Hightail

Pros

Hightail makes it easy for me to share large files and folders with people inside and outside my company. You can create "spaces" where all types of files can be stores, and links to this space can be shared with anyone.

Cons

Safari does not support folder uploads, but opening chrome and uploading folders to spaces that way made it simple. This was my only hangup with the service.

Pros

I like that you have a custom link through which your clients or anyone can upload large files to send to you. Likewise, you are able to send professional looking emails with links for your clients to download large files you send to them.

Cons

I was never really able to get the files I stored in the cloud to sync in my local computer drive, so I lost quite a bit of files. I found Hightail more pricier than it needs to be. They used to be great when they were YouSendIt, but once they merged with Hightail, I feel the quality of the product diminished a bit. I didn't like that they do not provide a file preview. So I have to download several photo files to find the picture I'm looking for.

Pros

You can set up a linked folder on your machine that syncs with Hightail. Back in the day (prior to August, 2017) this formed an ideal platform for disseminating content as you could grab download links and include them in your own communications.

Cons

Hightail has recently adopted a typical self-focused millennial mindset of tunnel-visioned genius: focusing on an increasingly narrow range of cool stuff and killing off highly practical features without pausing to think about the spectrum of their users. If the HT people have a favorite way of working, they think that everyone works just like they do. As of the most recent downgrade, it is no longer possible to copy download links for files. If you need to send a business email with multiple download links and other content, you're now out of luck, as the only option is to use Hightail's interface to send an email with one (concealed) link.
My needs include the ability to send multiple download links to my dealers and prospective dealers - everything from canned social media content to a range of literature and photos. If, for example, a dealer is setting up a website and needs logos, product shots and text files, I can no longer just send out an email with the links to the files on Hightail.
Overnight they have unthinkingly destroyed my once routine means of distributing a huge amount of content to our dealers and prospects across the U.S. In a single, narrow-mined stroke, the value of Hightail to my company has vanished overnight.
This was a totally brainless move. I suggest that people look for a better solution.

Pros

I really like the control you can have over sharing files. Prior to hightail we would just share dropbox links but they were not secure nor could you tell if someone had downloaded a file. Hightail solves those problems.

Cons

There isn't much to not like. I wish the teams pricing was a little lower but it's more than fair given it's alternatives.

Pros

I like that I can share large files with my clients on a piece of software that lives on my computer rather than using an online service where I upload the file via a web browser. I feel it is a more secure process when using an app as opposed to using a service such as WeTransfer. I consider the free version to be a great tool that is less troublesome than dropbox.

Cons

While I consider the free version to be a great tool, I do believe that the paid version is a bit on the expensive side for my level of use. I consistently use HighTail, but not enough to justify a monthly subscription. If I run into limits on what I can upload for free, I will then move to another free alternative that has less restritive file size limits such as WeTransfer.