Updated on October 7, 2026 by Whole Technology
Start Early: November Is the Time
Tax season punishes firms with fragile IT. Slow servers, failed backups, and phishing attacks don’t wait until April — they hit in the middle of deadline week. Run through this checklist now so your 2027 tax season is boring in the best way.
The 2027 Tax Season IT Checklist
1. Backups: tested, not just scheduled
A backup you haven’t restored is a hope, not a plan. Verify that full and offsite backups of your tax software data, client files, and email actually complete — then do a test restore before January. If your firm is still backing up to a USB drive in a desk drawer, fix that first. (Related: Tax Season Is No Time for an IT Outage.)
2. Tax software performance under load
UltraTax, Lacerte, and ProSeries all slow down when every preparer is in the system at once. If your tax applications run on an aging office server, consider hosting them in the cloud — we moved one accounting firm’s UltraTax to Azure Virtual Desktop and their busy-season performance problems disappeared. Load-test before February, not during it.
3. Cybersecurity: lock down the obvious doors
Accounting firms are prime targets — you hold Social Security numbers, bank details, and tax returns. At minimum, confirm: multi-factor authentication on email and remote access, current endpoint protection on every workstation, encrypted email for client documents, and a firewall with active threat monitoring. Our free 27-point IT & security assessment covers all of these.
4. Phishing training before W-2 season
January brings a flood of W-2 phishing scams aimed directly at accounting staff. Run a short refresher with your team: verify unexpected payroll or direct-deposit change requests by phone, hover before you click, and report anything odd immediately. One trained employee stops the attack the firewall misses.
5. Remote and hybrid access
If staff work from home during busy season, their remote connections need to be fast, secure, and reliable. Test VPN or virtual desktop performance from home networks now. Make sure remote workers have a clear way to reach support when something breaks at 9 PM on a deadline night.
6. Printers, scanners, and e-filing
Nothing derails an April afternoon like a dead scanner. Service or replace aging printers and scanners in December. Confirm e-filing credentials and software updates are current so you’re not troubleshooting logins on deadline day.
7. Phones and internet redundancy
Clients call constantly during tax season. If your internet goes down, do calls go with it? Confirm you have a failover option — a backup connection or phones that keep working independently — and that your number can ring to staff mobiles in a pinch.
8. A support plan with teeth
Who do you call when the server crashes on April 14th? “Our IT guy” isn’t a plan if he’s on vacation. Make sure you have guaranteed response times in writing — ideally from a team that already knows your systems, not someone learning them during your emergency.
Don’t Wait Until January
Every item on this list is cheaper and calmer to handle in November than in March. Start with the free assessment — we’ll tell you exactly where your firm stands before busy season does.
Get My Free 27-Point IT & Security Assessment
