What to file, what to watch, and how to stay ahead this month
May is a steadier month on the compliance calendar than April — no quarterly filings due, no Q1 scramble. But steady doesn't mean slow. Monthly filers still have deadlines to hit, nexus thresholds keep moving, and anything that slipped through April will only get more expensive if it sits another 30 days.
Week of April 28 – May 1
Reconcile April transaction data
Pull April reports from Shopify, Stripe, or your billing platform.
Check for regulatory changes to ensure that you’re compliant.
Flag and investigate any inconsistencies between tax collected and tax owed – go state by state.
Review nexus status
Did April revenue push you across any new state thresholds?
Ensure that you’re registered in any jurisdiction where you have nexus.
Not sure if you have tax exposure? Try our free Nexus study.
Week of May 5 – 9
Prepare monthly filings
Confirm your specific deadlines by state.
Ensure that you’re registered in the necessary states, and gather credentials for every state portal you need to file in.
Ensure that the tax you collected in the prior month is ready to go.
Respond to any outstanding state notices
Address anything that came in during April: nexus questionnaires, compliance letters, audit inquiries. The sooner you tackle these, the sooner you can get current.
Week of May 12 – 16
File monthly returns
Manual filing takes time: set aside several days in order to file accurately and without rushing.
In addition to state returns, make sure you’re tackling local jurisdictions, including city and county returns.
Save confirmation numbers for every filing.
Review exemption certificates
B2B sellers: check that exempt customer certificates are current and on file. Expired certificates mean you should have been collecting tax.
Not sure how to manage exemptions? Here’s our guide.
Week of May 19 – 23
Spot-check product taxability
Did you launch new products or SKUs in April?
Review taxability rules by category and state to avoid costly audits down the road.
Check Q2 nexus trajectory
You're nearly two months into Q2. Are you approaching thresholds in any new states?
If you're close, registering proactively is easier than registering under pressure.
Week of May 27 – 30
Start organizing for June
Monthly filers: begin pulling May data early for June filing.
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