CHALLENGE - I need a new document automation solution for Mac -- Replacement for HotDocs (Windows)


I need some high-level help. I have been a Mac user for a long time. Like @MacSparky, I am an attorney. I am also a recovering IT consultant/software developer/project manager and did that for 13 years before going to law school.

For about ten years, I have been using document automation software on Windows called HotDocs. I have created my own custom Word and PDF templates and a sophisticated design of the data needed to drive those templates. I have spent many man months on them over the years and they have served me well. But I really need a replacement. HotDocs is the main thing that is keeping me running Windows. Everything else I do is on the Mac.

I want to ditch HotDocs and Windows and go 100% Mac for my law firm. I don’t believe there is a single product that will do everything I need. I’m hoping the community here can help point me in the right direction–help me figure out what products will work together to form a complete solution for my clients my staff, and me.

Here are the biggest issues I have with HotDocs:

  • The software is Windows only
More if interested
  • The desktop version is long in the tooth

  • Their web-based solution has been in development for years and is terrible–it doesn’t even have feature parity with the desktop version

  • The software company has been purchased by a large company (Abacus) and they are jacking up the price a LOT (about 600%)

  • The future of the product is uncertain - Abacus is pushing people to a virtual desktop solution, which I have no interest in. I have spoken with VPs at the company and my confidence in the future of HotDocs as a standalone, affordable product for small law firms has not improved.

I’m looking for one or more products that can work together to replace what I do with HotDocs. Here are my thoughts/needs:

I am not opposed to using a combination of different systems/products/services. I’m not opposed to using AppleScript, Keyboard Maestro, TextExpander or the like. If I need to do Mac scripting/automation, I’m fine with that. But, I would prefer to keep the bulk of the system in the cloud. However, I don’t want to have to build/operate/maintain my own server(s).

I haven’t found any one product that fills the bill on the Mac/Web. Most tools I have seen just do mail merge. Some are really ugly and not something that I can make client-facing. I also need more than just text substitution. I need to build documents/forms that are smart.

The solution should ideally have a web-based forms/questionnaire-type system input of data. However, everything about the solution doesn’t necessarily need to run in the cloud. The forms/data backend needs to be password protected and secure. It needs to be able to support client-facing entry and editing with the ability to save progress and come back to it later. The forms need to be dynamic–changing the questions based on other answers. My staff and I then need to be able to access all data for all clients. The forms need to support look-ups, repeating fields without a pre-defined number of those fields, e-signature, and they needs to look professional. So far, Cognito Forms seems like a possible candidate for the forms piece, data access and storage, but not the document templates.

The system needs to output to Word, but if it can also deal with PDF documents (adding data to a PDF form as well as outputting PDF), that’s a big bonus. Documents need to be able to dynamically adjust by looping through repeating fields–some of that data might end up inline and some might end up in table format.

Document generation needs to be able to be scripted. This is not a simple mail merge system. My current forms use IF/THEN statements, text transformation, scripting, math, date calculations, loops through records. There are scripts that call other scripts. There are nested forms within forms as well.

If anyone can offer advice, I would greatly appreciate it. I feel like I have been spinning my wheels for a long time trying to figure out how to piece this together at a high level. I’m hoping that maybe you have seen products that could form a viable solution. Or maybe you can think about the same products in a different way than I have. Hopefully, we can find a solution that is less than the $60/user/month that Abacus wants for its fewer-features-than-the-desktop cloud offering.

Thank you in advance for any contributions to the discussion!


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That’s quite the challenge, and maybe the sort of thing you would engage in a procurement tender or engage a consultancy to direct. I honestly don’t think cobbling together an automation based solution here is the right approach. Having a system designed to do what you want is almost certainly what you need. Here’s the top three reasons why I think that.

  1. Security - reading between the lines, you need guarantees around that. The more bits and pieces you have that aren’t designed by someone whose job it is to do IT security. Building it yourself will inevitably lead to issues. Data breaches are not something that’s out of the news much these dfays and you don’t want to put your business and clients on the line over it.
  2. Support - you’ve worked in IT. Now you don’t, your an attorney. So who would actually do all the support and development the solution would require as your business needs change? You? If so, that’s probably a big mistake as you would end up being sucked into that rather than focusing on your core business.
  3. Cost Benefit - I’m going to assume that the return on investment for time in the legal profession is generally oriented to legal time being financially very valuable. Assuming you can eventually identify a solution that you can buy off-the-shelf or engage someone to create for you that would meet your needs, then work out the value to your organisation. If there’s really nothing, consider a Mechanical Turk approach through temps or outsourcing.

In terms of what might be available, there are a couple of places I’d start for ideas to get a view of what’s available.

  1. Capterra - document generation software (list).
  2. Alternative To - Mac alternatives for ‘HotDocs document assembly’ (list).

If there’s nothing there, consider:

  1. Going through an IT procurement service/consultancy.
  2. Going out to tender for writing a bespoke solution.
  3. Sticking with what you have (for now), for all the costs and faults it sounds like it meets the minimum requirements, just not the nice to haves.
  4. Going with admin/clerical/temp staff.
  5. Going with outsourcing to another organisation or crowdsourced Mechanical Turk.

Hope something in that helps figure out what to look at next.


Thank you for the reply, @sylumer. Perhaps I didn’t do a good job of explaining. I would love nothing more than to buy something off the shelf. I just haven’t found anything that fills that need.

I don’t have the funds to have a system built for me from scratch.

So, I was hoping to find something accessible that I could use by utilizing two or maybe three products that would work together to form a complete solution.

I have seen those two sites you mention. But, it had been a while since I have looked at them. Checking again, I stumbled upon the open source project “docassemble”. It looks promising, but it isn’t there yet.

I appreciate what you are saying, but I’m looking at ways to try to cut costs and increase productivity. Going through a consulting firm or writing a custom solution is outside of my budget.

The reason I can’t (or at least don’t want to) stick with HotDocs is that it is essentially EOL. When I was paying $242 per year for maintenance and support, it was fine. But, now they want $60 per user per month. That’s $180 per month for me and my staff. Without updates, it could stop working at any time because it works through a MS Word add-in. I know this can happen because it has happened multiple times in the past. So, likely someday, Microsoft might release a patch for Office and break HotDocs in the process and then I will suddenly be out of luck.

Here, I’m not looking for someone to build the solution for me. I’m hoping someone can give me suggestions for a group of 2 or maybe 3 products that would work together (e.g. Cognito Forms plus Zapier, plus XXX), to form a replacement for HotDocs.