diff --git a/include/modules/hyprland/workspaces.hpp b/include/modules/hyprland/workspaces.hpp
index d010cb08..528bf933 100644
--- a/include/modules/hyprland/workspaces.hpp
+++ b/include/modules/hyprland/workspaces.hpp
@@ -2,6 +2,7 @@
 
 #include <gtkmm/button.h>
 #include <gtkmm/label.h>
+#include <json/value.h>
 
 #include <cstddef>
 #include <cstdint>
@@ -17,7 +18,6 @@
 #include "util/enum.hpp"
 
 using WindowAddress = std::string;
-using mywindowtype = std::string;
 namespace waybar::modules::hyprland {
 
 class Workspaces;
@@ -47,9 +47,7 @@ class Workspace {
   void set_windows(uint value) { windows_ = value; };
   void set_name(std::string value) { name_ = value; };
   bool contains_window(WindowAddress addr) { return window_map_.contains(addr); }
-  void insert_window(WindowAddress addr, mywindowtype window_repr) {
-    window_map_.emplace(addr, window_repr);
-  };
+  void insert_window(WindowAddress addr, std::string window_repr);
   void remove_window(WindowAddress addr) { window_map_.erase(addr); }
   void initialize_window_map(const Json::Value& clients_data);
 
@@ -77,7 +75,7 @@ class Workspace {
   bool is_urgent_ = false;
   bool is_visible_ = false;
 
-  std::map<WindowAddress, mywindowtype> window_map_;
+  std::map<WindowAddress, std::string> window_map_;
 
   Gtk::Button button_;
   Gtk::Box content_;
@@ -97,6 +95,9 @@ class Workspaces : public AModule, public EventHandler {
 
   auto get_bar_output() const -> std::string { return bar_.output->name; }
 
+  std::string get_rewrite(std::string window_class);
+  std::string& get_window_separator() { return format_window_separator_; }
+
  private:
   void onEvent(const std::string&) override;
   void update_window_count();
@@ -132,7 +133,8 @@ class Workspaces : public AModule, public EventHandler {
 
   std::string format_;
   std::map<std::string, std::string> icons_map_;
-  std::map<std::string, std::string> window_rewrite_rules_;
+  Json::Value window_rewrite_rules_;
+  std::map<std::string, std::string> regex_cache_;
   std::string format_window_separator_;
   bool with_icon_;
   uint64_t monitor_id_;
diff --git a/src/modules/hyprland/workspaces.cpp b/src/modules/hyprland/workspaces.cpp
index 4176851a..43cd7774 100644
--- a/src/modules/hyprland/workspaces.cpp
+++ b/src/modules/hyprland/workspaces.cpp
@@ -9,6 +9,8 @@
 #include <memory>
 #include <string>
 
+#include "util/rewrite_string.hpp"
+
 namespace waybar::modules::hyprland {
 
 Workspaces::Workspaces(const std::string &id, const Bar &bar, const Json::Value &config)
@@ -74,13 +76,7 @@ auto Workspaces::parse_config(const Json::Value &config) -> void {
   format_window_separator_ =
       format_window_separator.isString() ? format_window_separator.asString() : " ";
 
-  Json::Value window_rewrite_map = config["window-rewrite-map"];
-
-  if (window_rewrite_map.isObject()) {
-    for (std::string &name : window_rewrite_map.getMemberNames()) {
-      window_rewrite_rules_.emplace(name, window_rewrite_map[name].asString());
-    }
-  }
+  window_rewrite_rules_ = config["window-rewrite"];
 }
 
 auto Workspaces::register_ipc() -> void {
@@ -234,26 +230,19 @@ void Workspaces::on_window_opened(std::string payload) {
 
   std::string window_title = payload.substr(next_comma_idx + 1, payload.length() - next_comma_idx);
 
-  fmt::println("> Inserting window [{}] [{}] [{}] [{}]", window_address, workspace_name,
-               window_class, window_title);
-
   for (auto &workspace : workspaces_) {
     if (workspace->on_window_opened(window_address, workspace_name, window_class, window_title)) {
       break;
     }
   }
-
-  fmt::println("<");
 }
 
 void Workspaces::on_window_closed(std::string addr) {
-  fmt::println("> Removing window [{}]", addr);
   for (auto &workspace : workspaces_) {
     if (workspace->on_window_closed(addr)) {
       break;
     }
   }
-  fmt::println("<");
 }
 
 void Workspaces::on_window_moved(std::string payload) {
@@ -268,8 +257,6 @@ void Workspaces::on_window_moved(std::string payload) {
 
   const Json::Value clients_json = gIPC->getSocket1JsonReply("clients");
 
