WinZip Courier 4.0 Review: Zip and Encrypt Email Attachments With No Extra Work

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How Often Do You Zip Files?

Boxshot of WinZip Courier 4.0

I still remember the days when I used to zip almost every file I had to avoid maxing out my storage capabilities. Hard drive space was at a premium – and don’t even let me get started talking about the dozens of floppy disks I was always carrying around. Those were most definitely not the good ol’ days.

Nowadays, though, storage is fairly cheap and abundant. I rarely worry about running out of space. When I do start to get close to my max, I just plunk down a few dollars and increase my cloud storage limits. In fact, there are generally only two reasons I zip files today – either because I’m sending them as email attachments or because I want to group several small files together before uploading to make it easier on the downloader. The first situation is, by far, the most common scenario.

I suppose that’s why I find WinZip Courier so useful. The software combines the steps of zipping and attaching files into one action. Also, if you’re emailing photos, it lets you throw in the additional step of resizing as a bonus. Plus, for the most part, it basically works like a plugin so you can do all of these things within your email client if you’re using Microsoft Outlook or various webmail services such as Yahoo! Mail, Hotmail or Gmail. Unfortunately, the application doesn’t support Mozilla Thunderbird – oh well, maybe someday?

How WinZip Courier Works

Once installed and set up to your specifications (more on that below), the process for zipping attachments with WinZip Courier is really not much different than simply attaching a file without zipping it. Start by choosing the option to add an attachment. Then, when Windows Explorer opens, select the file(s) you want to send – note that you can choose multiple files by holding down the Ctrl key.

In the lower left corner of the Windows Explorer window, you should see the WinZip Courier logo and a few more options to the right of that graphic. If you want to zip and/or encrypt the attachment, put a check in the appropriate boxes. Also, if you’re including images in the attachment and want to resize them, click the respective button and you’ll be given several options to choose from. Then, just click the Open button and the newly created zip file will be attached to your outgoing email.

The following image shows what the resulting email would look like in Microsoft Outlook.

I’ve found this to be a super easy tool to use when I want to archive older documents on my system. First, I make sure all the docs are in the same folder, and then I open up Gmail in my web browser. I use WinZip Courier’s functionality to quickly create a zipped file, attach it to the email with a short note explaining what the files are and send the message to myself. Then, whenever I want to retrieve the file, I just use Gmail’s search tools. 

Setting Up the Program

After you install WinZip Courier, it’s a good idea to check and modify the default configuration settings for the program before you actually try using it. Even if you don’t want to change any of the defaults, a quick click-through of the various setting options will give you an idea of how the application will behave for different situations.

The first thing to decide is if and when you want to use the free ZipSend service to transfer large files. With this option, your zipped collection of files is stored in the cloud instead of being added as an attachment to your email. Since many providers limit the file size of attachments that can be sent via email or place limitations on the amount of data that can be stored in an individual account, ZipSend can be quite useful.

If you plan to use ZipSend, create an account at first. Then, open the WinZip Courier configuration tool and adjust your ZipSend options. By default, the application will be set up to use ZipSend whenever the attachment is greater than 5 MB in size, but you can change this to whatever size you like – or you can elect to always use the service, not matter how big the zip file is. On the other hand, if you don’t want to be bothered with this option and always want to send zip files as true attachments, select the “Never” option here. This will also prevent the “Your attachments are too big!” warning from popping up in the future.

How Well Does ZipSend Work?

Once you have created a ZipSend account and adjusted your settings, using the service is fairly automatic. All you have to do is create the attachment as you normally would. Then, if the final zipped file is larger than your specified limit, a pop-up will appear and ask if you want to use ZipSend instead of attaching the file to your message. You can always choose to ignore the warning and send as an attachment despite its size.

The first time I used ZipSend, I did run into a slight hitch. Since I hadn’t set up the ZipSend account yet, I chose to sign up through the link provided in the warning message. That part was quick and easy – and only required a minimal amount of personal info. However, when I went back to my email message and tried to enter my account information, WinZip Courier didn’t recognize my ZipSend login details right away. I’m not quite sure what the problem was – it could have just been a small delay in recognizing the new account – but rebooting corrected the issue.

Also, while ZipSend has deeper integration with Microsoft Outlook, you may have to go through a couple of additional steps when using it to send links to cloud-stored attachments through other email services. When I tested it using a Gmail account, accessed through Google Chrome, the option to create the zip file using WinZip Courier and ZipSend worked fine, but the ZipSend link was not added to the email. Instead, I had to log in to ZipSend directly to grab that link and paste it in myself. However, that was still much quicker that my old method that required me to zip and upload the file separately.

Worth the Money? (4 out of 5)

WinZip Courier 4.0 is priced at $24.95 – about what you’d expect for a utility application of this type. There’s also a free trial available from the WinZip product page so you can give the software a try before shelling out any cash. The additional ZipSend integration is quite nice for Outlook users, but those who use webmail services like Gmail will probably find it a bit clunky. That’s not to say it isn’t useful – it’s just not nearly as seamless as WinZip Courier’s other capabilities.

Despite my less-than-enthusiastic thoughts about the ZipSend service, I’m very fond of WinZip Courier’s basic capabilities. It’s one of those types of programs that you start to use so often, you forget it’s there because it’s doing most of its work in the background. You don’t realize how much time and effort it’s saving you until you sit down at another machine that doesn’t have the app installed. But, then again, isn’t that the mark of good utility software?