diff --git a/main/source/window/window.cpp b/main/source/window/window.cpp
index 3ed231b2d..06d62bdd7 100644
--- a/main/source/window/window.cpp
+++ b/main/source/window/window.cpp
@@ -576,9 +576,10 @@ namespace hex {
                     }
                 }
 
-                if (!open || !popupDisplaying) {
+                if (!open && !popupDisplaying) {
                     sizeSet = false;
                     popupDisplaying = false;
+                    popupSize = ImVec2(0, 0);
                     popups.pop_back();
                 }
             }
diff --git a/plugins/builtin/include/content/popups/popup_docs_question.hpp b/plugins/builtin/include/content/popups/popup_docs_question.hpp
new file mode 100644
index 000000000..194e915e9
--- /dev/null
+++ b/plugins/builtin/include/content/popups/popup_docs_question.hpp
@@ -0,0 +1,128 @@
+#include <hex/ui/popup.hpp>
+
+#include <hex/ui/imgui_imhex_extensions.h>
+
+#include <hex/api/localization.hpp>
+#include <hex/helpers/http_requests.hpp>
+
+#include <functional>
+#include <string>
+
+namespace hex::plugin::builtin {
+
+    class PopupDocsQuestion : public Popup<PopupDocsQuestion> {
+    public:
+        PopupDocsQuestion()
+            : hex::Popup<PopupDocsQuestion>("hex.builtin.popup.docs_question.title", true, true) { }
+
+        enum class TextBlockType {
+            Text,
+            Code
+        };
+
+        void drawContent() override {
+            ImGui::PushItemWidth(600_scaled);
+            ImGui::BeginDisabled(this->m_requestTask.isRunning());
+            if (ImGui::InputText("##input", this->m_inputBuffer, ImGuiInputTextFlags_EnterReturnsTrue)) {
+                this->executeQuery();
+            }
+            ImGui::EndDisabled();
+            ImGui::PopItemWidth();
+
+            if (ImGui::BeginChild("##answer", scaled(ImVec2(600, 350)), true, ImGuiWindowFlags_AlwaysVerticalScrollbar)) {
+                if (!this->m_requestTask.isRunning()) {
+                    if (this->m_answer.empty()) {
+                        if (this->m_noAnswer)
+                            ImGui::TextFormattedCentered("{}", "hex.builtin.popup.docs_question.no_answer"_lang);
+                        else
+                            ImGui::TextFormattedCentered("{}", "hex.builtin.popup.docs_question.prompt"_lang);
+                    } else {
+                        for (auto &[type, text] : this->m_answer) {
+                            switch (type) {
+                                case TextBlockType::Text:
+                                    ImGui::TextFormattedWrapped("{}", text);
+                                    break;
+                                case TextBlockType::Code:
+                                    ImGui::PushStyleColor(ImGuiCol_ChildBg, ImGui::GetStyle().Colors[ImGuiCol_WindowBg]);
+                                    auto textWidth = 400_scaled - ImGui::GetStyle().FramePadding.x * 4 - ImGui::GetStyle().ScrollbarSize;
+                                    auto textHeight = ImGui::CalcTextSize(text.c_str(), nullptr, false, textWidth).y + ImGui::GetStyle().FramePadding.y * 6;
+                                    if (ImGui::BeginChild("##code", ImVec2(textWidth, textHeight), true)) {
+                                        ImGui::TextFormattedWrapped("{}", text);
+                                        ImGui::EndChild();
+                                    }
+                                    ImGui::PopStyleColor();
+
+                                    break;
+                            }
+                        }
+                    }
+                } else {
+                    ImGui::TextFormattedCentered("{}", "hex.builtin.popup.docs_question.thinking"_lang);
+                }
+            }
+            ImGui::EndChild();
+        }
+
+        [[nodiscard]] ImGuiWindowFlags getFlags() const override {
+            return ImGuiWindowFlags_NoResize | ImGuiWindowFlags_AlwaysAutoResize;
+        }
+
+    private:
+        void executeQuery() {
+            this->m_requestTask = TaskManager::createBackgroundTask("Query Docs", [this, input = this->m_inputBuffer](Task &) {
+                this->m_noAnswer = false;
+                for (auto space : { "xj7sbzGbHH260vbpZOu1", "WZzDdGjxmgMSIE3xly6o" }) {
+                    this->m_answer.clear();
+
+                    auto request = HttpRequest("POST", hex::format("https://api.gitbook.com/v1/spaces/{}/search/ask", space));
+
+                    request.setBody(hex::format(R"({{ "query": "{}" }})", input));
+                    request.addHeader("Content-Type", "application/json");
+
+                    auto response = request.execute().get();
+                    if (!response.isSuccess())
