diff --git a/apps/web/src/components/views/rooms/EditMessageComposer.tsx b/apps/web/src/components/views/rooms/EditMessageComposer.tsx
index 970d8cffcd..598765881d 100644
--- a/apps/web/src/components/views/rooms/EditMessageComposer.tsx
+++ b/apps/web/src/components/views/rooms/EditMessageComposer.tsx
@@ -439,7 +439,7 @@ class EditMessageComposer extends React.Component<IEditMessageComposerProps, ISt
                 this.editorRef.current?.insertQuotedMessage(payload.event);
             } else if (payload.text) {
                 this.editorRef.current?.insertPlaintext(payload.text);
-            }
+            } // File inserts explcitly unsupported in the edit composer.
         } else if (payload.action === Action.FocusEditMessageComposer) {
             this.editorRef.current.focus();
         }
diff --git a/apps/web/src/components/views/rooms/MessageComposerButtons.tsx b/apps/web/src/components/views/rooms/MessageComposerButtons.tsx
index 8dd7e19571..c1d78533c1 100644
--- a/apps/web/src/components/views/rooms/MessageComposerButtons.tsx
+++ b/apps/web/src/components/views/rooms/MessageComposerButtons.tsx
@@ -1,4 +1,5 @@
 /*
+Copyright 2026 Element Creations Ltd.
 Copyright 2024 New Vector Ltd.
 Copyright 2022 The Matrix.org Foundation C.I.C.
 
@@ -14,38 +15,32 @@ import {
     THREAD_RELATION_TYPE,
     M_POLL_START,
 } from "matrix-js-sdk/src/matrix";
-import React, { type JSX, createContext, type ReactElement, type ReactNode, useContext, useRef } from "react";
+import React, { type JSX, createContext, type ReactElement, type ReactNode, useContext } from "react";
 import {
-    AttachmentIcon,
     MicOnIcon,
     OverflowHorizontalIcon,
     PollsIcon,
     StickerIcon,
     TextFormattingIcon,
 } from "@vector-im/compound-design-tokens/assets/web/icons";
-import { ComposerApiFileUploadLocal } from "@element-hq/element-web-module-api";
-import { MultiOptionButton } from "@element-hq/web-shared-components";
+import { UploadButton, useViewModel } from "@element-hq/web-shared-components";
 
 import { _t } from "../../../languageHandler";
 import { CollapsibleButton } from "./CollapsibleButton";
 import { type MenuProps } from "../../structures/ContextMenu";
-import dis from "../../../dispatcher/dispatcher";
 import ErrorDialog from "../dialogs/ErrorDialog";
 import { LocationButton } from "../location";
 import Modal from "../../../Modal";
 import PollCreateDialog from "../elements/PollCreateDialog";
 import { MatrixClientPeg } from "../../../MatrixClientPeg";
-import ContentMessages from "../../../ContentMessages";
 import MatrixClientContext from "../../../contexts/MatrixClientContext";
-import { useDispatcher } from "../../../hooks/useDispatcher";
-import { chromeFileInputFix } from "../../../utils/BrowserWorkarounds";
 import IconizedContextMenu, { IconizedContextMenuOptionList } from "../context_menus/IconizedContextMenu";
 import { EmojiButton } from "./EmojiButton";
 import { filterBoolean } from "../../../utils/arrays";
 import { useSettingValue } from "../../../hooks/useSettings";
 import AccessibleButton, { type ButtonEvent } from "../elements/AccessibleButton";
 import { useScopedRoomContext } from "../../../contexts/ScopedRoomContext.tsx";
-import { ModuleApi } from "../../../modules/Api.ts";
+import { useRoomUploadViewModel } from "../../../viewmodels/room/RoomUploadViewModel.tsx";
 
 interface IProps {
     addEmoji: (emoji: string) => boolean;
@@ -69,6 +64,8 @@ export const OverflowMenuContext = createContext<OverflowMenuCloser | null>(null
 
 const MessageComposerButtons: React.FC<IProps> = (props: IProps) => {
     const matrixClient = useContext(MatrixClientContext);
+    const roomUploadVM = useRoomUploadViewModel();
+    const { extraUploadOptions } = useViewModel(roomUploadVM);
     const { room, narrow } = useScopedRoomContext("room", "narrow");
 
     const isWysiwygLabEnabled = useSettingValue("feature_wysiwyg_composer");
@@ -92,7 +89,7 @@ const MessageComposerButtons: React.FC<IProps> = (props: IProps) => {
             ),
         ];
         moreButtons = [
-            <UploadButton key="uploads" />, // props passed via UploadButtonContext
+            <UploadButton key="upload" options={extraUploadOptions} onSelect={roomUploadVM.onUploadOptionSelected} />,
             showStickersButton(props),
             voiceRecordingButton(props, narrow),
             props.showPollsButton ? pollButton(room, props.relation) : null,
@@ -109,7 +106,7 @@ const MessageComposerButtons: React.FC<IProps> = (props: IProps) => {
             ) : (
                 emojiButton(props)
             ),
-            <UploadButton key="uploads" />, // props passed via UploadButtonContext
+            <UploadButton key="upload" options={extraUploadOptions} onSelect={roomUploadVM.onUploadOptionSelected} />,
         ];
         moreButtons = [
             showStickersButton(props),
@@ -129,7 +126,7 @@ const MessageComposerButtons: React.FC<IProps> = (props: IProps) => {
     });
 
     return (
-        <UploadButtonContextProvider roomId={room.roomId} relation={props.relation}>
+        <>
             {mainButtons}
             {moreButtons.length > 0 && (
                 <AccessibleButton
@@ -152,7 +149,7 @@ const MessageComposerButtons: React.FC<IProps> = (props: IProps) => {
                     </OverflowMenuContext.Provider>
                 </IconizedContextMenu>
             )}
-        </UploadButtonContextProvider>
+        </>
     );
 };
 
