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Redline vs Square Invoices: what free actually covers.

Both have a free plan, and they cover different halves of the job. Redline's Free plan runs the front office by chat: contacts, the job pipeline, the calendar and quotes, for $0. Square Invoices' free plan sends invoices and takes payments. If billing is the only thing you need software for, Square's free plan does that and Redline's doesn't.

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The short version

Redline is chat-first field service software. On Free you tell it about the lead, it books the estimate visit, and it drafts the quote from your notes or a site photo. Invoices are not on Free. They start on Solo at $29 a month ($23 billed yearly), which adds card pay links on your own Stripe account with no Redline fee on top, deposits, overdue flags, expenses and profit per job.

Square Invoices is the invoicing side of Square's payments platform. It sends estimates customers approve online, e-sign contracts, deposits with a separate balance due date, and automatic payment reminders to the customer before, on or after the due date. Customers can pay by card, Apple Pay, Google Pay, Cash App Pay, ACH bank transfer or Afterpay. Square's contractor page pairs Invoices with separate Square products for appointments and staff.

Square's pricing page lists Square Free at $0 a month per location, with unlimited invoices, estimates and contracts; you pay processing fees when a customer pays, listed at 3.3% plus 30 cents online and 2.6% plus 15 cents in person on Free. Square Plus is listed at $49 a month per location, with lower processing rates (2.9% plus 30 cents online), milestone payment schedules, multi-package estimates, auto-converting accepted estimates to invoices and project tracking. Plus has a 30-day trial.

The part before the invoice

Any quotes still out?

Three, $9,840 total:

Kaplan, 200 amp panel upgrade, $4,300

Ferreira, EV charger circuit, $1,690

Abboud, basement lighting and outlets, $3,850

Draft a short follow-up to the Kaplans. Mention we can start the week of the 20th.

Here's the draft to Ruth Kaplan about the panel upgrade, with the week of the 20th as the start. Tap Approve & send on the draft to send it from your Gmail.

Quotes and Gmail drafts work on Free. Redline doesn't text, and it never emails a customer without your OK.

Redline and Square Invoices, side by side

	Redline	Square Invoices
How you use it	Chat first. You message it ("invoice Sullivan for the roof job") and it updates contacts, jobs, the calendar and invoices, asking you to confirm before it changes customer records. Web and iPhone.	Invoices, estimates and contracts from Square's dashboard and app, on Square's payments platform.
Free plan	Yes. $0 with no end date: AI chat, contacts, pipeline, calendar, scheduling assistant, Quick-Sort and a Pro Page. 1 seat and 4,000 AI credits that don't refill.	Yes. Square Free: unlimited invoices, estimates and contracts at $0 per location. You pay Square's processing fees when a customer pays.
Starting price	Solo at $29 a month, or $23 a month billed yearly. 7-day free trial on the web.	Square Plus at $49 a month per location, per its pricing page. 30-day trial.
Seats	Free and Solo: 1. Team ($129 a month): 3. Team+ ($299 a month): 10, plus extra seats at $29 each.	See their site. Staff management is a separate Square product.
Quotes	Itemized quotes by chat, including from a site photo, with an optional deposit %. Good, better and best options and tax are in the Quote composer (Solo and up). Saved as drafts; you email the customer from your own Gmail. No quote link, online approval or e-sign today.	Estimates customers approve online, plus e-sign contracts. Multi-package estimates and auto-convert to invoice on Plus.
Invoicing and payments	Solo and up. Branded card pay links on your own Stripe account, no Redline fee on top. Card only, US dollars. Overdue flags at day 3, 7 and 14.	On the free plan. Card, Apple Pay, Google Pay, Cash App Pay, ACH and Afterpay. Deposits and automatic customer reminders; milestone schedules on Plus.
Scheduling	Every plan. Suggests up to 3 open slots, groups visits in the same town, sets up repeating visits with one save. No calendar sync, no online booking.	Through Square Appointments, a separate Square product.
Dispatch	Team and up. Dispatch board, tech app, assign jobs by chat, crew chat. Techs tap their status; there's no GPS.	See their site.
What Square Invoices has that Redline doesn't	Not in Redline today.	Invoicing and payments on a free plan. Online estimate approval and e-sign contracts. ACH, wallets, Cash App Pay and Afterpay. Automatic payment reminders to customers. In-person payments.
What Redline has that Square Invoices doesn't	A job pipeline from Lead to Paid, a calendar with a scheduling assistant and quotes by chat, in one app on the Free plan. Crew dispatch on Team.	Square's contractor page pairs Invoices with separate Square products for scheduling and staff.

Square Invoices details come from Square Invoices' own website, checked October 2026. Plans and prices change, so confirm on their site before you decide.

Who should pick which

Pick Square Invoices if

You need to send invoices and get paid, and you want that free
Customers ask to pay by bank, Apple Pay, Cash App or Afterpay
You want customers to approve estimates and sign contracts online
You want payment reminders to go out to customers on their own
You already take in-person payments through Square

Pick Redline if

Leads and quotes slip through before they ever become invoices
You want the calendar, the pipeline and the paperwork in one app
You'd rather type "follow up with the Kaplans" than click through screens
You'll pay $29 a month for invoicing because the rest of the office matters more
You plan to add a helper and want a dispatch board later (Team)

Questions contractors ask

Is Redline free like Square Invoices?

Not for invoicing. Redline's Free plan covers the chat, contacts, pipeline, calendar, scheduling assistant and quotes, with no end date. Invoices and card pay links start on Solo at $29 a month. If free invoicing is the whole requirement, Square's free plan covers it and Redline's doesn't.

Can I use Redline Free and Square together?

Yes, as long as you're fine typing the invoice twice. Run leads, quotes and the calendar in Redline Free and bill in Square. Nothing connects the two, so the job total won't flow across on its own. When re-typing gets old, Solo lets you bill straight from the job.

How do customers pay a Redline invoice?

By card, on a branded pay link that runs on your own Stripe account. Redline adds no fee on top of Stripe's processing. It's card only today: no bank transfer, Cash App Pay or Afterpay. See invoicing.

Does Redline send payment reminders to customers?

No. Redline flags an unpaid invoice to you at day 3, 7 and 14 and tells you who to call. A reminder to the customer is an email it drafts and you approve. Square sends reminders to the customer automatically. See overdue invoice alerts and Square Invoices alternatives.

Use the free part for what it's good at.

Put your open quotes and next week's visits into Redline Free and see if the chat keeps them from going quiet.