diff --git a/client/src/components/DatasetInformation/DatasetError.vue b/client/src/components/DatasetInformation/DatasetError.vue
index 001bb403e0ac..75ef23f86c5e 100644
--- a/client/src/components/DatasetInformation/DatasetError.vue
+++ b/client/src/components/DatasetInformation/DatasetError.vue
@@ -53,6 +53,10 @@
                             </a>
                         </b>
                     </p>
+                    <h4 class="mb-3 h-md">What might have happened?</h4>
+                    <b-card>
+                        <GalaxyWizard view="error" :query="jobDetails.tool_stderr" context="tool_error" />
+                    </b-card>
                     <h4 class="mb-3 h-md">Issue Report</h4>
                     <b-alert
                         v-for="(resultMessage, index) in resultMessages"
@@ -89,6 +93,7 @@
 <script>
 import DatasetErrorDetails from "./DatasetErrorDetails";
 import FormElement from "components/Form/FormElement";
+import GalaxyWizard from "components/GalaxyWizard";
 import { DatasetProvider } from "components/providers";
 import { JobDetailsProvider, JobProblemProvider } from "components/providers/JobProvider";
 import { FontAwesomeIcon } from "@fortawesome/vue-fontawesome";
@@ -105,6 +110,7 @@ export default {
         DatasetErrorDetails,
         FontAwesomeIcon,
         FormElement,
+        GalaxyWizard,
         JobDetailsProvider,
         JobProblemProvider,
         CurrentUser,
diff --git a/client/src/components/GalaxyWizard.vue b/client/src/components/GalaxyWizard.vue
new file mode 100644
index 000000000000..9206db372506
--- /dev/null
+++ b/client/src/components/GalaxyWizard.vue
@@ -0,0 +1,87 @@
+<script setup lang="ts">
+import axios from "axios";
+import { ref } from "vue";
+import Heading from "./Common/Heading.vue";
+import LoadingSpan from "./LoadingSpan.vue";
+
+const props = defineProps({
+    view: {
+        type: String,
+        default: "wizard",
+    },
+    query: {
+        type: String,
+        default: "",
+    },
+    context: {
+        type: String,
+        default: "",
+    },
+});
+
+const query = ref(props.query);
+const queryResponse = ref("");
+
+const busy = ref(false);
+
+// on submit, query the server and put response in display box
+function submitQuery() {
+    busy.value = true;
+    queryResponse.value = "";
+    const context = props.context || "username";
+    axios
+        .post("/api/chat", {
+            query: query.value,
+            context: context,
+        })
+        .then(function (response) {
+            console.log(response);
+            queryResponse.value = response.data;
+        })
+        .catch(function (error) {
+            console.error(error);
+        })
+        .finally(() => {
+            busy.value = false;
+        });
+}
+</script>
+<template>
+    <div>
+        <!-- input text, full width top of page -->
+        <Heading v-if="props.view == 'wizard'" inline h2>Ask the wizard</Heading>
+        <div :class="props.view == 'wizard' && 'mt-2'">
+            <b-input
+                v-if="props.query == ''"
+                id="wizardinput"
+                v-model="query"
+                style="width: 100%"
+                placeholder="What's the difference in fasta and fastq files?"
+                @keyup.enter="submitQuery" />
+            <b-button
+                v-else-if="!queryResponse"
+                variant="info"
+                :disabled="busy"
+                @click="submitQuery">
+                <span v-if="!busy">
+                    Let our Help Wizard Figure it out!
+                </span>
+                <LoadingSpan v-else message="Thinking..." />
+            </b-button>
+        </div>
+        <!-- spinner when busy -->
+        <div :class="props.view == 'wizard' && 'mt-4'">
+            <div v-if="busy">
+                <b-skeleton animation="wave" width="85%"></b-skeleton>
+                <b-skeleton animation="wave" width="55%"></b-skeleton>
+                <b-skeleton animation="wave" width="70%"></b-skeleton>
+            </div>
+            <div v-else class="chatResponse">{{ queryResponse }}</div>
+        </div>
+    </div>
+</template>
+<style lang="scss" scoped>
+.chatResponse {
+    white-space: pre-wrap;
+}
+</style>
diff --git a/client/src/entry/analysis/menu.js b/client/src/entry/analysis/menu.js
index ddbfcb3f0e65..fdb84c2d8fc7 100644
--- a/client/src/entry/analysis/menu.js
+++ b/client/src/entry/analysis/menu.js
@@ -113,6 +113,10 @@ export function fetchMenu(options = {}) {
                 target: "_blank",
                 hidden: !options.helpsite_url,
             },
+            {
+                title: _l("Help Wizard"),
+                url: "/wizard",
+            },
             {
                 title: _l("Support"),
                 url: options.support_url,
diff --git a/client/src/entry/analysis/router.js b/client/src/entry/analysis/router.js
index 35f234452422..74317399691e 100644
--- a/client/src/entry/analysis/router.js
+++ b/client/src/entry/analysis/router.js
@@ -66,6 +66,8 @@ import { ExternalIdentities } from "components/User/ExternalIdentities";
 import { HistoryExport } from "components/HistoryExport/index";
 import HistoryExportTasks from "components/History/Export/HistoryExport";
 
