Hightail Reviews in June 2026: User Ratings, Pros & Cons

It has size limits but it's useful tool for sharing files

PROS & CONS What are the best aspects of this product? I use this solution weekly as a work-around for clients that have some limits on size email they receive. We are able to send large files and photos that cannot be send otherwise. It is simple, intuitive and easy to use tool, it provides link for download and your job is done. What aspects are problematic or could work better? I’m using its free version but I still think that limit of 250MB for a file is sufficient size to make most ...

Secure solution for sharing large files with my customers

PROS & CONS What are the best aspects of this product? I have found this tool highly useful especially when I have to send secure files or too large files. I like that I can upload files and share them with my customers in more secure way with password included. I like the ability to see how long files remain available for download. What aspects are problematic or could work better? It would be great if they could include an interactive calendar that would show dates files when they are ...

It works well with Outlook

PROS & CONS What are the best aspects of this product? In handling large files, Hightail offers the right platform. It integrates well with Outlook, which means you do not have to switch to another screen when transferring files. The set up and administration is easy, which adds to its simplicity. You can manage users by either adding them or deleting them from your account and thus portrays a professional look. What aspects are problematic or could work better? The name can be hard to ...

Secure file and documents transfer

PROS & CONS What are the best aspects of this product? It allows for easy update of files for our clients. Where file transfer is involved and you are running a business, you need to be confidential by investing in a secure tool. Hightail offers that security and confidential for the files we send and receive. It keeps everything organized giving our business the needed boost. What aspects are problematic or could work better? The software crashes, at times, which can be annoying and ...

No project delays due to the ease of use

PROS & CONS What are the best aspects of this product? The ease of use of the tool makes it reliable to all our customers. Since we are involved in sending and receiving files from clients, Hightail has become a key figure in our work. It gives a professional look as we can transfer files and know when the customer has clicked on the link to the file. What aspects are problematic or could work better? When you look at the design of Hightail and compare it with that of Dropbox, it is not ...

Easy sharing of files without flooding the email server

PROS & CONS What are the best aspects of this product? It integrates or brings together multiple files, automatically, for fast download and upload durations. You can customize them according to your needs and end user experience. It has an attractive and detailed Dashboard, which is organized to help you get acquainted with the system faster. What aspects are problematic or could work better? It is impossible to redirect uploads to the admin and thus bugs in the operation of the ...

HIGHTAIL ARE STILL CHARGING for subscription cancelled 3 years ago!!!!

I cancelled my subscription for the file transfer service HIGHTAIL in October 2014 (!) and they are still charging my creditcard despite the fact that HIGHTAIL confirmed the cancellation by e-mail. I now have to go through the process of getting the money back via the credit card company. This is completely unacceptable! I have tried to find an e-mail address on their website, so I could inform them of this - but this seems virtually impossible - I can only find an address for "sales" and ...

Great Service

We are using this service over two years without any problem. I can set IP address for any major city from US, CANADA, UK, AUSTRALIA etc.

Scammy auto renew practices

I fell for their 'free trial'. They put my account in auto renew, charged me hundreds of dollars even though I didn't use the service after the first day of the 'free trial' and then refused to refund me.