Sending file attachments in Outlook email from Sharepoint Document library

Question

I own financial planning firm where we have always used traditional folder system to organize client documents - client folder, subfolders for bank/investment accounts with subfolders by bank and account number and years. Plus lots of investment and insurance statements also organized in folder with subfolders, legal documents, contracts, etc.

We have to send a lot of client files by email attachments in Outlook. Now I am wanting to convert over to sharepoint and flat document filing system with metadata. However, in planning this I am running into the problem of easily attaching large numbers of files (2-20 files, usually pdfs), such as 12 months of bank statements for a client, using Outlook email as attachments. I see that there is an add-in called harmon.ie that seems to solve the problem, but it is expensive. i am relatively small business with 3 employees.

Should I switch to sharepoint document libraries to use flat filing sytem with metadata and less subfolders, or should i continue to use traditional folder system in One Drive?

Answer 1

The requested functionality is also available in modern SharePoint apps. See example.

Some of the apps offer additional functionality such as automatic extraction of email metadata (subject, sent date, attachment names, ...) during uploading. Some even offer advanced features such as viewing email attachments (pdf, docx, xlsx, ...) in the browser, viewing emails in a thread, detect duplicates (across the entire tenant), detect and highlight privacy & confidentiality terms, ...

The apps may also offer a lower number of minimum licenses and cheaper license costs.

Answer 2

Hi @Joe Oettel,  

Welcome to the Microsoft Q&A forum. 

Thank you for sharing those details; they help me understand the situation much better. Transitioning from a traditional folder structure to a SharePoint metadata-driven system is a significant shift in information architecture. It is understandable that the "attachment problem" in Outlook feels like a major hurdle, especially when your priority is maintaining the efficiency required for a small financial planning firm. 

You can achieve the organizational power of SharePoint without the friction of a cloud-only file picker or the expense of third-party add-ins. The most effective solution for a team of your size is using the "Add shortcut to OneDrive" feature. By selecting this option within your SharePoint library, the entire structure appears directly in your Windows File Explorer. When you need to attach 20+ PDFs to an Outlook email, you can simply use the "Browse this PC" option and select your files as you always have. This provides a seamless bridge between modern cloud storage and traditional desktop workflows. 

Regarding your filing system, a purely flat structure is often difficult to manage in a high-compliance environment. For a three-person team, a hybrid approach is highly recommended: 

• Maintain one folder per client: This keeps your File Explorer view clean and intuitive. 
• Implement metadata columns: Add some tags like "Document Type" and "Tax Year." This helps you to filter and find specific statements across your entire library in seconds. 
• Utilize version history: Unlike traditional folders, SharePoint provides a full audit trail of changes, which is vital for financial contracts and legal documents. 

To ensure a seamless transition, I recommend following Microsoft’s official best practices for adding shortcuts to shared folders in OneDrive, which will allow your staff to attach SharePoint files directly through the familiar Windows File Explorer.

This strategy offers the best of both worlds: the robust security and searchability of SharePoint with the familiar ease of use your staff expects. 

I hope this response has helped address your question. Please feel free to reply if you have any further questions; I would be happy to assist further. I am happy to provide further guidance to ensure your migration is both smooth and productive. 

Thank you for your patience and your understanding. I look forward to continuing the conversation.

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Answer 3

For the specific need of sending many files via Outlook, SharePoint document libraries work well without requiring a third‑party add‑in, and they also help avoid large attachments by using links instead of files.

Key points based on the described scenario:

1. Attaching from SharePoint/OneDrive in Outlook (no add‑in required)
   In the new Outlook and Outlook for Mac, files stored in OneDrive or SharePoint appear as cloud locations when attaching:
   • In new Outlook: use Attach File → choose from OneDrive or SharePoint locations. Outlook then lets sending either:
     • A link (recommended, keeps email small, centralizes the document), or
     • A copy of the file as a traditional attachment.
   • In Outlook for Mac: use Attach File → Browse Cloud Locations to pick files from OneDrive/SharePoint, or use Insert Hyperlink if there is a URL to a folder or file.
   This works with multiple files (e.g., 12 monthly statements) and does not require harmon.ie.
2. Handling large or blocked attachments
   When files are large or of a type Outlook might block, Microsoft guidance is to store them in OneDrive or SharePoint and send a link instead of attaching the file directly:
   • Upload the PDFs to a SharePoint document library (or OneDrive for Business).
   • In Outlook, insert them as links from those cloud locations. This avoids size limits and blocked attachment types and keeps a single source of truth.
3. SharePoint vs. OneDrive for the filing system
   The choice between a flat, metadata‑driven SharePoint library and a traditional folder structure in OneDrive is about information architecture, not about Outlook integration:
   • Outlook can attach from both OneDrive and SharePoint using the same Attach File → OneDrive/SharePoint experience.
   • For a firm‑wide, client‑centric repository (multiple staff, shared access, permissions, retention, and views by client/year/account), SharePoint document libraries are generally better suited than personal OneDrive folders.
   • With SharePoint, it is possible to:
     • Store documents in a flat or lightly‑nested structure.
     • Use metadata (Client, Account, Year, Document Type, etc.) and views instead of deep folder trees.
     • Still easily select multiple files and share them via Outlook as links.
4. Practical sending patterns for the firm
   A workable pattern without extra cost:
   • Store all client documents in SharePoint libraries (with metadata and views to replace complex folders).
   • When emailing:
     • From Outlook: Attach File → pick from OneDrive/SharePoint and choose Send a link (or Send a copy if absolutely required).
     • From SharePoint: open the document library, select multiple files, use Share/Copy link (permitted by context via SharePoint/OneDrive sharing guidance) and paste the link(s) into Outlook.
   • For very large sets of files, consider sharing a folder or a view (e.g., “Client X – 2024 Bank Statements”) via a single link instead of attaching 20 PDFs.

Given the business size and the need for structured, shared client records, a SharePoint document library with metadata is appropriate. Outlook already supports attaching and sharing files from SharePoint/OneDrive, so there is no technical need to stay with a traditional folder system in OneDrive solely for email‑attachment reasons.

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References:

• Add pictures or attach files to emails in Outlook
• Attach a file or folder to a message in Outlook for Mac
• Blocked attachments in Outlook
• Reduce attachment size to send large files with Outlook