Things I Don’t Like About File Upload Plugins in 2025

Why They Still Cause Headaches. Is it possible to fix them?

Key Takeaways

• File upload issues have persisted from the punch card era to the cloud days.
• Many plugin problems can be solved with server configuration changes.
• The best solutions combine user-friendly interfaces with back-end handling.
• Professional tools and APIs can help
• Choosing the right one requires balancing budget, performance.

Introduction

We are in 2025, and the internet has been around for over 50 years. Yet, some of the frustrations we have with it remain the same.

If you take a quick look at the web developer subreddit forums on Reddit, you’ll find some of them complaining about how difficult it is to integrate a file upload plugin into a web application.

One Reddit user recently complained that the file upload plugin he’s using on a WordPress site is “going to drive me crazy.”

The JavaScript expert said he has about 50 products with upload issues. One of them requires documents to be downloaded in a specific file type because of the specific template it requires.

🔗 See the Reddit thread here

Another Reddit user is more direct: How do I have a file upload system without a plugin? He says he needs to make routine code changes because of WordPress updates.

🔗 Reddit discussion on avoiding plugins

On Medium, an expert says that as an independent developer, one of the most tedious parts is integrating the file upload widget into client projects.

🔗 Medium article on adding upload widgets

On StackOverflow, a programmer says his jQuery file upload plugin doesn’t work.

🔗 StackOverflow question on broken jQuery uploads

A Historical Perspective: Human–Machine Interaction

Since my earliest experiences as a computer user, this file upload issue has always been one of the most disappointing in terms of user experience. To understand why, it helps to look at the long history of how humans input information into machines.

Let’s put this issue into perspective to understand the context surrounding file uploads. Within the field of programming, this topic revolves around the interaction between humans and machines.

Since the creation of the first computing devices, the way information is input into the machine has been the starting point of the process. Every diagram of how a computer works shows that the first step is when the user inputs information.

Early adopters in the 1940s and 1950s used punch cards to input data into the computing machine.

At the same time that the development of commercial computing devices began to utilize screen displays (originally televisions), input began to mimic typewriters.

Thus, the first text editors emerged between the 1970s and 1980s, which, along with keyboards like typewriters, allowed information interaction between humans and machines.

Since operating systems were limited to plain text, this form of input was the majority and met the requirements.

The advent of graphical elements, already in the 1990s, required developers to find new ways to input information, not only in text format but also in file formats, images, videos, and audio.

In terms of processing size measured in megabytes, the difference became enormous. While large amounts of text can be stored in very few megabytes, images and videos can easily reach gigabytes.

The popularization of the internet has made file uploading even more necessary. The Merriam-Webster dictionary defines uploading as the transfer of data or files from one digital device to the memory of another device, especially via a computer network, popularly known as the internet.

File Upload Methods: Then and Now

Unlike downloading, where user interaction occurs from the server to the client side, uploading requires data transfer from the client to the server. Because the server structure is generally more complex, file uploading tends to cause more problems.

There are several methods for uploading. The historically best-known and simplest is the File Transfer Protocol (FTP). As Gavin Wright explains in an article on TechTarget, it uses a program to log on to a server and transfer the files.

Hypertext Transfer Protocol (HTTP) uses the same protocol used by websites to send data to servers. In a peer-to-peer (P2P) style, the client and file recipient communicate through a hosting center.

Even with different methods, the list of complaints about file upload plugins is immense.

On the other hand, there are professional tools that can help developers implement a file upload plugin that presents an unpleasant experience.

In general, these are paid services that require a maintenance subscription. There are options in various pricing formats. It is recommended to scale the size and amount of data that the system will support.

The best file upload systems allow integration with development systems like WordPress. Some of them let you easily handle files by doing transformations and size conversions.

Common Pain Points in 2025

• Integration Complexity — Many plugins require extensive configuration or conflict with themes and other plugins.
• Compatibility Issues — WordPress updates or PHP version changes can break existing upload features.
• Security Concerns — Insufficient validation can open vulnerabilities.
• Performance Limits — Default server settings (like PHP upload_max_filesize) cause errors with large files.

Expert Insight: According to Mika Epstein, a long-time WordPress plugin team contributor, “Most file upload problems aren’t caused by the plugin itself but by server-level settings that limit upload size or execution time.”

Practical Fixes and Workarounds

• Use Chunked Uploads: Splits large files into manageable parts, reducing timeout errors.
• Choose Actively Maintained Plugins: Look for recent updates and high ratings.
• Consider Direct-to-Cloud Uploads: Services like Filestack’s WordPress integration handle transformations and storage externally.

Choosing the Right Solution

Ask yourself:

• Do you need a quick setup or deep customization?
• Will your site handle large media files?
• Is your hosting environment flexible?

Daniel Santos is a computer engineer and technology journalist who has covered front-end issues for specialized publications for over 5 years.

Transparency & Methodology

This article draws from first-hand developer complaints on Reddit, Medium, and StackOverflow, as well as expert commentary from recognized WordPress contributors. No affiliate links are included. All product mentions are for informational purposes only.