Chased down a late payment for three weeks once. Awkward emails. Phone calls. The whole thing. Turned out the client never even got my invoice because it went to spam. A Word document attached to a Gmail.

That was the last time.

Good invoicing software fixes everything that sucks about getting paid. Professional invoices that don't end up in spam folders. Payment buttons that let clients pay in seconds. Automatic reminders so you never have to send another awkward follow-up. Tracking that shows exactly who owes what and when.

Here's what actually matters when picking one.

Why This Matters

Still sending invoices from Word? Here's what that costs you.

Word doc invoices get paid slower. No online payment button means clients have to write a check or do a bank transfer manually. That's friction. Friction means delays.

They also look amateur. Whether that matters to you depends on your clients, but first impressions count. A branded, professional invoice from a real system sends a different message than "invoice_final_v3.docx."

And chasing late payments manually? That's time you're not billing. Time you're not working. Time you're just... waiting and hoping.

The right tool costs maybe ten to thirty bucks monthly and saves you hours of admin every single month. Plus the faster payments alone usually cover the cost.

What Features Actually Matter

The stuff you need. Online payments accepting cards and bank transfers. Automatic reminders before and after due dates. Professional templates you can customize with your branding. Recurring invoices for retainer clients. Mobile app so you can send invoices from anywhere.

The stuff that's nice to have. Time tracking if you bill hourly. A client portal where they can see all their invoices. Proposals and estimates that convert to invoices. Multi-currency for international clients. Late fees that add automatically. Deposit requests upfront.

If a tool doesn't do the first list well, skip it. The second list is bonus.

The Tools Worth Looking At

FreshBooks

This is the one I point most people toward. Started as invoicing software before expanding into accounting, and it shows. The invoices look great. The payment experience is smooth. Clients compliment them sometimes which is weird but it happens.

Payment reminders work automatically. Set them once and stop thinking about it. No more awkward "just checking in on that invoice" emails.

Time tracking built in. Client portal where they can see everything and pay you. Multiple payment options so clients can pay however they want.

Seventeen bucks monthly gets you five clients. Thirty for fifty clients. Fifty-five for unlimited.

Invoice Ninja

Completely free and open source. You can self-host it if you're technical, or use their hosted version.

Full features despite costing nothing. Unlimited invoices and clients. Proposals and quotes. Recurring invoices. Time tracking. Client portal. If you know HTML and CSS you can customize invoice designs completely.

Free if you self-host. Ten bucks monthly for the Pro hosted version. Fourteen for Enterprise.

Best option if you're budget-conscious or want total control.

Bonsai

Combines contracts, proposals, and invoicing in one place. If you need clients to sign something before you invoice them, this streamlines everything.

Contract templates with e-signatures. Proposals that turn into contracts that turn into invoices. All connected. Automatic payment reminders. Time tracking that flows into invoicing. Even calculates your taxes.

Twenty-one bucks monthly to start. Thirty-two for the plan most freelancers want.

Makes sense if contracts are part of your workflow.

HoneyBook

Built for creatives who want to manage the whole client relationship. From first inquiry through final payment, everything flows together.

Beautiful proposals with service packages. Contracts and e-signatures. Invoicing with payment plans. Scheduling. Client questionnaires. Workflow automation that handles follow-ups.

Sixteen bucks monthly gets you started.

Not really accounting software. Pair with something else for bookkeeping. But for the client experience part? Really good.

PayPal Invoicing

If you already have PayPal Business, this is free and simple. Not fancy but it works.

Create invoices. Send reminders automatically. Accept PayPal and card payments. Track what's paid and what's not. Works on mobile.

No monthly fee. Just transaction fees when you get paid. Two point nine nine percent plus forty-nine cents.

Best if your needs are basic and you already use PayPal.

Square Invoices

Free invoicing that connects with Square's point of sale system. If you do any in-person work alongside remote stuff, this handles both.

Accept cards, bank transfers, Cash App. Recurring invoices. Customer directory. The Plus plan adds contracts with e-signatures.

Free with standard transaction fees. Twenty bucks monthly for Plus.

Good if you mix remote and in-person work.