@@ -167,110 +164,6 @@ function emojiButton(props: IProps): ReactElement {
     );
 }
 
-const UploadButton: React.FC = () => {
-    const overflowMenuCloser = useContext(OverflowMenuContext);
-    const onLocalUploadClick = useContext(UploadButtonContext);
-    const { room } = useScopedRoomContext("room");
-
-    const onLocalClick = (): void => {
-        onLocalUploadClick?.();
-        overflowMenuCloser?.(); // close overflow menu
-    };
-
-    const options = [...ModuleApi.instance.composer.fileUploadOptions.values()].map((uploadOption) => {
-        if (uploadOption.type === ComposerApiFileUploadLocal) {
-            return {
-                icon: AttachmentIcon,
-                label: _t("common|attachment"),
-                onSelect: onLocalClick,
-            };
-        } else {
-            return {
-                icon: uploadOption.icon,
-                label: uploadOption.label,
-                onSelect: () => {
-                    uploadOption.onSelected(room!.roomId, (res) => {
-                        console.log("Do something with the result", res);
-                    });
-                },
-            };
-        }
-    });
-
-    return (
-        <MultiOptionButton
-            options={options}
-            multipleOptionsButton={{ label: _t("action|upload_file"), icon: AttachmentIcon }}
-        />
-    );
-};
-
-type UploadButtonFn = () => void;
-export const UploadButtonContext = createContext<UploadButtonFn | null>(null);
-
-interface IUploadButtonProps {
-    roomId: string;
-    relation?: IEventRelation;
-    children: ReactNode;
-}
-
-// We put the file input outside the UploadButton component so that it doesn't get killed when the context menu closes.
-const UploadButtonContextProvider: React.FC<IUploadButtonProps> = ({ roomId, relation, children }) => {
-    const cli = useContext(MatrixClientContext);
-    const roomContext = useScopedRoomContext("timelineRenderingType", "replyToEvent");
-    const uploadInput = useRef<HTMLInputElement>(null);
-
-    const onUploadClick = (): void => {
-        if (cli?.isGuest()) {
-            dis.dispatch({ action: "require_registration" });
-            return;
-        }
-        uploadInput.current?.click();
-    };
-
-    useDispatcher(dis, (payload) => {
-        if (roomContext.timelineRenderingType === payload.context && payload.action === "upload_file") {
-            onUploadClick();
-        }
-    });
-
-    const onUploadFileInputChange = (ev: React.ChangeEvent<HTMLInputElement>): void => {
-        if (ev.target.files?.length === 0) return;
-
-        // Take a copy, so we can safely reset the value of the form control
-        ContentMessages.sharedInstance().sendContentListToRoom(
-            Array.from(ev.target.files!),
-            roomId,
-            relation,
-            roomContext.replyToEvent,
-            cli,
-            roomContext.timelineRenderingType,
-        );
-
-        // This is the onChange handler for a file form control, but we're
-        // not keeping any state, so reset the value of the form control
-        // to empty.
-        // NB. we need to set 'value': the 'files' property is immutable.
-        ev.target.value = "";
-    };
-
-    const uploadInputStyle = { display: "none" };
-    return (
-        <UploadButtonContext.Provider value={onUploadClick}>
-            {children}
-
-            <input
-                ref={uploadInput}
-                type="file"
-                style={uploadInputStyle}
-                multiple
-                onClick={chromeFileInputFix}
-                onChange={onUploadFileInputChange}
-            />
-        </UploadButtonContext.Provider>
-    );
-};
-
 function showStickersButton(props: IProps): ReactElement | null {
     return props.showStickersButton ? (
         <CollapsibleButton
diff --git a/apps/web/src/components/views/rooms/SendMessageComposer.tsx b/apps/web/src/components/views/rooms/SendMessageComposer.tsx
index 29492108f5..035a9aefa9 100644
--- a/apps/web/src/components/views/rooms/SendMessageComposer.tsx
+++ b/apps/web/src/components/views/rooms/SendMessageComposer.tsx
@@ -48,7 +48,7 @@ import { type ActionPayload } from "../../../dispatcher/payloads";
 import { decorateStartSendingTime, sendRoundTripMetric } from "../../../sendTimePerformanceMetrics";
 import RoomContext, { TimelineRenderingType } from "../../../contexts/RoomContext";
 import DocumentPosition from "../../../editor/position";
-import { ComposerType } from "../../../dispatcher/payloads/ComposerInsertPayload";
+import { ComposerInsertPayload, ComposerType } from "../../../dispatcher/payloads/ComposerInsertPayload";
 import { getSlashCommand, isSlashCommand, runSlashCommand, shouldSendAnyway } from "../../../editor/commands";
 import { KeyBindingAction } from "../../../accessibility/KeyboardShortcuts";
 import { PosthogAnalytics } from "../../../PosthogAnalytics";
@@ -541,18 +541,22 @@ export class SendMessageComposer extends React.Component<ISendMessageComposerPro
                     this.editorRef.current?.focus();
                 }
                 break;
-            case Action.ComposerInsert:
-                if (payload.timelineRenderingType !== this.context.timelineRenderingType) break;
-                if (payload.composerType !== ComposerType.Send) break;
+            case Action.ComposerInsert: {
+                const insertPayload = payload as ComposerInsertPayload;
+                if (insertPayload.timelineRenderingType !== this.context.timelineRenderingType) break;
+                if (insertPayload.composerType !== ComposerType.Send) break;
 
