The best invoice app for freelancers comes down to one question: which tool fits how you bill, and what keeps your books straight once the money arrives? The shortlist worth comparing is FreshBooks, Wave, Invoice Ninja, Bonsai, and PennyBot. The first four are invoicing-first tools. PennyBot is the odd one out: it is AI bookkeeping built for freelancers (not SMB teams with a controller on staff), and it does not create, send, or collect invoices at all. It is the bookkeeping side that pairs with whichever invoicing tool you pick: it takes in your bank transactions through the AI you already use (in the US, ChatGPT or Grok with your bank linked there) or a CSV or statement upload, categorizes expenses, and records each client payment as income.
Last updated: August 2026
The shortlist at a glance
Four of these tools cover almost every freelancer's invoicing situation, from "I just need a free way to bill three clients" to "I want contracts and invoices together." The fifth, PennyBot, covers the bookkeeping side. Here is who each one is for.
| Tool | Best for | Invoicing and expenses in one app? |
|---|---|---|
| PennyBot | Freelancers who want bank transactions brought in through their AI, expense categorization, and reports next to their invoicing tool | No: bookkeeping only, no invoicing |
| FreshBooks | Freelancers who invoice constantly and want a polished client experience | Invoicing-first, pair with a separate books tool |
| Wave | Brand-new freelancers who need free basic invoicing | Invoicing yes, no bank-feed categorization |
| Invoice Ninja | Freelancers who want a free or self-hosted, open-source option | Invoicing-focused |
| Bonsai | Freelancers who want contracts and proposals bundled with invoicing | Invoicing plus contracts, not full bookkeeping |
The honest summary: if invoicing is the only job you need done, a dedicated tool will do it well. If invoicing is one of several money chores (expenses, categorization, taxes, mileage), the case for pairing it with a bookkeeping app that handles the rest gets strong fast.
How the invoice apps compare on features
The core invoicing features are similar across the four invoicing tools; PennyBot has none of them. Where they diverge is everything that happens after the invoice is sent: whether the payment ends up in your books without retyping, and whether the same app also watches your spending.
| Feature | PennyBot | FreshBooks | Wave | Invoice Ninja | Bonsai |
|---|---|---|---|---|---|
| Send invoices (line items, multi-currency, payment terms like Net 15/30/60) | No | Yes | Yes | Yes | Yes |
| Auto-send and payment reminders | No | Yes | Yes | Yes | Yes |
| Card and ACH payment collection | No | Yes | Yes | Yes | Yes |
| Recurring invoices, saved templates, client portal | No | Generally yes | Generally yes | Generally yes | Generally yes |
| Bank transaction categorization | Yes, through your AI (ChatGPT, Grok) or statement/CSV upload | Not its focus | No | Not its focus | Not its focus |
| AI tax categorization | Yes | Not its focus | No | Not its focus | Not its focus |
| Mileage tracking | Yes | Not its focus | No | Not its focus | Not its focus |
| Starting price (as of writing) | $5/mo | about $17/mo | Free (basic) | Free / open-source option | See vendor |
| Invoicing available on | Not offered on any plan | Its paid plans | Free | Free / self-hosted | Its plans |
A few notes on that table, because the details matter. Wave is genuinely free for basic invoicing, which is hard to argue with, but it does not categorize from a bank feed and has no mileage tracking, so it stops short of being a bookkeeping tool. FreshBooks starts at about $17/month as of writing and is the most polished client-facing option of the group. Invoice Ninja has a free and open-source (self-hosted) option, which is unusual and appealing if you are technical. Bonsai bundles contracts and proposals alongside invoicing, which freelancers who send a lot of scope-of-work documents tend to like. Vendor pricing changes often, so confirm current numbers before you commit.
If you want a fuller accounting tool rather than an invoicing-first one, Xero is worth a mention: its Starter plan runs about $15/month as of writing, but it caps you at 20 invoices and 5 bills per month, which is tight for an active freelancer.
The row to read twice is the last one. PennyBot does not send invoices on any plan. It is a bookkeeping app, not an invoicing tool, and that is the single most important thing to know before you put it on an invoicing shortlist.
Why an invoicing tool still needs a bookkeeping app
Here is the workflow most freelancers end up with when they buy a dedicated invoicing tool: invoices go out from one app, expenses get tracked in a second app or a spreadsheet, and at tax time you reconcile the two by hand so they finally agree. That third step is pure overhead, and it is the one that quietly falls behind by month three.
