Hi julie_1120,
Thank you for reaching out.
Yes, you may send multiple documents simultaneously for signature using Acrobat Sign. If you are using the Acrobat desktop application, you may use the Request Signature feature. Please refer to the steps suggested in the following help document: https://adobe.ly/3J5pdsb.
However, the file will arrive as a single file after it is signed. If you wish to keep the document separated when receiving the signed file, please refer to the steps suggested here to make the changes in the settings: https://adobe.ly/3J3xjBy. The option to change these settings is available only in Acrobat Sign business and enterprise-level service plans.
Feel free to let us know if you have any questions.
Thanks,
Meenakshi