-                if (payload.userId) {
-                    this.editorRef.current?.insertMention(payload.userId);
-                } else if (payload.event) {
-                    this.editorRef.current?.insertQuotedMessage(payload.event);
-                } else if (payload.text) {
-                    this.editorRef.current?.insertPlaintext(payload.text);
+                if (insertPayload.userId) {
+                    this.editorRef.current?.insertMention(insertPayload.userId);
+                } else if (insertPayload.event) {
+                    this.editorRef.current?.insertQuotedMessage(insertPayload.event);
+                } else if (insertPayload.text) {
+                    this.editorRef.current?.insertPlaintext(insertPayload.text);
+                } else if (insertPayload.files) {
+                    this.props.uploadVm.initiateViaInputFiles(insertPayload.files);
                 }
                 break;
+            }
         }
     };
 
diff --git a/apps/web/src/components/views/rooms/wysiwyg_composer/hooks/useWysiwygSendActionHandler.ts b/apps/web/src/components/views/rooms/wysiwyg_composer/hooks/useWysiwygSendActionHandler.ts
index fcab8f4547..6a988e5717 100644
--- a/apps/web/src/components/views/rooms/wysiwyg_composer/hooks/useWysiwygSendActionHandler.ts
+++ b/apps/web/src/components/views/rooms/wysiwyg_composer/hooks/useWysiwygSendActionHandler.ts
@@ -15,10 +15,11 @@ import { TimelineRenderingType } from "../../../../../contexts/RoomContext";
 import { useDispatcher } from "../../../../../hooks/useDispatcher";
 import { focusComposer } from "./utils";
 import { type ComposerFunctions } from "../types";
-import { ComposerType } from "../../../../../dispatcher/payloads/ComposerInsertPayload";
+import { ComposerInsertPayload, ComposerType } from "../../../../../dispatcher/payloads/ComposerInsertPayload";
 import { useComposerContext } from "../ComposerContext";
 import { setSelection } from "../utils/selection";
 import { useScopedRoomContext } from "../../../../../contexts/ScopedRoomContext.tsx";
+import { useRoomUploadViewModel } from "../../../../../viewmodels/room/RoomUploadViewModel.tsx";
 
 export function useWysiwygSendActionHandler(
     disabled: boolean,
@@ -27,6 +28,7 @@ export function useWysiwygSendActionHandler(
 ): void {
     const roomContext = useScopedRoomContext("timelineRenderingType");
     const composerContext = useComposerContext();
+    const uploadVm = useRoomUploadViewModel();
     const timeoutId = useRef<number | null>(null);
 
     const handler = useCallback(
@@ -50,21 +52,25 @@ export function useWysiwygSendActionHandler(
                     composerFunctions.clear();
                     focusComposer(composerElement, context, roomContext, timeoutId);
                     break;
-                case Action.ComposerInsert:
-                    if (payload.timelineRenderingType !== roomContext.timelineRenderingType) break;
-                    if (payload.composerType !== ComposerType.Send) break;
+                case Action.ComposerInsert: {
+                    const insertPayload = payload as ComposerInsertPayload;
+                    if (insertPayload.timelineRenderingType !== roomContext.timelineRenderingType) break;
+                    if (insertPayload.composerType !== ComposerType.Send) break;
 
-                    if (payload.userId) {
+                    if (insertPayload.userId) {
                         // TODO insert mention - see SendMessageComposer
-                    } else if (payload.event) {
+                    } else if (insertPayload.event) {
                         // TODO insert quote message - see SendMessageComposer
-                    } else if (payload.text) {
+                    } else if (insertPayload.text) {
                         setSelection(composerContext.selection).then(() => composerFunctions.insertText(payload.text));
+                    } else if (insertPayload.files) {
+                        uploadVm.initiateViaInputFiles(insertPayload.files);
                     }
                     break;
+                }
             }
         },
-        [disabled, composerElement, roomContext, composerFunctions, composerContext],
+        [disabled, composerElement, roomContext, composerFunctions, composerContext, uploadVm],
     );
 
     useDispatcher(defaultDispatcher, handler);
diff --git a/apps/web/src/dispatcher/payloads/ComposerInsertPayload.ts b/apps/web/src/dispatcher/payloads/ComposerInsertPayload.ts
index 597db9712e..7981d1e87b 100644
--- a/apps/web/src/dispatcher/payloads/ComposerInsertPayload.ts
+++ b/apps/web/src/dispatcher/payloads/ComposerInsertPayload.ts
@@ -29,4 +29,11 @@ interface IComposerInsertPlaintextPayload extends IBaseComposerInsertPayload {
     text: string;
 }
 