Zoho Invoice

Professional invoicing at competitive prices. Part of the bigger Zoho ecosystem so it plays nice with their other products.

Time tracking. Multiple payment gateways. Client portal. Multi-currency. Multi-language. Workflow automation.

Free tier exists with limits. Paid plans start at nine bucks monthly.

Best value if you want professional features without FreshBooks pricing.

Harvest

Primarily a time tracking tool with solid invoicing built in. If you bill hourly and tracking time accurately is critical, this is the one.

Excellent timers that run while you work. Turn tracked time into invoices automatically. Team features if you have people working for you. Expense tracking. Detailed project reports.

Free for one person and two projects. Twelve bucks monthly per seat for Pro.

Makes sense if time tracking is your main thing.

Getting Paid Faster

The payment methods you offer matter. Card payments happen twice as fast as check payments. Bank transfers are somewhere in between.

FreshBooks connects with Stripe, PayPal, and does bank transfers directly. Invoice Ninja supports over forty payment gateways. Bonsai and HoneyBook use Stripe. PayPal is PayPal. Square is Square plus Cash App. Zoho connects with most major gateways. Harvest uses Stripe and PayPal.

Transaction fees run around two point nine percent plus thirty cents for card payments. Stripe's bank transfer option is cheaper at zero point eight percent with a five dollar cap. PayPal is slightly more expensive at two point nine nine percent plus forty-nine cents.

The automation stuff saves hours. Set up payment reminders to go out three days before due, on the due date, and a week after if they haven't paid. Most tools let you customize the tone and frequency. Some escalate automatically with firmer language the longer they wait.

Recurring invoices work great for retainer clients. Set it up once, sends automatically every month. Some tools can even auto-charge saved payment methods.

Late fees can add automatically if you set them up. Either percentage-based like one point five percent monthly or flat fees like twenty-five bucks. Clients pay faster when they know there's a penalty. See our payment terms guide for more details.

International Clients

If you work with people in other countries, multi-currency invoicing matters.

Invoice Ninja supports over ninety currencies with automatic exchange rates. Zoho does one hundred eighty plus with multi-currency reports. FreshBooks lets you bill in any currency and set client-specific defaults. Xero has the most advanced multi-currency accounting if you need that level of detail.

The key features you want. Invoice in whatever currency your client uses. Get paid in whatever currency you prefer. Exchange rates that update automatically. And if you're serious about accounting, tracking realized gains and losses from rate changes.

Questions

Frequently Asked Questions

Wave and Invoice Ninja. Wave is unlimited free invoicing with no monthly fee. You only pay transaction fees when accepting online payments. Invoice Ninja is open source and free forever. Their paid hosted version is there for convenience but you don't need it.
You set rules. Reminder three days before due date. Follow-up a week after if still unpaid. The software emails your clients automatically with whatever message you write. Most let you customize how often, what tone, and whether to mention late fees.
If you use separate tools for each, yes. Integration kills double-entry and keeps everything accurate. All-in-one tools like FreshBooks or QuickBooks have it built in already. For standalone invoicing tools, check their integrations list for your accounting software.
At minimum card and bank transfer. That covers ninety-five percent of clients. Add PayPal if your clients prefer it. For international clients, offer Wise or multi-currency options. More payment options means faster payment.
Enable online payments. Cards get paid twice as fast as checks. Send invoices the moment you finish work. Automatic reminders help. Consider early payment discounts like two percent off if paid within ten days. Make the payment button obvious.
Your business name and contact info. Client name and contact. Invoice number that's unique. Invoice date and when it's due. Every service itemized with descriptions and amounts. The total. Payment instructions. Optional but smart: your payment terms, late fee policy, and a thank you.

My Picks

Most people should use FreshBooks. Professional invoices, fast payments, good experience all around.

Need free? Invoice Ninja. Full features, zero cost.

Contracts important? Bonsai. Contracts, proposals, and invoicing all connected.

Creative work with client relationships? HoneyBook. Beautiful client experience.

Bill hourly? Harvest. Time tracking built for invoicing.

Pick based on what matters most to you. The right tool pays for itself pretty fast.