diff --git a/.changeset/chatty-camels-explain.md b/.changeset/chatty-camels-explain.md
new file mode 100644
index 0000000000000..818dbaf10b29f
--- /dev/null
+++ b/.changeset/chatty-camels-explain.md
@@ -0,0 +1,7 @@
+---
+'@rocket.chat/model-typings': patch
+'@rocket.chat/models': patch
+'@rocket.chat/meteor': patch
+---
+
+Fixes `/sendEmailAttachment` to support sending multiple file attachments in a single email
diff --git a/apps/meteor/server/features/EmailInbox/EmailInbox_Outgoing.ts b/apps/meteor/server/features/EmailInbox/EmailInbox_Outgoing.ts
index 8ff7e4a0c5821..8d4a669762280 100644
--- a/apps/meteor/server/features/EmailInbox/EmailInbox_Outgoing.ts
+++ b/apps/meteor/server/features/EmailInbox/EmailInbox_Outgoing.ts
@@ -1,6 +1,7 @@
 import { isIMessageInbox } from '@rocket.chat/core-typings';
-import type { IEmailInbox, IUser, IOmnichannelRoom, SlashCommandCallbackParams } from '@rocket.chat/core-typings';
+import type { IEmailInbox, IUser, IOmnichannelRoom, SlashCommandCallbackParams, IUpload } from '@rocket.chat/core-typings';
 import { Messages, Uploads, LivechatRooms, Rooms, Users } from '@rocket.chat/models';
+import { isTruthy } from '@rocket.chat/tools';
 import { Match } from 'meteor/check';
 import type Mail from 'nodemailer/lib/mailer';
 
@@ -22,6 +23,18 @@ const getRocketCatUser = async (): Promise<IUser | null> => Users.findOneById('r
 const language = settings.get<string>('Language') || 'en';
 const t = i18n.getFixedT(language);
 
+async function buildMailAttachment(file: IUpload): Promise<Mail.Attachment | undefined> {
+	const buffer = await FileUpload.getBuffer(file);
+	if (!buffer) {
+		return;
+	}
+	return {
+		content: buffer,
+		contentType: file.type,
+		filename: file.name,
+	};
+}
+
 // TODO: change these messages with room notifications
 const sendErrorReplyMessage = async (error: string, options: any) => {
 	if (!options?.rid || !options?.msgId) {
@@ -98,12 +111,16 @@ slashCommands.add({
 		}
 
 		const message = await Messages.findOneById(params.trim());
-		if (!message?.file) {
+		if (!message) {
 			return;
 		}
 
-		const room = await Rooms.findOneById<IOmnichannelRoom>(message.rid);
+		const fileRefs = (message.files || [message.file]).filter(isTruthy);
+		if (!fileRefs.length) {
+			return;
+		}
 
+		const room = await Rooms.findOneById<IOmnichannelRoom>(message.rid);
 		if (!room?.email) {
 			return;
 		}
@@ -118,37 +135,35 @@ slashCommands.add({
 			});
 		}
 
-		const file = await Uploads.findOneById(message.file._id);
-
-		if (!file) {
+		const files = await Uploads.find({ _id: { $in: fileRefs.map((f) => f._id) } }).toArray();
+		const emailAttachments = await Promise.all(files.map(buildMailAttachment));
+		const validAttachments = emailAttachments.filter((a): a is Mail.Attachment => Boolean(a));
+		if (validAttachments.length === 0) {
 			return;
 		}
 
-		const buffer = await FileUpload.getBuffer(file);
-		if (buffer) {
-			void sendEmail(
-				inbox,
-				{
-					to: room.email?.replyTo,
-					subject: room.email?.subject,
-					text: message?.attachments?.[0].description || '',
-					attachments: [
-						{
-							content: buffer,
-							contentType: file.type,
-							filename: file.name,
-						},
-					],
-					inReplyTo: Array.isArray(room.email?.thread) ? room.email?.thread[0] : room.email?.thread,
-					references: ([] as string[]).concat(room.email?.thread || []),
-				},
-				{
-					msgId: message._id,
-					sender: message.u.username,
-					rid: message.rid,
-				},
-			).then((info) => LivechatRooms.updateEmailThreadByRoomId(room._id, info.messageId));
-		}
+		const emailText =
+			message?.attachments
+				?.map((a) => a.description)
+				.filter(Boolean)
+				.join('\n\n') || '';
+
+		void sendEmail(
+			inbox,
+			{
+				to: room.email?.replyTo,
+				subject: room.email?.subject,
+				text: emailText,
+				attachments: validAttachments,
+				inReplyTo: Array.isArray(room.email?.thread) ? room.email?.thread[0] : room.email?.thread,
+				references: ([] as string[]).concat(room.email?.thread || []),
+			},
+			{
+				msgId: message._id,
+				sender: message.u.username,
+				rid: message.rid,
+			},
+		).then((info) => LivechatRooms.updateEmailThreadByRoomId(room._id, info.messageId));
 
 		await Messages.updateOne(
 			{ _id: message._id },
diff --git a/packages/model-typings/src/models/IBaseUploadsModel.ts b/packages/model-typings/src/models/IBaseUploadsModel.ts
index 332801dd50546..1161ab0fe86d9 100644
--- a/packages/model-typings/src/models/IBaseUploadsModel.ts
+++ b/packages/model-typings/src/models/IBaseUploadsModel.ts
@@ -10,6 +10,8 @@ export interface IBaseUploadsModel<T extends IUpload> extends IBaseModel<T> {
 
 	confirmTemporaryFile(fileId: string, userId: string): Promise<Document | UpdateResult> | undefined;
 
+	findByIds(_ids: string[], options?: FindOptions<T>): FindCursor<T>;
+
 	findOneByName(name: string, options?: { session?: ClientSession }): Promise<T | null>;
 
 	findOneByRoomId(rid: string): Promise<T | null>;
diff --git a/packages/models/src/models/BaseUploadModel.ts b/packages/models/src/models/BaseUploadModel.ts
index 77614d162d36e..ba4165534c00d 100644
--- a/packages/models/src/models/BaseUploadModel.ts
+++ b/packages/models/src/models/BaseUploadModel.ts
@@ -92,6 +92,16 @@ export abstract class BaseUploadModelRaw extends BaseRaw<T> implements IBaseUplo
 		return this.updateOne(filter, update);
 	}
 
+	findByIds(_ids: string[], options?: FindOptions<T>): FindCursor<T> {
+		const query = {
+			_id: {
+				$in: _ids,
+			},
+		};
+
+		return this.find(query, options);
+	}
+
 	async findOneByName(name: string, options?: { session?: ClientSession }): Promise<T | null> {
 		return this.findOne<T>({ name }, { session: options?.session });
 	}