-  fmt::println(">> Moving window [{}] [{}]", window_address, workspace_name);
-
   for (auto &workspace : workspaces_) {
     if (workspace->on_window_moved(window_address, workspace_name, clients_json)) {
       changes++;
@@ -278,8 +265,6 @@ void Workspaces::on_window_moved(std::string payload) {
       }
     }
   }
-
-  fmt::println("<<");
 }
 
 void Workspaces::update_window_count() {
@@ -317,10 +302,13 @@ void Workspace::initialize_window_map(const Json::Value &clients_data) {
   }
 }
 
+void Workspace::insert_window(WindowAddress addr, std::string window_class) {
+  window_map_.emplace(addr, workspace_manager_.get_rewrite(window_class));
+};
+
 bool Workspace::on_window_opened(WindowAddress &addr, std::string &workspace_name,
                                  const Json::Value &clients_data) {
   if (workspace_name == name()) {
-    fmt::println("\tInserting on workspace {}", id());
     for (auto client : clients_data) {
       auto client_address = client["address"].asString().substr(2, addr.length());
       if (client_address == addr) {
@@ -329,7 +317,6 @@ bool Workspace::on_window_opened(WindowAddress &addr, std::string &workspace_nam
         return true;
       }
     }
-    fmt::println("\tERROR on workspace {}", id());
     return false;
   } else {
     return false;
@@ -339,7 +326,6 @@ bool Workspace::on_window_opened(WindowAddress &addr, std::string &workspace_nam
 bool Workspace::on_window_opened(WindowAddress &addr, std::string &workspace_name,
                                  std::string &window_class, std::string &window_title) {
   if (workspace_name == name()) {
-    fmt::println("\tInserting on workspace {}", id());
     insert_window(addr, window_class);
     return true;
   } else {
@@ -349,7 +335,6 @@ bool Workspace::on_window_opened(WindowAddress &addr, std::string &workspace_nam
 
 bool Workspace::on_window_closed(WindowAddress &addr) {
   if (window_map_.contains(addr)) {
-    fmt::println("\tRemoving on workspace {}", id());
     remove_window(addr);
     return true;
   } else {
@@ -581,15 +566,22 @@ void Workspace::update(const std::string &format, const std::string &icon) {
   add_or_remove_class(style_context, is_urgent(), "urgent");
   add_or_remove_class(style_context, is_visible(), "visible");
 
-  std::string first_letters;
+  std::string windows;
+  auto window_separator = workspace_manager_.get_window_separator();
+
+  bool is_not_first = false;
 
   for (auto &[_pid, window_repr] : window_map_) {
-    first_letters.append(window_repr.substr(0, 1));
+    if (is_not_first) {
+      windows.append(window_separator);
+    }
+    is_not_first = true;
+    windows.append(window_repr);
   }
 
   label_.set_markup(fmt::format(fmt::runtime(format), fmt::arg("id", id()),
                                 fmt::arg("name", name()), fmt::arg("icon", icon),
-                                fmt::arg("windows", first_letters)));
+                                fmt::arg("windows", windows)));
 }
 
 void Workspaces::sort_workspaces() {
@@ -748,4 +740,17 @@ void Workspaces::set_urgent_workspace(std::string windowaddress) {
   }
 }
 
+std::string Workspaces::get_rewrite(std::string window_class) {
+  if (regex_cache_.contains(window_class)) {
+    return regex_cache_[window_class];
+  }
+
+  std::string window_class_rewrite =
+      waybar::util::rewriteString(window_class, window_rewrite_rules_);
+
+  regex_cache_.emplace(window_class, window_class_rewrite);
+
+  return window_class_rewrite;
+}
+
 }  // namespace waybar::modules::hyprland
diff --git a/src/util/rewrite_string.cpp b/src/util/rewrite_string.cpp
index 40c71e99..ec3e1673 100644
--- a/src/util/rewrite_string.cpp
+++ b/src/util/rewrite_string.cpp
@@ -1,5 +1,6 @@
 #include "util/rewrite_string.hpp"
 
+#include <fmt/core.h>
 #include <spdlog/spdlog.h>
 
 #include <regex>
@@ -17,7 +18,7 @@ std::string rewriteString(const std::string& value, const Json::Value& rules) {
       try {
         // malformated regexes will cause an exception.
         // in this case, log error and try the next rule.
-        const std::regex rule{it.key().asString()};
+        const std::regex rule{it.key().asString(), std::regex_constants::icase};
         if (std::regex_match(value, rule)) {
           res = std::regex_replace(res, rule, it->asString());
         }