A bookkeeping app that sees your bank transactions shrinks that step. When a client pays an invoice from your invoicing tool and the money reaches your bank, ask your AI to record your latest transactions in PennyBot (in the US, through ChatGPT or Grok with your bank linked there), or upload a CSV or statement, and the payment lands as income in the same books that categorize your spending. You still match a deposit to its invoice in your invoicing tool, but income in and expenses out live in one place, so your profit number is a real figure you can trust at any moment, not something you assemble later.
That advantage compounds for freelancers specifically, because freelancers wear every hat themselves. A few examples:
- Income is captured with everything else. Client payments come in alongside your spending when your bank transactions are recorded, with no separate income spreadsheet to keep. Our guide to a freelance income tracking app covers what that view should show you.
- Deductions are captured as you go, not reconstructed in April. A bookkeeping app that takes in your bank transactions categorizes each expense as it's recorded, which is the whole point of an expense tracking app for tax deductions. An invoicing-only tool cannot do this because it never sees your spending.
- Your business money stays separate from your personal money automatically. If your business income and expenses all run through the same bookkeeping app, the boundary is enforced by the system, which is far easier than the manual discipline described in separating personal and business finances.
A dedicated invoicing tool is a good screwdriver. The problem is that freelance finance needs a whole toolbox, and the invoicing tool is only one piece of it.
What PennyBot does not do
An honest comparison has to name the gaps, and for invoicing PennyBot's gap is total. It does not create, send, or collect invoices. There are no client pay links, no automatic payment reminders, no list of unpaid invoices, and no accounts receivable aging report. Recurring invoices, saved templates, and a client portal are not there either.
So the honest rule of thumb is this. Pick your invoicing tool on its own merits: FreshBooks or Bonsai if you run recurring retainers, want templated invoices, or need a polished client portal, and Wave or Invoice Ninja if your needs are simple. Then, if you want the money tracked correctly once it arrives, add PennyBot as the bookkeeping side. Knowing what is safe to spend once that income lands is a separate skill worth building either way, which we cover in freelance cash flow management.
Pricing: no plan includes invoicing
PennyBot has exactly two plans, and neither includes invoicing.
| Plan | Price (as of writing) | Invoicing included? |
|---|---|---|
| Essentials | $5/month | No |
| Professional | $15/month | No |
If you sign up expecting to send invoices, you will not find that feature on any tier. So the mental model is simple: every plan is for tracking your money, and your invoicing tool is where you bill for it.
The bottom line
The best invoice app for freelancers is the one that fits how you actually work. If you want recurring invoices, saved templates, or a client portal, a dedicated tool like FreshBooks or Bonsai is a fair choice, and Wave is hard to beat on price if your needs are simple. PennyBot is not an invoice app. It is the bookkeeping app that sits next to one: keep your invoicing tool, and PennyBot records each payment as income once your bank transactions are in, in the same books that track your expenses and mileage.
Just go in knowing that: no PennyBot plan sends invoices. If the bookkeeping side is what you need, See plan pricing to compare both plans side by side.
One honest note: PennyBot organizes your income and expenses, it does not give tax or legal advice, and no specific deduction or refund is guaranteed. For anything specific to your situation, that is a conversation for a tax professional.
Frequently Asked Questions
Which plan do I need to send invoices in PennyBot? None. PennyBot doesn't send invoices on any plan. Keep your invoicing tool, and PennyBot records each payment as income once your bank transactions are in PennyBot: through ChatGPT or Grok with your bank linked there (in the US), a CSV import, or a statement PDF on Professional.
Does PennyBot support recurring invoices? No. PennyBot doesn't create invoices at all, recurring or one-off. If you bill the same retainer every month, use an invoicing tool that automates recurring invoices.
Can PennyBot collect card and ACH payments on invoices? No. PennyBot has no invoices or pay links, so it doesn't collect payments. Your invoicing tool or payment processor handles that. Once that payment is in your bank transactions and they're in PennyBot, it's recorded as income.
Is a free tool like Wave or Invoice Ninja good enough? For invoicing alone, often yes. Wave is free for basic invoicing and Invoice Ninja has a free, open-source option. The tradeoff is that they are invoicing tools, not bookkeeping apps, so they will not categorize expenses from your bank feed or track mileage. You would pair them with a separate bookkeeping app for that side.
Do I still need a separate invoicing tool if my bookkeeping app handles invoices? Not necessarily. When invoicing and expense tracking live in the same app, the invoice you send and the income it produces stay connected, so there is nothing to reconcile between two disconnected tools at tax time. PennyBot doesn't handle invoices, though, so with PennyBot you keep a separate invoicing tool.
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