A practical guide to Zendesk online chat for 2025

Let’s be honest, when a customer has a question, they want an answer right now. Zendesk is a huge name in customer service, and their online chat is a go-to for many businesses trying to offer that real-time support. But getting the hang of their system, especially with the big switch from their old "Chat" to the newer "Messaging" platform, can feel like a puzzle. A lot of teams get stuck dealing with technical roadblocks, especially when they want to plug in custom AI or just make the chat widget look and feel like their own brand without a developer on standby.

This guide is here to walk you through what Zendesk online chat is all about. We’ll cover its main features, untangle the pricing plans, and talk about the common headaches users run into. We’ll also show you a much simpler way to beef up your Zendesk setup with some seriously smart AI, giving you more power without the complicated setup.

What is Zendesk online chat?

When you hear people talk about Zendesk online chat these days, they’re almost always talking about Zendesk Messaging. This is their modern, AI-friendly platform for handling customer conversations. It’s built to work smoothly across your website, mobile app, and even social media channels like WhatsApp or Facebook Messenger.

It’s good to know this isn’t the same as Zendesk’s older "Chat" product (which you might remember as Zopim). That one is now considered legacy. While plenty of businesses are still using it, Zendesk is nudging everyone to migrate over to Messaging. The main difference? Messaging is designed for ongoing conversations that can be picked up anytime, anywhere, and it has much deeper AI integrations. The old Chat was more about one-off, live conversations that ended when the window closed.

The whole idea behind Zendesk Messaging is to keep the entire conversation with a customer in one place, no matter how they contact you, and use AI to handle the easy stuff. The catch, as we’ll get into, is that setting up a truly customized and smart system inside Zendesk can be a real project for your technical team.

Key features of Zendesk online chat

Zendesk Messaging is packed with features to help you manage customer chats. Let’s break down the most important ones.

AI agents and automation

Zendesk puts a lot of focus on its built-in AI. You can create AI agents, which are basically chatbots, to field common questions, find answers in your help center, and send tricky issues to the right human agent. They’re great for handling the repetitive questions that pop up all day, freeing up your team to focus on the tougher problems.

The main limitation here, though, is that the Zendesk AI mostly pulls from your curated knowledge base. If the answer isn’t written down in one of your help articles, the bot is usually stumped. This means you’re constantly having to write and update articles, and it doesn’t tap into the most valuable source of information you have: all your past, successfully resolved tickets.

The unified agent workspace

One of the best things about Zendesk is its unified agent workspace. It pulls in conversations from email, chat, social media, and phone calls all into one neat view. This gives your agents the full backstory on a customer’s issues, which helps them give better, more personal support. Agents can juggle a few conversations at once without having to click between a bunch of different browser tabs.

A screenshot of the Zendesk Agent Workspace, illustrating the unified view for managing customer conversations in Zendesk online chat.

Omnichannel support and routing

Zendesk lets you set up your support system once and then roll it out everywhere. The same automated workflows and AI agents you build for your website can also work in your mobile app or on social media. It also has some clever routing features that can send conversations to agents based on their expertise, availability, or what the customer is asking about. It’s a powerful feature, but setting up detailed routing rules can get complicated and often pushes you into their more expensive plans.

An image of Zendesk's omnichannel ticket view, which is a key feature of the Zendesk online chat experience.

The challenges of setting up and customizing Zendesk online chat

While Zendesk is a solid platform, bending it to your will can be tough, especially if you don’t have developers ready to jump in and help.

Migrating from legacy chat to messaging

For businesses that have been with Zendesk for a while, the move from the old "Chat" to the new "Messaging" platform is a pretty big deal. The technology behind them is totally different, so you have to rebuild your workflows from the ground up. It’s a classic example of being in a "walled garden"; you have to follow their roadmap, even if it means a lot of extra work for your team.

Customizing the chat experience: Why you might need a developer

Most companies want their chat widget to feel like a seamless part of their website, not a clunky add-on. But as you can see in discussions on forums like Reddit, it’s a common struggle to get Zendesk to handle the chat logic while you control how it looks and feels.

