Library
All guides
Every article on the site, grouped by topic. 33 guides so far.
Fundamentals
Start here
Authentication: why your password is not the fence you think it is
A password is a guess gate, not a fence. A practical guide to the layers that actually keep attackers out of your document accounts — multi-factor, hardware keys, passkeys, and the account-recovery flow almost everybody forgets about.
Level: beginner
Threat modeling for normal people
You can't defend your documents until you know who you're defending them from. A practical, low-jargon guide to writing your first threat model.
Level: beginner
The CIA triad, explained without jargon
Confidentiality, Integrity, Availability. Three words that define what 'secure' actually means — and why your document problem is usually just one of them.
Level: beginner
The copy problem: why digital documents multiply, and what that means for security
Paper sits in one place. Digital documents do not. Every edit, every sync, every backup, every preview makes another copy. Security thinking that treats a file as a singular object fails — here's how to think about it instead.
Level: beginner
What is metadata, and why it often leaks more than the file itself
You redacted the sensitive text in a Word document and sent the PDF. Turns out the Word document's tracked changes went with it. A practical tour of the metadata that rides along invisibly on the files you share.
Level: beginner
Security is a practice, not a product
Setting up MFA, encrypting your disk, and running a password manager once is not the end of the story. Accounts drift, software rots, vendors change. Here's what maintenance actually looks like — and the annual rituals that separate real security from a snapshot.
Level: beginner
The supply chain of trust behind every document you store
When you save a PDF to Drive, you're trusting more than Google. The full chain runs through your operating system, your browser, your network, certificate authorities, and every software update that touched your device. Learning to see it is the difference between reasoning about security and guessing.
Level: intermediate
Encryption
Scrambling data so only you can read it
Encryption at rest vs in transit: what the labels actually mean
The two phrases you see everywhere in cloud marketing, translated from vendor-speak into reality. Plus what each one protects you against, and what it does not.
Level: beginner
Full-disk encryption on every platform: what's on, what to turn on, and what it doesn't protect
BitLocker, FileVault, and LUKS in plain English. On modern consumer hardware, full-disk encryption is often already enabled — this article covers how to verify it, how to configure it properly, and what threats it genuinely protects against.
Level: beginner
End-to-end encryption, explained: what 'E2EE' actually means, and what it does not
E2EE is the gold standard for messaging and increasingly for document storage. It is also the most marketed and the most misunderstood. A working definition, and the questions to ask of any service that claims to offer it.
Level: intermediate
Tar, encrypt, upload: using GPG to secure files before they hit the cloud
A no-nonsense tutorial on using GnuPG to encrypt files before they leave your machine. Works with any cloud provider, requires no new service, and keeps you in control of the keys. Plus when this is the right tool and when it isn't.
Level: intermediate
Cloud storage
Google Drive, iCloud, OneDrive, Dropbox, and friends
What happens when you upload a file to the cloud
Drag-and-drop hides a remarkable amount of machinery. A plain-English tour of what actually happens to your file between your Desktop and a cloud provider's storage — and the moments in that journey where security matters most.
Level: beginner
Hardening Google Drive, iCloud, OneDrive, and Dropbox: a settings checklist
Every major cloud storage service has a handful of settings that determine whether your files stay yours. This article walks through the ones that actually matter on each of the big four providers, and why.
Level: beginner
How to read a cloud provider's security page like a skeptic
Every cloud service has a security page full of reassuring phrases. This is a practical guide to reading past the marketing and finding what the provider is actually telling you — and what it is not.
Level: intermediate
Client-side encryption on top of Dropbox and Drive: a Cryptomator walkthrough
You don't have to leave Google Drive, Dropbox, iCloud, or OneDrive to get end-to-end encryption for your most sensitive documents. Cryptomator lets you add an encryption layer on top, with the provider seeing only opaque blobs.
Level: intermediate
Privacy-first cloud providers: Proton Drive, Tresorit, and the tradeoffs
E2E encrypted cloud storage exists and has for years — it's not a new category. What's new is that it's become usable. A practical comparison of Proton Drive, Tresorit, and the usability tax you pay for end-to-end encryption by default.
