wide={mediaIds.size === 1}
+                />
+              ))}
+            </SortableContext>
+
+            <DragOverlay>
+              {activeId ? <Upload id={activeId as string} overlay /> : null}
+            </DragOverlay>
+          </DndContext>
+        </div>
+      )}
+
+      {!mediaIds.isEmpty() && <SensitiveButton />}
+    </>
+  );
+};
diff --git a/app/javascript/flavours/glitch/models/media_attachment.ts b/app/javascript/flavours/glitch/models/media_attachment.ts
new file mode 100644
index 00000000000000..0e5b9ab555e354
--- /dev/null
+++ b/app/javascript/flavours/glitch/models/media_attachment.ts
@@ -0,0 +1,2 @@
+// Temporary until we type it correctly
+export type MediaAttachment = Immutable.Map<string, unknown>;
diff --git a/app/javascript/flavours/glitch/styles/components.scss b/app/javascript/flavours/glitch/styles/components.scss
index 211edcc9bea688..72613cbbc4874b 100644
--- a/app/javascript/flavours/glitch/styles/components.scss
+++ b/app/javascript/flavours/glitch/styles/components.scss
@@ -653,19 +653,39 @@ body > [data-popper-placement] {
   }
 
   &__uploads {
-    display: flex;
-    gap: 8px;
     padding: 0 12px;
-    flex-wrap: wrap;
-    align-self: stretch;
-    align-items: flex-start;
-    align-content: flex-start;
-    justify-content: center;
+    aspect-ratio: 3/2;
+  }
+
+  .media-gallery {
+    gap: 8px;
   }
 
   &__upload {
-    flex: 1 1 0;
-    min-width: calc(50% - 8px);
+    position: relative;
+    cursor: grab;
+
+    &.dragging {
+      opacity: 0;
+    }
+
+    &.overlay {
+      height: 100%;
+      border-radius: 8px;
+      pointer-events: none;
+    }
+
+    &__drag-handle {
+      position: absolute;
+      top: 50%;
+      inset-inline-start: 0;
+      transform: translateY(-50%);
+      color: $white;
+      background: transparent;
+      border: 0;
+      padding: 8px 3px;
+      cursor: grab;
+    }
 
     &__actions {
       display: flex;
@@ -686,8 +706,7 @@ body > [data-popper-placement] {
 
     &__thumbnail {
       width: 100%;
-      height: 144px;
-      border-radius: 6px;
+      height: 100%;
       background-position: center;
       background-size: cover;
       background-repeat: no-repeat;
@@ -7602,30 +7621,30 @@ img.modal-warning {
   gap: 2px;
 
   &--layout-2 {
-    .media-gallery__item:nth-child(1) {
+    & > .media-gallery__item:nth-child(1) {
       border-end-end-radius: 0;
       border-start-end-radius: 0;
     }
 
-    .media-gallery__item:nth-child(2) {
+    & > .media-gallery__item:nth-child(2) {
       border-start-start-radius: 0;
       border-end-start-radius: 0;
     }
   }
 
   &--layout-3 {
-    .media-gallery__item:nth-child(1) {
+    & > .media-gallery__item:nth-child(1) {
       border-end-end-radius: 0;
       border-start-end-radius: 0;
     }
 
-    .media-gallery__item:nth-child(2) {
+    & > .media-gallery__item:nth-child(2) {
       border-start-start-radius: 0;
       border-end-start-radius: 0;
       border-end-end-radius: 0;
     }
 
-    .media-gallery__item:nth-child(3) {
+    & > .media-gallery__item:nth-child(3) {
       border-start-start-radius: 0;
       border-end-start-radius: 0;
       border-start-end-radius: 0;
@@ -7633,26 +7652,26 @@ img.modal-warning {
   }
 
   &--layout-4 {
-    .media-gallery__item:nth-child(1) {
+    & > .media-gallery__item:nth-child(1) {
       border-end-end-radius: 0;
       border-start-end-radius: 0;
       border-end-start-radius: 0;
     }
 
-    .media-gallery__item:nth-child(2) {
+    & > .media-gallery__item:nth-child(2) {
       border-start-start-radius: 0;
       border-end-start-radius: 0;
       border-end-end-radius: 0;
     }
 
-    .media-gallery__item:nth-child(3) {
+    & > .media-gallery__item:nth-child(3) {
       border-start-start-radius: 0;
       border-start-end-radius: 0;
       border-end-start-radius: 0;
       border-end-end-radius: 0;
     }
 
-    .media-gallery__item:nth-child(4) {
+    & > .media-gallery__item:nth-child(4) {
       border-start-start-radius: 0;
       border-end-start-radius: 0;
       border-start-end-radius: 0;