-export type ComposerInsertPayload = IComposerInsertMentionPayload | IComposerInsertPlaintextPayload;
+interface IComposerInsertFilesPayload extends IBaseComposerInsertPayload {
+    files: File[];
+}
+
+export type ComposerInsertPayload =
+    | IComposerInsertMentionPayload
+    | IComposerInsertPlaintextPayload
+    | IComposerInsertFilesPayload;
diff --git a/apps/web/src/modules/ComposerApi.ts b/apps/web/src/modules/ComposerApi.ts
index ebe193ef46..f95ce8f1ab 100644
--- a/apps/web/src/modules/ComposerApi.ts
+++ b/apps/web/src/modules/ComposerApi.ts
@@ -5,27 +5,68 @@ SPDX-License-Identifier: AGPL-3.0-only OR GPL-3.0-only OR LicenseRef-Element-Com
 Please see LICENSE files in the repository root for full details.
 */
 
-import { type ComposerApi as ModuleComposerApi } from "@element-hq/element-web-module-api";
+import {
+    type ComposerApi as ModuleComposerApi,
+    type ComposerApiFileUploadOption,
+} from "@element-hq/element-web-module-api";
+import { TypedEventEmitter } from "matrix-js-sdk/src/matrix";
 
 import type { MatrixDispatcher } from "../dispatcher/dispatcher";
 import { Action } from "../dispatcher/actions";
 import type { ComposerInsertPayload } from "../dispatcher/payloads/ComposerInsertPayload";
 
-export class ComposerApi implements ModuleComposerApi {
+export enum ModuleComposerApiEvents {
+    UploaderOptionsChanged = "uploaderOptionsChanged",
+}
+
+interface ModuleComposerApiEventsMap {
+    [ModuleComposerApiEvents.UploaderOptionsChanged]: (option: ComposerApiFileUploadOption) => void;
+}
+
+export class ComposerApi
+    extends TypedEventEmitter<ModuleComposerApiEvents, ModuleComposerApiEventsMap>
+    implements ModuleComposerApi
+{
     private allowLocalFileUploads = true;
+    private readonly configuredFileUploadOptions = new Map<string, ComposerApiFileUploadOption>();
 
-    public constructor(private readonly dispatcher: MatrixDispatcher) {}
+    public constructor(private readonly dispatcher: MatrixDispatcher) {
+        super();
+    }
 
+    /**
+     * Is the user permitted to upload local files in any way.
+     */
     public get localFileUploadsAllowed(): boolean {
         return this.allowLocalFileUploads;
     }
 
-    public addFileUploadOption(option): void {}
+    /**
+     * List of possible file upload options.
+     */
+    public get fileUploadOptions(): ComposerApiFileUploadOption[] {
+        return [...this.configuredFileUploadOptions.values()];
+    }
 
     public disableLocalFileUploads(): void {
         this.allowLocalFileUploads = false;
     }
 
+    public addFileUploadOption(option: ComposerApiFileUploadOption): void {
+        if (this.configuredFileUploadOptions.has(option.type)) {
+            throw new Error(`Option "${option.type}" already exists `);
+        }
+        this.configuredFileUploadOptions.set(option.type, option);
+        this.emit(ModuleComposerApiEvents.UploaderOptionsChanged, option);
+    }
+
+    public openFileUploadConfirmation(files: File[]): void {
+        this.dispatcher.dispatch({
+            action: Action.ComposerInsert,
+            files,
+        } satisfies ComposerInsertPayload);
+    }
+
     public insertPlaintextIntoComposer(plaintext: string): void {
         this.dispatcher.dispatch({
             action: Action.ComposerInsert,
diff --git a/apps/web/src/viewmodels/room/RoomUploadViewModel.tsx b/apps/web/src/viewmodels/room/RoomUploadViewModel.tsx
index 38b2721815..54d901f0a8 100644
--- a/apps/web/src/viewmodels/room/RoomUploadViewModel.tsx
+++ b/apps/web/src/viewmodels/room/RoomUploadViewModel.tsx
@@ -6,6 +6,7 @@
  */
 
 import { BaseViewModel, useCreateAutoDisposedViewModel } from "@element-hq/web-shared-components";
+import type { ComposerApiFileUploadOption } from "@element-hq/element-web-module-api";
 import { logger as rootLogger } from "matrix-js-sdk/src/logger";
 import React, {
     type ChangeEventHandler,
@@ -32,23 +33,15 @@ import { chromeFileInputFix } from "../../utils/BrowserWorkarounds";
 import type { MatrixDispatcher } from "../../dispatcher/dispatcher";
 import defaultDispatcher from "../../dispatcher/dispatcher";
 import { ModuleApi } from "../../modules/Api";
+import { ModuleComposerApiEvents } from "../../modules/ComposerApi";
 
 const logger = rootLogger.getChild("RoomUploadViewModel");
 