Level: intermediate
Backups
So you never say "I had one copy"
Time Machine and Windows Backup: a household backup setup you can set up once
Every modern computer comes with built-in, reliable backup software. Most people never turn it on. A step-by-step setup for Time Machine (Mac) and File History / Windows Backup, plus what each one actually protects.
Level: beginner
The 3-2-1 backup rule, and why most people only have 1
Three copies, two media, one off-site. The rule is almost fifty years old and still undefeated. A practical guide to living it without paying for a full IT department.
Level: beginner
Cloud sync is not backup, and what to do instead
Dropbox, iCloud Drive, Google Drive, and OneDrive are synchronization services. If you delete a file, they delete the file. This article explains the difference that has cost more people their photos than any other single mistake.
Level: beginner
Testing your backups: the practice that separates real backups from wishful thinking
A backup that has never been restored from is a rumor. A practical guide to the 30-second quarterly test that catches failed backups while the house is not on fire — and the systemic tests that matter for small businesses.
Level: beginner
Sharing securely
Getting the file to the right person, no one else
Expiring links, access logs, and sending sensitive files to people who aren't technical
Most people you need to share a sensitive document with are not going to install a new app to receive it. Here's how to use the tools you already have — with the expiry, access logging, and revocation features turned on.
Level: beginner
Sharing sensitive documents with your accountant, lawyer, or doctor
You have to share tax returns, legal filings, and medical records with people who need them. Those people often aren't technical. A practical guide to sending sensitive documents to professionals — what's safe enough, what isn't, and how to push back when their workflow is insecure.
Level: beginner
Password-protected PDFs, done right
Password-protecting a PDF sounds simple, and most of the time it is done wrong in a way that offers almost no real protection. Here's how the feature actually works, and how to use it so it means something.
Level: intermediate
Sending documents by email without the email reading them
Email is the most insecure transport most people use every day. A practical guide to making it usably private — from the one-click options (ProtonMail-to-ProtonMail) through the real engineering (PGP, S/MIME) and the tradeoffs of each.
Level: intermediate
Destruction & disposal
Making a file really, truly gone
Retiring old laptops, phones, and drives without leaking your life
A checklist for selling, recycling, or handing down a device, so the next person gets the hardware and none of your history.
Level: beginner
Closing a cloud account without leaving data behind
Deleting an account is not one click; it's a procedure. A walkthrough for closing Google, Apple, Microsoft, and Dropbox accounts properly, including the cleanup most people skip — linked devices, shared content, recovery paths, and the things you'll never get back if you rush it.
Level: beginner
Paper documents and shredding: the often-forgotten side of secure disposal
Every security site talks about digital destruction. Your bank still sends paper statements, your health insurance still sends EOBs, and your tax records are still partly on paper. A practical guide to what to shred, which shredder to buy, and the standards that actually mean something.
Level: beginner
Why 'empty the trash' doesn't really delete your files, and what actually does
On modern operating systems, deleting a file just unlinks it. The data usually stays on disk until something else happens to write over it. A practical tour of how deletion really works — and the one reliable way to make a file unrecoverable.
Level: intermediate
Digital estate planning
Your documents outlive your devices
Small business & compliance
HIPAA, GDPR, and document retention
HIPAA for solo practitioners: the parts you actually need to understand
HIPAA is a big, scary-sounding law. For a one-person therapy practice, a solo chiropractor, or a small clinic, the parts that actually matter are a manageable set. This article walks through those parts in plain English.
Level: intermediate
GDPR for a very small business: the three things that will trip you up
GDPR applies to one-person businesses just as much as to Google. The good news: for most small operators, only a handful of obligations really matter day-to-day. This article covers them, in plain English, with the traps that catch small businesses most often.
Level: intermediate
Threats to documents
What you are actually defending against
Infostealers and the documents on your laptop
Infostealers are the most commercially successful category of malware of the last few years, and they are very specifically interested in your documents. This is what they do, how they get in, and how to make yourself a much less useful target.
Level: intermediate
Ransomware, from the perspective of your documents
Most ransomware advice is aimed at enterprise IT. The household and small-business version is shorter — and the most important defenses are not glamorous. A practical guide to how modern ransomware works and the specific steps that protect documents from it.
Level: intermediate