Reddit

To do this, you have to dig deep into their Sunshine Conversations API, which is not a task for the faint of heart. If you want to do something as simple as putting a layer of AI in front of Zendesk without using their pre-built widget, you’re looking at a serious engineering project.

Integrating third-party AI and external knowledge

Zendesk’s AI is a decent starting point, but what if you want something smarter? Something that learns from all your company knowledge, not just the help center? Trying to connect a different AI tool or pull in knowledge from places like Confluence, Google Docs, or your old support tickets is not a simple, out-of-the-box option. This is where you can start to feel boxed in. You’re either stuck with the limits of their native AI or looking at yet another complex API project.

This is a huge point of frustration for support teams. They want the power of modern AI but don’t want to leave the helpdesk they already know. Luckily, some tools are built to fix this exact problem. For example, eesel AI integrates directly with your Zendesk account in just a few clicks. Instead of a months-long custom integration, you can connect eesel AI to Zendesk and all your other knowledge sources. You get a genuinely smart AI agent that’s ready to go in minutes, not months.

A screenshot showing the eesel AI agent integrated within the Zendesk online chat interface.

A complete breakdown of Zendesk online chat pricing

Zendesk’s pricing is split into different tiers, and it can be a bit confusing to figure out. Key features, especially advanced AI, are often locked away in the more expensive plans. The plans are all billed per agent, per month, so it’s important to know what you’re getting into.

Here’s a quick look at the Zendesk Suite plans, which all include their online chat.

Data sourced from Zendesk’s pricing page in 2024. ARs = Automated Resolutions.

It’s also worth noting that their "Advanced AI agents" and "Copilot" features are sold as separate add-ons, which can really drive up the total cost. With all the different tiers and add-ons, budgeting can get tricky.

The simpler way to add powerful AI to your Zendesk online chat

If the cost and complexity of Zendesk’s native AI are making your head spin, you’re not the only one. Many teams need a faster, more powerful, and more affordable way to automate their support. This is where a tool like eesel AI comes into the picture.

Instead of making you switch platforms or start a huge development project, eesel AI is designed to slide right into your existing setup and make it better. Here’s how it offers a different path:

• Get set up in minutes, not months: eesel AI is completely self-serve. You can connect your Zendesk account with a single click, add all your knowledge sources (like past tickets, Confluence, and Google Docs), and launch your AI agent without ever having to talk to a salesperson.

This workflow demonstrates the quick, self-serve implementation of eesel's AI for Zendesk online chat.

• Bring all your knowledge together: Don’t fence your AI into just a help center. eesel AI learns from your team’s entire brain, including thousands of past tickets and internal documents. This helps it give answers that are accurate, relevant, and sound like they’re coming from you.

An infographic showing how eesel AI integrates various knowledge sources to enhance Zendesk online chat capabilities.

• Test without the risk: Nervous about letting an AI talk to your customers? eesel AI has a simulation mode that lets you test it on thousands of your past tickets. You can see exactly how it would have replied, get solid predictions on how many tickets it will solve, and tweak its behavior before it ever goes live.

A screenshot of the eesel AI simulation mode, a key feature for testing AI responses in your Zendesk online chat environment.

• Clear, predictable pricing: Say goodbye to being charged per resolution and getting hit with surprise add-on fees. eesel AI has straightforward pricing based on usage, so there are no shocks. It’s easy to budget for and scale up without worrying about costs getting out of control.

By plugging into the tools you already use, eesel AI gives you all the perks of a modern AI support system without the pain of ditching and replacing your current helpdesk.

Get more from your Zendesk online chat investment

Zendesk offers a solid platform for Zendesk online chat, but getting it to do everything you want often means paying for higher-tier plans, bringing in developers, and a lot of ongoing admin work. Its native AI is a good first step, but it’s only as smart as the articles you feed it, and making the chat experience your own can be a real technical challenge.

For teams that want a faster, smarter, and more adaptable way to automate support, adding a specialized AI layer on top of Zendesk is often the best move. You keep the helpdesk your team is comfortable with, but you also get a more intelligent, fully connected AI that learns from all your data and gives you total control.

If you’re ready to see what your Zendesk setup can really do, take a look at how eesel AI can transform your customer support.