-export interface RoomUploadViewSnapshot {
-    mayUpload: boolean;
-}
-
-export interface RoomUploadViewActions {
-    initiateViaInputFiles(files: FileList | null): Promise<void>;
-    initiateViaDataTransfer(dataTransfer: DataTransfer): Promise<void>;
-    openUploadDialog(): void;
-}
-
 export class RoomUploadViewModel
     extends BaseViewModel<RoomUploadViewSnapshot, Record<string, never>>
     implements RoomUploadViewActions
 {
+    private readonly extraUploadSelectFns = new Map<string, ComposerApiFileUploadOption["onSelected"]>();
     public constructor(
         private readonly room: Room,
         private readonly client: MatrixClient,
@@ -57,16 +50,27 @@ export class RoomUploadViewModel
         private replyToEvent: MatrixEvent | undefined,
         private threadRelation: IEventRelation | undefined,
         public readonly openUploadDialog: () => void,
+        private readonly moduleComposerApi = ModuleApi.instance.composer,
     ) {
         super(
             {},
             {
                 mayUpload: ModuleApi.instance.composer.localFileUploadsAllowed ?? room.maySendMessage(),
+                extraUploadOptions: moduleComposerApi.fileUploadOptions.map((option) => ({
+                    type: option.type,
+                    label: option.label,
+                    icon: option.icon,
+                })),
             },
         );
+        for (const option of moduleComposerApi.fileUploadOptions) {
+            this.extraUploadSelectFns.set(option.type, option.onSelected);
+        }
         room.on(RoomEvent.CurrentStateUpdated, this.onRoomCurrentStateUpdated);
+        moduleComposerApi.on(ModuleComposerApiEvents.UploaderOptionsChanged, this.onUploaderOptionsChanged);
         this.disposables.track(() => {
             room.off(RoomEvent.CurrentStateUpdated, this.onRoomCurrentStateUpdated);
+            moduleComposerApi.off(ModuleComposerApiEvents.UploaderOptionsChanged, this.onUploaderOptionsChanged);
         });
     }
 
@@ -76,6 +80,20 @@ export class RoomUploadViewModel
         });
     };
 
+    private onUploaderOptionsChanged = (option: ComposerApiFileUploadOption): void => {
+        this.extraUploadSelectFns.set(option.type, option.onSelected);
+        this.snapshot.merge({
+            extraUploadOptions: [
+                ...this.snapshot.current.extraUploadOptions,
+                {
+                    type: option.type,
+                    label: option.label,
+                    icon: option.icon,
+                },
+            ],
+        });
+    };
+
     public setReplyToEvent = (replyToEvent?: MatrixEvent): void => {
         this.replyToEvent = replyToEvent;
     };
@@ -128,6 +146,17 @@ export class RoomUploadViewModel
         }
     };
 
+    public onUploadOptionSelected = (type: ComposerApiFileUploadOption["type"]): void => {
+        const fn = this.extraUploadSelectFns.get(type);
+        if (!fn) {
+            throw Error("Unexpectedly called onUploadOptionSelected with an unknown type");
+        }
+        fn(this.room.roomId, {
+            inReplyToEventId: this.replyToEvent?.getId(),
+            relType: this.threadRelation?.rel_type,
+        });
+    };
+
     private checkCanUpload(): boolean {
         if (this.client.isGuest()) {
             this.dispatcher.dispatch({ action: "require_registration" });
diff --git a/packages/module-api/element-web-module-api.api.md b/packages/module-api/element-web-module-api.api.md
index b712958f87..8452872c20 100644
--- a/packages/module-api/element-web-module-api.api.md
+++ b/packages/module-api/element-web-module-api.api.md
@@ -105,7 +105,7 @@ export interface ComposerApi {
     addFileUploadOption(option: ComposerApiFileUploadOption): void;
     disableLocalFileUploads(): void;
     insertPlaintextIntoComposer(plaintext: string): void;
-    openFileUploadConfirmation(file: File | DataTransfer): void;
+    openFileUploadConfirmation(file: File[]): void;
 }
 
 // @alpha
@@ -113,13 +113,10 @@ export type ComposerApiFileUploadOption = {
     type: string;
     label: string;
     icon?: ComponentType<SVGAttributes<SVGElement>>;
-    onSelected: (roomId: string, relation?: ComposerApiFileUploadRelation) => Promise<void> | void;
-};
-
-// @public (undocumented)
-export type ComposerApiFileUploadRelation = {
-    inReplyToEventId?: string;
-    relType?: "m.thread" | "m";
+    onSelected: (roomId: string, relation?: {
+        inReplyToEventId?: string;
+        relType?: string;
+    }) => Promise<void> | void;
 };
 
 // @public
@@ -241,15 +238,6 @@ export interface ExtrasApi {
     setSpacePanelItem(spaceKey: string, props: SpacePanelItemProps): void;
 }
 