+import GalaxyWizard from "components/GalaxyWizard";
+
 Vue.use(VueRouter);
 
 // patches $router.push() to trigger an event and hide duplication warnings
@@ -318,6 +320,10 @@ export function getRouter(Galaxy) {
                         path: "tours",
                         component: TourList,
                     },
+                    {
+                        path: "wizard",
+                        component: GalaxyWizard,
+                    },
                     {
                         path: "tours/:tourId",
                         component: TourRunner,
diff --git a/client/src/schema/schema.ts b/client/src/schema/schema.ts
index c8ac40bba525..4b6046685e29 100644
--- a/client/src/schema/schema.ts
+++ b/client/src/schema/schema.ts
@@ -8,6 +8,13 @@ export interface paths {
         /** Returns returns an API key for authenticated user based on BaseAuth headers. */
         get: operations["get_api_key_api_authenticate_baseauth_get"];
     };
+    "/api/chat": {
+        /**
+         * Query
+         * @description We're off to ask the wizard
+         */
+        post: operations["query_api_chat_post"];
+    };
     "/api/configuration": {
         /**
          * Return an object containing exposable configuration settings
@@ -1600,6 +1607,23 @@ export interface components {
              */
             type: "change_dbkey";
         };
+        /**
+         * ChatPayload
+         * @description Base model definition with common configuration used by all derived models.
+         */
+        ChatPayload: {
+            /**
+             * Message
+             * @description The message to be sent to the chat.
+             */
+            query: string;
+            /**
+             * Context
+             * @description The context identifier to be used by the chat.
+             * @enum {string}
+             */
+            context?: "username" | "tool_error";
+        };
         /**
          * CheckForUpdatesResponse
          * @description Base model definition with common configuration used by all derived models.
@@ -7630,6 +7654,31 @@ export interface operations {
             };
         };
     };
+    query_api_chat_post: {
+        /**
+         * Query
+         * @description We're off to ask the wizard
+         */
+        requestBody: {
+            content: {
+                "application/json": components["schemas"]["ChatPayload"];
+            };
+        };
+        responses: {
+            /** @description Successful Response */
+            200: {
+                content: {
+                    "application/json": string;
+                };
+            };
+            /** @description Validation Error */
+            422: {
+                content: {
+                    "application/json": components["schemas"]["HTTPValidationError"];
+                };
+            };
+        };
+    };
     index_api_configuration_get: {
         /**
          * Return an object containing exposable configuration settings
diff --git a/doc/source/admin/galaxy_options.rst b/doc/source/admin/galaxy_options.rst
index 3d54bea52166..2df35e9f8f5a 100644
--- a/doc/source/admin/galaxy_options.rst
+++ b/doc/source/admin/galaxy_options.rst
@@ -4944,6 +4944,17 @@
 :Type: int
 
