How Does Microsoft Copilot’s New OneDrive Connection Feature Really Work in Practice?

Can Microsoft Copilot Finally Access Personal Files Like a Real AI Assistant?

Microsoft has quietly introduced a game-changing feature that brings its AI assistant closer to being a truly personal helper. The Connected Apps functionality now allows Copilot to access and work with files stored in your OneDrive. But does it live up to expectations?

What Makes This Feature Different

For years, AI assistants like Cortana, Siri, and Google Assistant were little more than fancy search engines. They could answer basic questions but couldn’t truly understand your personal data or work with your documents.

Microsoft Copilot’s Connected Apps feature changes this by letting the AI:

• Open files directly from OneDrive by name
• Read and analyze document content
• Create summaries of lengthy reports
• Combine information from multiple files
• Generate new content based on your existing documents

How to Set Up Connected Apps

Setting up this feature is surprisingly simple, but there’s one important catch – it only works on Copilot web, not the desktop app.

Here’s how to enable it:

1. Visit Copilot web and sign in with your Microsoft account
2. Click your profile picture in the top right corner
3. Select your username again
4. Find “Connected apps” in the menu
5. Toggle on the OneDrive option

Important note: OneDrive is currently the only supported service, though the interface suggests Microsoft plans to add more connections soon.

Real-World Testing Results

When put to the test, Copilot showed impressive capabilities with some notable limitations:

What Works Well

• File Finding: Copilot successfully located documents even when given slightly incorrect names
• Content Analysis: It provided accurate summaries of long documents (tested with an 11,000-word dissertation)
• Smart Suggestions: The AI suggested related documents based on content keywords, not just filenames
• Follow-up Questions: Copilot maintained context and could answer specific questions about previously accessed files

Where It Struggles

• Data Accuracy: When combining information from multiple files, some details were incorrectly altered or made up
• Complex Tasks: Advanced operations requiring precise data extraction showed mixed results
• GPT-5 Integration: The premium “Smart” mode couldn’t consistently access OneDrive files during testing

How It Compares to Competitors

The testing revealed interesting differences between AI platforms:

• Microsoft Copilot: Successfully accessed OneDrive files and attempted complex multi-document tasks, though with some accuracy issues.
• ChatGPT: Despite having Connected Apps enabled for OneDrive, it failed to access files automatically and requested manual uploads instead.
• Google Gemini: Couldn’t complete similar tasks with Google Drive integration, even after multiple attempts.

This suggests Microsoft has taken an early lead in cloud storage integration, even if the execution isn’t perfect yet.

Storage Requirements and Limitations

To use this feature effectively, you’ll need adequate OneDrive storage. Microsoft offers:

• Free tier: 5GB (suitable only for basic documents like PDFs and Word files)
• Paid subscriptions: Include at least 1TB of storage

The feature works best when you already store your important documents in OneDrive rather than competing services like Google Drive or Dropbox.

What This Means for Your Productivity

For Microsoft 365 users, this feature represents a significant step toward truly personalized AI assistance. You can now:

• Quickly find and summarize meeting notes
• Create reports by combining data from multiple spreadsheets
• Draft social media posts based on existing research documents
• Get insights from project files without manually opening each one

However, it’s important to verify important details when Copilot combines information from multiple sources, as accuracy can vary.

Looking Ahead

Microsoft appears to be testing broader file access capabilities. When asked about local PC files, Copilot responded by requesting permission to read computer files, suggesting local file integration may be coming soon.

The Connected Apps feature also hints at a future where AI assistants can work seamlessly across all your digital documents and data sources, making them genuinely useful productivity tools rather than glorified search engines.

For now, if you’re already invested in the Microsoft ecosystem, this feature makes Copilot notably more practical for daily work tasks. Just remember to double-check the AI’s output when accuracy is critical to your work.