-// @alpha
-export type FileUploadResult = {
-    mxc: string;
-} | {
-    file: File;
-} | {
-    blob: Blob;
-} | null;
-
 // @public
 export interface I18nApi {
     humanizeTime(this: void, timeMillis: number): string;
diff --git a/packages/module-api/src/api/composer.ts b/packages/module-api/src/api/composer.ts
index 9a8f11c027..4525ab03b2 100644
--- a/packages/module-api/src/api/composer.ts
+++ b/packages/module-api/src/api/composer.ts
@@ -7,11 +7,6 @@ Please see LICENSE files in the repository root for full details.
 
 import { ComponentType, SVGAttributes } from "react";
 
-export type ComposerApiFileUploadRelation = {
-    inReplyToEventId?: string;
-    relType?: "m.thread" | "m";
-};
-
 /**
  * An option presented to the user for uploading a file.
  * @alpha Unlikely to change
@@ -31,21 +26,20 @@ export type ComposerApiFileUploadOption = {
      */
     icon?: ComponentType<SVGAttributes<SVGElement>>;
     /**
-     * Function called when the option is selected. The room ID
-     * @param roomId
-     * @param relation
-     * @param onFileSelected
+     * Function called when the option is selected.
+     * @param roomId - The room ID of the room in focus.
+     * @param relation - Whether or not a thread and/or reply is in focus.
      * @returns
      */
-    onSelected: (roomId: string, relation?: ComposerApiFileUploadRelation) => Promise<void> | void;
+    onSelected: (
+        roomId: string,
+        relation?: {
+            inReplyToEventId?: string;
+            relType?: string;
+        },
+    ) => Promise<void> | void;
 };
 
-/**
- * Result from a file upload.
- * @alpha Unlikely to change
- */
-export type FileUploadResult = { mxc: string } | { file: File } | { blob: Blob } | null;
-
 /**
  * API to interact with the message composer.
  * @alpha Likely to change
@@ -53,7 +47,6 @@ export type FileUploadResult = { mxc: string } | { file: File } | { blob: Blob }
 export interface ComposerApi {
     /**
      * Add a new file upload option for the user.
-     * Use {@link ComposerApiFileUploadLocal} to alter the local file upload logic.
      * @throws If another option is already using the same `type`.
      * @alpha Likely to change
      */
@@ -66,7 +59,7 @@ export interface ComposerApi {
      * Open the file upload confirmation dialog. This may be used in conjunction
      * with `addFileUploadOption` to support an alternative file upload kind.
      */
-    openFileUploadConfirmation(file: File | DataTransfer): void;
+    openFileUploadConfirmation(file: File[]): void;
     /**
      * Insert plaintext into the current composer.
      * @param plaintext - The plain text to insert
diff --git a/packages/shared-components/__vis__/linux/__baselines__/room/composer/UploadButton/UploadButton.stories.tsx/default-auto.png b/packages/shared-components/__vis__/linux/__baselines__/room/composer/UploadButton/UploadButton.stories.tsx/default-auto.png
new file mode 100644
index 0000000000..0dd6842eba
Binary files /dev/null and b/packages/shared-components/__vis__/linux/__baselines__/room/composer/UploadButton/UploadButton.stories.tsx/default-auto.png differ
diff --git a/packages/shared-components/__vis__/linux/__baselines__/room/composer/UploadButton/UploadButton.stories.tsx/with-one-option-auto.png b/packages/shared-components/__vis__/linux/__baselines__/room/composer/UploadButton/UploadButton.stories.tsx/with-one-option-auto.png
new file mode 100644
index 0000000000..0dd6842eba
Binary files /dev/null and b/packages/shared-components/__vis__/linux/__baselines__/room/composer/UploadButton/UploadButton.stories.tsx/with-one-option-auto.png differ
diff --git a/packages/shared-components/src/i18n/strings/en_EN.json b/packages/shared-components/src/i18n/strings/en_EN.json
index fe6d4e0865..691ab4adb9 100644
--- a/packages/shared-components/src/i18n/strings/en_EN.json
+++ b/packages/shared-components/src/i18n/strings/en_EN.json
@@ -238,6 +238,9 @@
             "view_image": "View image"
         }
     },
+    "composer": {
+        "attachment_button_label": "Open attachment menu"
+    },
     "widget": {
         "context_menu": {
             "move_left": "Move left",
diff --git a/packages/shared-components/src/index.ts b/packages/shared-components/src/index.ts
index a4e45bc386..58bb64e88e 100644
--- a/packages/shared-components/src/index.ts
+++ b/packages/shared-components/src/index.ts
@@ -9,21 +9,25 @@
 export * from "./audio/Clock";
 export * from "./audio/PlayPauseButton";
 export * from "./audio/SeekBar";
-export * from "./core/avatar/AvatarWithDetails";
-export * from "./composer/Banner";
+export * from "./core/AvatarWithDetails";
+export * from "./core/roving";
+export * from "./room/composer/Banner";
+export * from "./room/composer/UploadButton";
 export * from "./crypto/SasEmoji";
+export * from "./room/timeline/ReadMarker";
 export * from "./room/timeline/event-tile/body/EventContentBodyView";
 export * from "./room/timeline/event-tile/body/RedactedBodyView";
 export * from "./room/timeline/event-tile/body/MFileBodyView";
+export * from "./room/timeline/event-tile/body/MImageBodyView";
 export * from "./room/timeline/event-tile/body/MVideoBodyView";
 export * from "./room/timeline/event-tile/body/TextualBodyView";
 export * from "./room/timeline/event-tile/EventTileView/TileErrorView";
 export * from "./core/pill-input/Pill";
 export * from "./core/pill-input/PillInput";
-export * from "./core/MultiOptionButton";
 export * from "./room/RoomStatusBar";
 export * from "./room/WidgetPip";
 export * from "./room/HistoryVisibilityBadge";
+export * from "./room/right-panel/WidgetContextMenuView";
 export * from "./room/timeline/DateSeparatorView";
 export * from "./room/timeline/TimelineSeparator";
 export * from "./room/timeline/event-tile/actions/ActionBarView";
@@ -44,16 +48,15 @@ export * from "./core/rich-list/RichItem";
 export * from "./core/rich-list/RichList";
 export * from "./room-list/RoomListHeaderView";
 export * from "./room-list/RoomListSearchView";
-export * from "./room-list/RoomListSectionHeaderView";
 export * from "./room-list/RoomListView";
-export * from "./room-list/RoomListItemView";
-export * from "./room-list/RoomListItemAccessibilityWrapper";
+export * from "./room-list/VirtualizedRoomListView/RoomListItemAccessibilityWrapper/RoomListItemView";
 export * from "./room-list/RoomListPrimaryFilters";
 export * from "./room-list/VirtualizedRoomListView";
+export * from "./room-list/VirtualizedRoomListView/RoomListSectionHeaderView";
+export * from "./room-list/VirtualizedRoomListView/RoomListItemAccessibilityWrapper";
 export * from "./core/utils/Box";
 export * from "./core/utils/Flex";
 export * from "./core/utils/LinkedText";
-export * from "./right-panel/WidgetContextMenu";
 export * from "./core/VirtualizedList";
 export * from "./resize";
 