 
+~~~~~~~~~~~~~~~~~~
+``openai_api_key``
+~~~~~~~~~~~~~~~~~~
+
+:Description:
+    API key for OpenAI (https://openai.com/) to enable the wizard (or
+    more?)
+:Default: ``None``
+:Type: str
+
+
 ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~
 ``enable_tool_recommendations``
 ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~
diff --git a/lib/galaxy/config/sample/galaxy.yml.sample b/lib/galaxy/config/sample/galaxy.yml.sample
index fdb8f94fbc7e..59a4d9db2d39 100644
--- a/lib/galaxy/config/sample/galaxy.yml.sample
+++ b/lib/galaxy/config/sample/galaxy.yml.sample
@@ -2648,6 +2648,10 @@ galaxy:
   # as threshold (above threshold: regular select fields will be used)
   #select_type_workflow_threshold: -1
 
+  # API key for OpenAI (https://openai.com/) to enable the wizard (or
+  # more?)
+  #openai_api_key: null
+
   # Allow the display of tool recommendations in workflow editor and
   # after tool execution. If it is enabled and set to true, please
   # enable 'tool_recommendation_model_path' as well
diff --git a/lib/galaxy/config/schemas/config_schema.yml b/lib/galaxy/config/schemas/config_schema.yml
index 3e6b1881c627..027d8008ae1c 100644
--- a/lib/galaxy/config/schemas/config_schema.yml
+++ b/lib/galaxy/config/schemas/config_schema.yml
@@ -3609,6 +3609,12 @@ mapping:
           use -1 (default) in order to always use the regular select fields,
           use any other positive number as threshold (above threshold: regular select fields will be used)
 
+      openai_api_key:
+        type: str
+        required: false
+        desc: |
+          API key for OpenAI (https://openai.com/) to enable the wizard (or more?)
+
       enable_tool_recommendations:
         type: bool
         default: false
diff --git a/lib/galaxy/dependencies/__init__.py b/lib/galaxy/dependencies/__init__.py
index 79526e490304..42d2ea49a339 100644
--- a/lib/galaxy/dependencies/__init__.py
+++ b/lib/galaxy/dependencies/__init__.py
@@ -280,6 +280,9 @@ def check_influxdb(self):
     def check_tensorflow(self):
         return asbool(self.config["enable_tool_recommendations"])
 
+    def check_openai(self):
+        return self.config.get("openai_api_key", None) is not None
+
     def check_weasyprint(self):
         # See notes in ./conditional-requirements.txt for more information.
         return os.environ.get("GALAXY_DEPENDENCIES_INSTALL_WEASYPRINT") == "1"
diff --git a/lib/galaxy/dependencies/conditional-requirements.txt b/lib/galaxy/dependencies/conditional-requirements.txt
index 8d8a5d9bd55c..28335c054a96 100644
--- a/lib/galaxy/dependencies/conditional-requirements.txt
+++ b/lib/galaxy/dependencies/conditional-requirements.txt
@@ -14,6 +14,7 @@ python-pam
 galaxycloudrunner
 pkce
 total-perspective-vortex<3
+openai
 
 # For file sources plugins
 fs.webdavfs>=0.4.2  # type: webdav
diff --git a/lib/galaxy/schema/schema.py b/lib/galaxy/schema/schema.py
index f70f7680bb3a..ef63c08d7c46 100644
--- a/lib/galaxy/schema/schema.py
+++ b/lib/galaxy/schema/schema.py
@@ -3191,6 +3191,19 @@ class MaterializeDatasetInstanceRequest(MaterializeDatasetInstanceAPIRequest):
     history_id: DecodedDatabaseIdField
 
