diff --git a/src/domain/session/room/RoomViewModel.js b/src/domain/session/room/RoomViewModel.js
index a979be09..2586f2b2 100644
--- a/src/domain/session/room/RoomViewModel.js
+++ b/src/domain/session/room/RoomViewModel.js
@@ -182,6 +182,36 @@ export class RoomViewModel extends ViewModel {
         // TODO: dispose file.blob (in the attachment, after upload)
     }
 
+    async _sendPicture() {
+        if (!this.platform.hasReadPixelPermission()) {
+            alert("Please allow canvas image data access, so we can scale your images down.");
+            return;
+        }
+        let file;
+        try {
+            file = await this.platform.openFile("image/*");
+        } catch (err) {
+            return;
+        }
+        const image = await this.platform.loadImage(file.blob);
+        const content = {
+            body: file.name,
+            msgtype: "m.image",
+            info: imageToInfo(image)
+        };
+        const attachments = {
+            "url": this._room.createAttachment(file.blob, file.name),
+        };
+        if (image.maxDimension > 600) {
+            const thumbnail = await image.scale(400);
+            content.info.thumbnail_info = imageToInfo(thumbnail);
+            attachments["info.thumbnail_url"] = 
+                this._room.createAttachment(thumbnail.blob, file.name);
+        }
+        await this._room.sendEvent("m.room.message", content, attachments);
+    }
+    
+
     get composerViewModel() {
         return this._composerVM;
     }
@@ -207,7 +237,11 @@ class ComposerViewModel extends ViewModel {
         return success;
     }
 
-    sendAttachment() {
+    sendPicture() {
+        this._roomVM._sendPicture();
+    }
+
+    sendFile() {
         this._roomVM._sendFile();
     }
 
@@ -226,3 +260,12 @@ class ComposerViewModel extends ViewModel {
         }
     }
 }
+
+function imageToInfo(image) {
+    return {
+        w: image.width,
+        h: image.height,
+        mimetype: image.blob.mimeType,
+        size: image.blob.size
+    };
+}
diff --git a/src/platform/web/dom/ImageHandle.js b/src/platform/web/dom/ImageHandle.js
index 691ead22..dcead27c 100644
--- a/src/platform/web/dom/ImageHandle.js
+++ b/src/platform/web/dom/ImageHandle.js
@@ -30,6 +30,10 @@ export class ImageHandle {
         this._imgElement = imgElement;
     }
 
+    get maxDimension() {
+        return Math.max(this.width, this.height);
+    }
+
     async _getImgElement() {
         if (!this._imgElement) {
             this._imgElement = await loadImgFromBlob(this.blob);
diff --git a/src/platform/web/ui/session/room/MessageComposer.js b/src/platform/web/ui/session/room/MessageComposer.js
index 62b55b15..0609285b 100644
--- a/src/platform/web/ui/session/room/MessageComposer.js
+++ b/src/platform/web/ui/session/room/MessageComposer.js
@@ -15,6 +15,8 @@ limitations under the License.
 */
 
 import {TemplateView} from "../../general/TemplateView.js";
+import {Popup} from "../../general/Popup.js";
+import {Menu} from "../../general/Menu.js";
 
 export class MessageComposer extends TemplateView {
     constructor(viewModel) {
@@ -32,8 +34,8 @@ export class MessageComposer extends TemplateView {
             this._input,
             t.button({
                 className: "sendFile",
-                title: vm.i18n`Send file`,
-                onClick: () => vm.sendAttachment(),
+                title: vm.i18n`Pick attachment`,
+                onClick: evt => this._showAttachmentMenu(evt),
             }, vm.i18n`Send file`),
             t.button({
                 className: "send",
@@ -56,4 +58,25 @@ export class MessageComposer extends TemplateView {
             this._trySend();
         }
     }
+
+    _showAttachmentMenu(evt) {
+        const vm = this.value;
+        const popup = new Popup(new Menu([
+            Menu.option(vm.i18n`Send picture`, () => vm.sendPicture()).setIcon("picture"),
+            Menu.option(vm.i18n`Send file`, () => vm.sendFile()).setIcon("file"),
+        ]));
+        popup.trackInTemplateView(this);
+        popup.showRelativeTo(evt.target, {
+            horizontal: {
+                relativeTo: "end",
+                align: "start",
+                after: 0
+            },
+            vertical: {
+                relativeTo: "end",
+                align: "start",
+                before: 8,
+            }
+        });
+    }
 }