diff --git a/packages/shared-components/src/room/composer/UploadButton/UploadButton.stories.tsx b/packages/shared-components/src/room/composer/UploadButton/UploadButton.stories.tsx
new file mode 100644
index 0000000000..4d540e1be7
--- /dev/null
+++ b/packages/shared-components/src/room/composer/UploadButton/UploadButton.stories.tsx
@@ -0,0 +1,73 @@
+/*
+ * Copyright (c) 2026 Element Creations Ltd.
+ *
+ * SPDX-License-Identifier: AGPL-3.0-only OR GPL-3.0-only OR LicenseRef-Element-Commercial
+ * Please see LICENSE files in the repository root for full details.
+ */
+
+import React, { type JSX } from "react";
+import { type Meta, type StoryFn } from "@storybook/react-vite";
+import { fn } from "storybook/test";
+import { AttachmentIcon, ReactionIcon } from "@vector-im/compound-design-tokens/assets/web/icons";
+
+import { UploadButton, type UploadButtonViewActions, type UploadButtonViewSnapshot } from "./UploadButton";
+import { useMockedViewModel } from "../../../core/viewmodel";
+import { withViewDocs } from "../../../../.storybook/withViewDocs";
+
+const UploadButtonWrapperImpl = ({
+    onUploadOptionSelected,
+    ...rest
+}: UploadButtonViewSnapshot & UploadButtonViewActions): JSX.Element => {
+    const vm = useMockedViewModel(rest, {
+        onUploadOptionSelected,
+    });
+    return <UploadButton vm={vm} />;
+};
+
+const UploadButtonWrapper = withViewDocs(UploadButtonWrapperImpl, UploadButton);
+
+export default {
+    title: "Room/UploadButton",
+    component: UploadButtonWrapper,
+    tags: ["autodocs"],
+    args: {
+        onUploadOptionSelected: fn(),
+        options: [
+            {
+                type: "local",
+                label: "Attachment",
+                icon: AttachmentIcon,
+            },
+        ],
+    },
+} satisfies Meta<typeof UploadButtonWrapper>;
+
+const Template: StoryFn<typeof UploadButtonWrapper> = (args) => <UploadButtonWrapper {...args} />;
+
+export const Default = Template.bind({});
+Default.args = {
+    options: [
+        {
+            type: "local",
+            label: "Attachment",
+            icon: AttachmentIcon,
+        },
+        {
+            label: "Fun Button",
+            icon: ReactionIcon,
+            type: "fun",
+        },
+    ],
+};
+
+export const WithOneOption = Template.bind({});
+
+WithOneOption.args = {
+    options: [
+        {
+            type: "local",
+            label: "Attachment",
+            icon: AttachmentIcon,
+        },
+    ],
+};
diff --git a/packages/shared-components/src/room/composer/UploadButton/UploadButton.test.tsx b/packages/shared-components/src/room/composer/UploadButton/UploadButton.test.tsx
new file mode 100644
index 0000000000..d2737a2b33
--- /dev/null
+++ b/packages/shared-components/src/room/composer/UploadButton/UploadButton.test.tsx
@@ -0,0 +1,23 @@
+/*
+ * Copyright (c) 2026 Element Creations Ltd.
+ *
+ * SPDX-License-Identifier: AGPL-3.0-only OR GPL-3.0-only OR LicenseRef-Element-Commercial
+ * Please see LICENSE files in the repository root for full details.
+ */
+import React from "react";
+import { render } from "@test-utils";
+import { describe, it, expect } from "vitest";
+import { composeStories } from "@storybook/react-vite";
+import { userEvent } from "vitest/browser";
+import { fn } from "storybook/test";
+
+import * as stories from "./UploadButton.stories.tsx";
+
+const { Default } = composeStories(stories);
+
+describe("UploadButton", () => {
+    it("renders a default button", () => {
+        const { container } = render(<Default />);
+        expect(container).toMatchSnapshot();
+    });
+});
diff --git a/packages/shared-components/src/room/composer/UploadButton/UploadButton.tsx b/packages/shared-components/src/room/composer/UploadButton/UploadButton.tsx
new file mode 100644
index 0000000000..2d66070a62