 
+class ChatPayload(Model):
+    query: str = Field(
+        ...,
+        title="Message",
+        description="The message to be sent to the chat.",
+    )
+    context: Optional[str] = Field(
+        default="",
+        title="Context",
+        description="A context identifier to be used by the chat.",
+    )
+
+
 class CreatePagePayload(PageSummaryBase):
     content_format: PageContentFormat = ContentFormatField
     content: Optional[str] = ContentField
diff --git a/lib/galaxy/webapps/galaxy/api/chat.py b/lib/galaxy/webapps/galaxy/api/chat.py
new file mode 100644
index 000000000000..3f78dfecb9e6
--- /dev/null
+++ b/lib/galaxy/webapps/galaxy/api/chat.py
@@ -0,0 +1,73 @@
+"""
+API Controller providing Chat functionality
+"""
+import logging
+
+try:
+    import openai
+except ImportError:
+    openai = None
+
+from galaxy.config import GalaxyAppConfiguration
+from galaxy.managers.context import ProvidesUserContext
+from galaxy.webapps.galaxy.api import (
+    depends,
+    DependsOnTrans,
+)
+from galaxy.exceptions import ConfigurationError
+from galaxy.schema.schema import ChatPayload
+from . import (
+    depends,
+    Router,
+)
+
+log = logging.getLogger(__name__)
+
+router = Router(tags=["chat"])
+
+PROMPT = """
+You are a highly intelligent question answering agent, expert on the Galaxy analysis platform and in the fields of computer science, bioinformatics, and genomics.
+You will try to answer questions about Galaxy, and if you don't know the answer, you will ask the user to rephrase the question.
+"""
+
+
+@router.cbv
+class ChatAPI:
+    config: GalaxyAppConfiguration = depends(GalaxyAppConfiguration)
+
+    @router.post("/api/chat")
+    def query(self, query: ChatPayload, trans: ProvidesUserContext = DependsOnTrans) -> str:
+        """We're off to ask the wizard"""
+
+        if openai is None or self.config.openai_api_key is None:
+            raise ConfigurationError("OpenAI is not configured for this instance.")
+        else:
+            openai.api_key = self.config.openai_api_key
+
+        messages=[
+            {"role": "system", "content": PROMPT},
+            {"role": "user", "content": query.query},
+        ]
+
+        if query.context == "username":
+            user = trans.user
+            if user is not None:
+                log.debug(f"CHATGPTuser: {user.username}")
+                msg = f"You will address the user as {user.username}"
+            else:
+                msg = f"You will address the user as Anonymous User"
+            messages.append({"role": "system", "content": msg})
+        elif query.context == "tool_error":
+            msg = "The user will provide you a Galaxy tool error, and you will try to debug and explain what happened"
+            messages.append({"role": "system", "content": msg})
+        
+        log.debug(f"CHATGPTmessages: {messages}")
+
+        response = openai.ChatCompletion.create(
+            model="gpt-3.5-turbo",
+            messages=messages,
+            temperature=0,
+        )
+
+        answer = response["choices"][0]["message"]["content"]
+        return answer
diff --git a/lib/galaxy/webapps/galaxy/buildapp.py b/lib/galaxy/webapps/galaxy/buildapp.py
index a9bcaba11314..557022d50de9 100644
--- a/lib/galaxy/webapps/galaxy/buildapp.py
+++ b/lib/galaxy/webapps/galaxy/buildapp.py
@@ -254,6 +254,7 @@ def app_pair(global_conf, load_app_kwds=None, wsgi_preflight=True, **kwargs):
     webapp.add_client_route("/collection/{collection_id}/edit")
     webapp.add_client_route("/jobs/submission/success")
     webapp.add_client_route("/jobs/{job_id}/view")
+    webapp.add_client_route("/wizard")
     webapp.add_client_route("/workflows/list")
     webapp.add_client_route("/workflows/list_published")
     webapp.add_client_route("/workflows/edit")