+                        continue;
+
+                    try {
+                        auto json = nlohmann::json::parse(response.getData());
+                        if (!json.contains("answer"))
+                            continue;
+
+                        auto answer = json["answer"]["text"].get<std::string>();
+                        if (answer.empty())
+                            break;
+
+                        auto blocks = wolv::util::splitString(answer, "```");
+                        for (auto &block : blocks) {
+                            if (block.empty())
+                                continue;
+
+                            block = wolv::util::trim(block);
+
+                            if (block.starts_with("rust\n")) {
+                                block = block.substr(5);
+                                this->m_answer.emplace_back(TextBlockType::Code, block);
+                            } else if (block.starts_with("cpp\n")) {
+                                block = block.substr(4);
+                                this->m_answer.emplace_back(TextBlockType::Code, block);
+                            } else {
+                                this->m_answer.emplace_back(TextBlockType::Text, block);
+                            }
+                        }
+                    } catch(...) {
+                        continue;
+                    }
+
+                    this->m_noAnswer = this->m_answer.empty();
+                }
+            });
+        }
+
+    private:
+        std::string m_inputBuffer;
+        std::vector<std::pair<TextBlockType, std::string>> m_answer;
+        TaskHolder m_requestTask;
+        bool m_noAnswer = false;
+    };
+
+}
\ No newline at end of file
diff --git a/plugins/builtin/romfs/lang/en_US.json b/plugins/builtin/romfs/lang/en_US.json
index 27ea52dba..0b72fd7d8 100644
--- a/plugins/builtin/romfs/lang/en_US.json
+++ b/plugins/builtin/romfs/lang/en_US.json
@@ -179,6 +179,7 @@
         "hex.builtin.menu.file.quit": "Quit ImHex",
         "hex.builtin.menu.file.reload_provider": "Reload Provider",
         "hex.builtin.menu.help": "Help",
+        "hex.builtin.menu.help.ask_for_help": "Ask Documentation...",
         "hex.builtin.menu.layout": "Layout",
         "hex.builtin.menu.view": "View",
         "hex.builtin.menu.view.demo": "Show ImGui Demo",
@@ -361,6 +362,10 @@
         "hex.builtin.pl_visualizer.3d.scale": "Scale",
         "hex.builtin.popup.close_provider.desc": "There are unsaved changes made to this Provider\nthat haven't been saved to a Project yet.\n\nAre you sure you want to close it?",
         "hex.builtin.popup.close_provider.title": "Close Provider?",
+        "hex.builtin.popup.docs_question.title": "Documentation query",
+        "hex.builtin.popup.docs_question.no_answer": "The documentation didn't have an answer for this question",
+        "hex.builtin.popup.docs_question.prompt": "Ask the documentation AI for help!",
+        "hex.builtin.popup.docs_question.thinking": "Thinking...",
         "hex.builtin.popup.error.create": "Failed to create new file!",
         "hex.builtin.popup.error.file_dialog.common": "An error occurred while opening the file browser: {}",
         "hex.builtin.popup.error.file_dialog.portal": "There was an error while opening the file browser: {}.\nThis might be caused by your system not having a xdg-desktop-portal backend installed correctly.\n\nOn KDE, it's xdg-desktop-portal-kde.\nOn Gnome it's xdg-desktop-portal-gnome.\nOn wlroots it's xdg-desktop-portal-wlr.\nOtherwise, you can try to use xdg-desktop-portal-gtk.\n\nReboot your system after installing it.\n\nIf the file browser still doesn't work after this, submit an issue at https://github.com/WerWolv/ImHex/issues\n\nIn the meantime files can still be opened by dragging them onto the ImHex window!",
diff --git a/plugins/builtin/source/content/main_menu_items.cpp b/plugins/builtin/source/content/main_menu_items.cpp
index 5b997a410..e7c086bcd 100644
--- a/plugins/builtin/source/content/main_menu_items.cpp
+++ b/plugins/builtin/source/content/main_menu_items.cpp
@@ -12,6 +12,7 @@
 
 #include "content/global_actions.hpp"
 #include <content/popups/popup_notification.hpp>
+#include <content/popups/popup_docs_question.hpp>
 
 #include <wolv/io/file.hpp>
 
@@ -453,6 +454,10 @@ namespace hex::plugin::builtin {
 
     static void createHelpMenu() {
         ContentRegistry::Interface::registerMainMenuItem("hex.builtin.menu.help", 5000);
+
+        ContentRegistry::Interface::addMenuItem({ "hex.builtin.menu.help", "hex.builtin.menu.help.ask_for_help" }, 5000, CTRLCMD + SHIFT + Keys::D, [] {
+            PopupDocsQuestion::open();
+        });
     }
 
     void registerMainMenuEntries() {