--- /dev/null
+++ b/packages/shared-components/src/room/composer/UploadButton/UploadButton.tsx
@@ -0,0 +1,105 @@
+/*
+ * Copyright (c) 2026 Element Creations Ltd.
+ *
+ * SPDX-License-Identifier: AGPL-3.0-only OR GPL-3.0-only OR LicenseRef-Element-Commercial
+ * Please see LICENSE files in the repository root for full details.
+ */
+
+import React, {
+    type ReactElement,
+    type PropsWithChildren,
+    useState,
+    type ComponentProps,
+    type SVGAttributes,
+    type ComponentType,
+    useCallback,
+    type MouseEventHandler,
+} from "react";
+import { IconButton, Menu, MenuItem } from "@vector-im/compound-web";
+import { AttachmentIcon } from "@vector-im/compound-design-tokens/assets/web/icons";
+
+import { useI18n } from "../../../core/i18n/i18nContext";
+import { useViewModel, type ViewModel } from "../../../core/viewmodel";
+
+export interface UploadButtonViewSnapshot {
+    mayUpload: boolean;
+    options: { type: string; label: string; icon: ComponentType<SVGAttributes<SVGElement>> }[];
+}
+
+export interface UploadButtonViewActions {
+    onUploadOptionSelected(type: string): void;
+}
+
+/**
+ * A button that may have one or more options that the user can select.
+ *
+ * @example
+ * ```tsx
+ *   <UploadButton vm={} />
+ * ```
+ */
+export function UploadButton({
+    vm,
+    ...rootButtonProps
+}: PropsWithChildren<
+    { vm: ViewModel<UploadButtonViewSnapshot, UploadButtonViewActions> } & ComponentProps<typeof IconButton>
+>): ReactElement {
+    const i18n = useI18n();
+    const [open, setOpen] = useState(false);
+    const { options } = useViewModel(vm);
+    // Shift click is a shortcut to selecting the first item.
+    const onMenuClick: MouseEventHandler<HTMLButtonElement> = useCallback(
+        (ev) => {
+            if (!ev.shiftKey) {
+                return;
+            }
+            ev.preventDefault();
+            ev.stopPropagation();
+            vm.onUploadOptionSelected(options[0].type);
+        },
+        [options, vm],
+    );
+    if (options.length === 1) {
+        const { label, icon: Icon } = options[0];
+        return (
+            <IconButton
+                tooltip={label}
+                {...rootButtonProps}
+                title={label}
+                onClick={() => vm.onUploadOptionSelected(options[0].type)}
+            >
+                <Icon />
+            </IconButton>
+        );
+    }
+
+    const trigger = (
+        <IconButton
+            tooltip={i18n.translate("common|attachment")}
+            onClick={onMenuClick}
+            {...rootButtonProps}
+            title={i18n.translate("common|attachment")}
+        >
+            <AttachmentIcon />
+        </IconButton>
+    );
+
+    return (
+        <Menu
+            side="top"
+            title={i18n.translate("composer|attachment_button_label")}
+            trigger={trigger}
+            open={open}
+            onOpenChange={(o) => setOpen(o)}
+        >
+            {options.map((o) => (
+                <MenuItem
+                    key={o.label}
+                    label={o.label}
+                    Icon={o.icon}
+                    onSelect={() => vm.onUploadOptionSelected(o.type)}
+                />
+            ))}
+        </Menu>
+    );
+}
diff --git a/packages/shared-components/src/room/composer/UploadButton/index.ts b/packages/shared-components/src/room/composer/UploadButton/index.ts
new file mode 100644
index 0000000000..2bbcd04eaa
--- /dev/null
+++ b/packages/shared-components/src/room/composer/UploadButton/index.ts
@@ -0,0 +1,8 @@
+/*
+ * Copyright (c) 2026 Element Creations Ltd.
+ *
+ * SPDX-License-Identifier: AGPL-3.0-only OR GPL-3.0-only OR LicenseRef-Element-Commercial
+ * Please see LICENSE files in the repository root for full details.
+ */
+
+export * from "./UploadButton";