I tested Google Drive’s new AI cleanup tool on 14 years of clutter

I‘m an Apple person through and through. I’ve carried an iPhone since 2007 and owned a Mac even before that, so naturally I’ve been a loyal iCloud Photos and iCloud Drive user for years. My monthly $10 goes toward the 2TB iCloud+ plan because I have 488GB of data sitting there, including nearly 40,000 photos. Don’t judge. The real issue is that I’m also heavily invested in Google’s ecosystem, specifically Workspace apps.

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After 14 years of using Google Drive, I’ve accumulated 340GB of data from countless Google Docs, Sheets, Slides, and Gmail messages, plus file uploads. That’s why I shell out $20 a month for Google AI Pro, which gives me 5TB of storage and access to Gemini AI. And because apparently I need every subscription under the sun, I also pay $20 a month for ChatGPT Plus.

I need to cut subscriptions

I know. I really need to trim my subscription costs somewhere. I’ve debated whether to cancel ChatGPT or somehow reduce my Google usage enough to stop paying for extra Drive storage. Realistically, I don’t think I could ever get my data down to the 15GB Google gives me for free. My Drive has become so overwhelming that I’ve mostly stopped trying to manage it.

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The funny thing is that I’m hyper-organized in other areas of my life. My pantry features coordinated glass jars with labels. My daughter’s toy room has a designated spot for everything. My Google Drive, though? It’s a dumping ground. What can I say? Pre-parenthood Elyse wasn’t so organized.

Because my Drive has never been in great shape, I’ve let files, photos, screenshots, PDFs, tax documents, drafts, downloads, and random digital debris pile up with no real oversight for years. I keep putting off cleaning it.

Recently, I had the idea that some AI service could connect to my Drive and help me quickly organize it with a few clicks. Then I remembered my Drive contains things like my house deed, a copy of my will, and my LLC business details. Suddenly, giving a random third-party company broad access to my personal data felt like too much to handle.

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So here we are. My Drive is still a mess, and my subscriptions are still multiplying. Joy. I sure do love that in this economy.

Can ‘Organize My Files’ declutter my Drive?

But today I noticed a quiet little launch from Google: its Organize My Files feature is now available. Can Gemini actually, truly help me declutter, organize, and simplify my Drive now? Apparently, it uses Gemini AI to suggest moving loose files in Drive into existing folders or creating new folders for related files. And I get to review everything before anything moves.

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If this works, maybe one day I can move my data out of Drive and cancel my Google AI Pro plan for good. Maybe. One day.

How Organize My Files works

What you’ll need: A Google account with a messy Drive. Oh, and Google’s Organize My Files feature is currently limited to Google Workspace and Google AI subscribers. Workspace smart features must also be enabled for it to appear in Drive.

1. Click Suggest File Moves. Look toward the top of the file and folder list in My Drive for a new button called Suggest File Moves. Google said it will appear in My Drive as well as in parent folders in Drive. Clicking Suggest File Moves opens a new Organize My Files window, where Gemini will begin analyzing loose files and suggesting ways to clean them up. Also: This Gemini setting made my AI results way more personal Show more
2. Review Gemini’s suggestions. After a minute or so, Gemini serves up recommendations to review. They’re divided into two main types: Gemini may suggest moving files into existing folders in Drive. Gemini may suggest creating new folders for related groups of files. All files and folders can be previewed through hovercards or opened in a new tab for a closer look. Also: Is Google’s AI Ultra plan worth $100/month? Show more
3. Approve the changes. Use the checkboxes to select or deselect any file or folder that Gemini served up. Also, if a suggested folder name is weird, just rename it. Check destinations for folders, too. If they aren’t right, change the target. Once the suggestions look right and you’re happy, approve the changes. Gemini will then perform the file or folder moves in one batch and return to My Drive. Also: I used Nano Banana 2 to make perfect sketchnotes: 5 lessons Show moreMy resultAfter all that, Gemini suggested 19 moves for me. Nineteen. And it mostly surfaced recent files I had created or uploaded.Some of the suggestions made sense. Gemini wanted to move my resume and a couple of resumes I had helped family members create into an existing resume folder. It also suggested creating a new Family and Real Estate folder for house deed documents, plus a Travel Planning folder for upcoming summer trip itineraries I have stored in Drive. But one of the files it grouped under Travel Planning was literally called “Delete,” because it’s a doc I want to delete. Gemini did not realize that, nor did it suggest deleting it.To be clear, I have hundreds of gigabytes of data and years of clutter sitting in potentially thousands of folders in Google Drive.Also: How I unlocked another 15GB of Gmail storage for freeStill, I approved the changes Gemini recommended. For the heck of it, I ran the tool again. In about 30 seconds, it suggested the same thing: the same file moves, the same new folders, and the same changes it had just made. Weird. This feels half-baked.It’s not the sweeping cleanup assistant for Drive I was hoping for and need. Maybe it will get better over time. It did just come out of beta, and it’s possible Google will improve how Gemini scans Drive, prioritizes older files, recognizes obvious trash, and surfaces deeper organization tips. I just don’t want to do this in 1,000 different parent folders and hope it finds something new each time.Looks like I’m still stuck with a messy Drive and a $20 AI Pro subscription… for now.