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.

Hi, Jonnie -

Not sure if you’ve found your document automation/assembly solution yet, but we’ve got one that integrates with all the form builders (Typeform, Jotform, Google Forms, and so forth) and can integrate with your CRM and other tech tools as well.

There’a free 14-day trial: Lawyers love how much easier it is to use than HotDocs (we’re a super friendly, customer-centric company, too!)

Hi Jonnie

It might be too late but maybe my answer will help others.

I tried for years to do what you want.

At the end, I have three possible outcomes :

  • automating with ActionStep - this is what we chose at the end, very practical and powerful, but we are very disappointed by the level of service (from slim to none, we had to wait 4 months (!) for a billing issue and we cannot afford that any longer) ;
  • automating with typinator (much more powerful than textexpander and does the job as you can do a lot when combining word styles and hotkeys with typinator) ;
  • Typeform -> Zapier -> Webmerge. Powerful but very timeconsuming to setup.

Tell me if you want to continue the discussion.

I’m also a lawyer and on the same hunt for the Holy Grail that @JonnieCache was on. I’m an associate in my firm but the only one working on a Mac. There seem to be far more document assembly solutions on Windows, for sure.

I’m currently using a self-made FileMaker solution to handle the tracking of contacts, matters, and invoicing. I can also do some very simple document assembly using the 360Works Scribe plug-in. I’m pretty happy with how I’ve got FileMaker to handle the practice management end of things, but I’d definitely love to find a better solution for document assembly – ideally one that could “connect” to FileMaker to grab the data that’s already in there.

Thanks to everyone for their replies and suggestions.

I have taken a look at ActionStep, Typinator (I’ve been using Text Expander), Woodpecker, and now 360Works Scribe.

My take on ActionStep, Woodpecker, and 360Works Scribe is that they are still dealing primarily with text replacement. Typinator (or Text Expander) work great for repetitive text, but not really the automation that I’m looking for.

I’ve just recently started working with XpressDox ( I hadn’t heard of it before, but it came up in discussions with the management at the state bar association. It has been around a long time, but is only recently starting to get a presence in the U.S. It’s based in South Africa. There is a US consulting group that is their primary distributor, Docugility ( I have spoken with Bethany Keaveny there and I think it has everything that HotDocs offers and more. I’m still getting my feet wet.

It’s reasonably priced. It seems to me to be even more powerful than HotDocs. It is web-based and hosted through MS Azure. (Docugility will set all that up for you.)

I’m still working on converting going through the conversion of my existing templates. I’ve been working with XpressDox support and they just gave me a new build to try the conversions with. They are still working to improve the automatic conversion. Simple templates convert fine. But, more complex templates not as well. Since most of my HotDocs templates are complex, so rather than hand-coding everything, I’ve been working with them on their conversion process.

The main downside that I see right now is that the templates must be created with Word for Windows. But, I can just do that with Parallels. Once the templates are in the cloud product, my staff can utilize them on the Mac.

Hello Jonnie,
I am also an attorney and have been using a MAC for a couple of years now. For the most part, it integrates fine with what I need to do, but I recently came up against the HotDocs issue that you have been discussing. I was considering subscribing to Lexis, but it requires HotDocs, which I can’t use on my MAC, so I would have to use my old laptop to run the HotDocs, then email myself my documents, which ends up nothing but a hot mess and not a time saver at all! Just wondering if you have any advice for me?

lawyer here. 31 years and counting. trials and litigation.

I’m near completion of building my own contacts manager in FM19, and just recently switched to DT for case management. I’ve tried all the shelf products over the years. they are terrible to not good. it occurred to me along the way a decade ago; separate contacts and case management into separate apps, and link them under the covers.

my goal is to;

  1. integrate printing solutions into the contacts manager, first. to do this, I’m going to first, automate some document creations using keyboard maestro, and go where that takes me.

I’ve built tables and the appropriate relationships in the CM to handle most legal printing needs as far as matters and clients go.

  1. my plan is to first build in FM a print layout with dropdown boxes to select, client, matter, then the type of document needed. [eg, a pleading or a letter].

unless I figure something better or get a tip, I’ll have the CM trigger maestro to create the doc in pages, drawing data from the CM.

IF this works, I’ll reduce the functions from dropdowns, to buttons where I can, and place them on a tab within the CM lead page per client. about reduction - if you’re already calling up a client and a matter, then half the info is already on the table, so no need to reselect it in a dropdown or elsewhere. but I digress. . .

I’ve built the CM where literally everything per client is in one layout, and the printing functions will be accessible on the same page, in tabs. this, in my opinion, is where shelf products fail. there are too many layouts among other things.

once I get this working, I’ll see what I can do to mimic the print functions in DT. I can probably rig the CM to call up what ever client/matter is viewed on DT and simply cheat like that. as a start, anyway.

I detest web solutions for these things. security isn’t the issue. lag, and functionality is.

anyway…its a tall order but I’m working on it.

would love to see more action on this thread.

EDIT: someone mentioned woodpecker. I tried it about a year ago. nope.