Modern Attachment Collection for High-Stakes Regulatory Matters

The Challenge

A global telecommunications company faced a complex regulatory matter requiring the rapid, defensible collection and production of Microsoft 365 data. A core challenge was the handling of modern attachments, also called linked documents, which are documents shared as links rather than traditional email attachments.

Linked documents introduce significant risk in regulatory matters. Linked documents may change over time, lose their connection to parent messages, or be produced without sufficient context. Out-of-the-box tools alone often fail to preserve version history or defensible relationships between messages and linked content, creating compliance and credibility concerns.

The client required a solution that would:

• Preserve the correct version of linked documents
• Avoid large, disorganized “data dumps”
• Maintain defensible relationships between messages and documents
• Withstand scrutiny from regulators
• Be executed on an aggressive timeline

The Cimplifi Approach

Cimplifi, a System One company, led the design and execution of a custom modern attachment workflow, built specifically to address the limitations of standard Microsoft 365 collection tools.

Rather than treating linked documents as traditional attachments, Cimplifi applied deep platform knowledge to recognize modern attachments for what they are: links to dynamic cloud-based content. From there, Cimplifi designed a workflow that balanced technical rigor with legal defensibility.

Key elements included:

• Strategic decision-making around when to link documents and when not to, based on the reliability of available metadata
• Custom scripting and process design layered on top of standard tools to close known platform gaps
• Clear, defensible processing rules aligned with regulatory expectations rather than convenience

The Outcome

• A regulator-ready production that addressed linked document risks head-on
• Clear preservation of document context and version history
• Reduced review complexity by eliminating unnecessary loose files
• A scalable workflow that can be reused across future matters

Most importantly, the client gained confidence that their most complex Microsoft 365 data was handled with precision, transparency, and defensibility.

The Solution: A Defensible Modern Attachment Workflow

Intelligent Collection Strategy

Cimplifi prioritized platform native collection where possible, while designing fallback workflows when Microsoft metadata proved incomplete. Linked documents were collected intentionally, not blindly, to ensure accuracy and defensibility.

Version Preservation

Rather than collecting multiple versions of a linked document, the workflow was configured to capture only the version closest to the time the email was sent or received.

This approach ensures case teams obtain the most accurate representation of the document as it existed when it was shared. This method effectively preserves the version that was linked at the time of the communication.

Purpose-Built Processing Paths

Cimplifi separated data by source and relationship type (email, Teams, OneDrive, SharePoint) using clearly defined processing tracks. This prevented commingling of unrelated data and allowed review teams to quickly understand context.

Defensible Linking (Without Over-Linking)

Where metadata supported it, Cimplifi preserved parent child relationships between messages and linked documents. Where it did not, documents remained searchable and organized without forcing artificial connections, reducing downstream risk.

Why Cimplifi

This matter demonstrates what sets Cimplifi apart:

• Leadership, not just tooling: Cimplifi does not rely solely on vendor defaults, we design workflows where platforms fall short.
• Deep technical expertise: Our team understands the realities of modern cloud data and how regulators expect it to be handled.
• Defensibility first: Every decision is grounded in what can be explained, defended, and repeated.