diff --git a/controlpanel/api/migrations/0050_alter_tool_deprecated_message.py b/controlpanel/api/migrations/0050_alter_tool_deprecated_message.py
new file mode 100644
index 000000000..8a7a2409a
--- /dev/null
+++ b/controlpanel/api/migrations/0050_alter_tool_deprecated_message.py
@@ -0,0 +1,21 @@
+# Generated by Django 5.1.2 on 2024-12-09 15:07
+
+# Third-party
+from django.db import migrations, models
+
+
+class Migration(migrations.Migration):
+
+    dependencies = [
+        ("api", "0049_tool_deprecated_message_tool_is_retired"),
+    ]
+
+    operations = [
+        migrations.AlterField(
+            model_name="tool",
+            name="deprecated_message",
+            field=models.TextField(
+                blank=True, help_text="If no message is provided, a default message will be used."
+            ),
+        ),
+    ]
diff --git a/controlpanel/api/models/tool.py b/controlpanel/api/models/tool.py
index 1303fbc2a..36560403e 100644
--- a/controlpanel/api/models/tool.py
+++ b/controlpanel/api/models/tool.py
@@ -27,6 +27,7 @@ class Tool(TimeStampedModel):
         "rstudio": "rstudio",
         "vscode": "vscode",
     }
+    DEFAULT_DEPRECATED_MESSAGE = "The selected release has been deprecated and will be retired soon. Please update to a more recent version."  # noqa
 
     description = models.TextField(blank=True)
     chart_name = models.CharField(max_length=100, blank=False)
@@ -52,7 +53,9 @@ class Tool(TimeStampedModel):
     )
 
     is_deprecated = models.BooleanField(default=False)
-    deprecated_message = models.TextField(blank=True)
+    deprecated_message = models.TextField(
+        blank=True, help_text="If no message is provided, a default message will be used."
+    )
     is_retired = models.BooleanField(default=False)
 
     class Meta(TimeStampedModel.Meta):
@@ -83,6 +86,16 @@ def image_tag(self):
             "{}.image.tag".format(chart_image_key_name)
         )
 
+    @property
+    def get_deprecated_message(self):
+        if not self.is_deprecated:
+            return ""
+
+        if self.is_retired:
+            return ""
+
+        return self.deprecated_message or self.DEFAULT_DEPRECATED_MESSAGE
+
 
 class ToolDeploymentManager:
     """
diff --git a/controlpanel/frontend/jinja2/release-detail.html b/controlpanel/frontend/jinja2/release-detail.html
index 0cd63c6c0..d74dea699 100644
--- a/controlpanel/frontend/jinja2/release-detail.html
+++ b/controlpanel/frontend/jinja2/release-detail.html
@@ -153,7 +153,7 @@ <h1 class="govuk-heading-xl">{{ page_title }}</h1>
       },
       "classes": "govuk-!-width-two-thirds",
       "hint": {
-        "text": 'A flag to indicate the release is deprecated and will soon become unavailable to deploy'
+        "text": 'Checking this will display a deprecation message to users when they select this release'
       },
       "name": "is_deprecated",
       "items": [
@@ -172,7 +172,7 @@ <h1 class="govuk-heading-xl">{{ page_title }}</h1>
       },
       "classes": "govuk-!-width-two-thirds",
       "hint": {
-        "text": 'A message to display to users if they select this tool'
+        "text": form.deprecated_message.help_text
       },
       "name": "deprecated_message",
       "value": form.deprecated_message.value(),
@@ -188,7 +188,7 @@ <h1 class="govuk-heading-xl">{{ page_title }}</h1>
       },
       "classes": "govuk-!-width-two-thirds",
       "hint": {
-        "text": 'A flag to indicate the release is retired. Users will not be able to deploy this release.'
+        "text": 'Checking this will remove this release from all users dropdown options on the Your Tools page.'
       },
       "name": "is_retired",
       "items": [
diff --git a/controlpanel/frontend/jinja2/tool-list.html b/controlpanel/frontend/jinja2/tool-list.html
index 8648aecf1..3da29b75c 100644
--- a/controlpanel/frontend/jinja2/tool-list.html
+++ b/controlpanel/frontend/jinja2/tool-list.html
@@ -41,16 +41,22 @@ <h2 class="govuk-heading-m">{{ tool_info.name }}</h2>
             {% if deployment and deployment.tool_id > -1 %}
               {% set installed_chart_version = deployment.description %}
               {% set installed_release_version = deployment.tool_id %}
-              <option class="installed" value="{{ deployment.chart_name }}__{{ installed_chart_version }}__{{ deployment.tool_id }}">
-              [{{ deployment.chart_name }} {{ deployment.image_tag }}]  {{ installed_chart_version or "Unknown" }} (installed)
+              <option class="installed" value="{{ deployment.chart_name }}__{{ installed_chart_version }}__{{ deployment.tool_id }}"
+                data-is-deprecated="{{ deployment.is_deprecated }}"
+                data-deprecated-message="{{ deployment.deprecated_message }}">
+                {% if deployment.is_deprecated %}DEPRECATED {% endif %}[{{ deployment.chart_name }} {{ deployment.image_tag }}]  {{ installed_chart_version or "Unknown" }} (installed)
               </option>
             {% else %}
               <option class="not-installed">Not deployed - select a tool from this list and click "Deploy" to start</option>
             {% endif %}
             {% for release_version, release_detail in tool_info["releases"].items(): %}
               {% if release_version != installed_release_version: %}
-                <option value="{{ release_detail.chart_name }}__{{ release_detail.chart_version }}__{{ release_detail.tool_id }}">
-                  [{{ release_detail.chart_name }} {{ release_detail.image_tag }}]  {{ release_detail.description or "Unknown" }}
+                <option
+                value="{{ release_detail.chart_name }}__{{ release_detail.chart_version }}__{{ release_detail.tool_id }}"
+                data-is-deprecated="{{ release_detail.is_deprecated }}"
+                data-deprecated-message="{{ release_detail.deprecated_message }}">
+                  <!-- TODO rather than build this info up manually in the view we could read it from the tool object itself -->
+                  {% if release_detail.is_deprecated %}DEPRECATED {% endif %}[{{ release_detail.chart_name }} {{ release_detail.image_tag }}]  {{ release_detail.description or "Unknown" }}
                 </option>
               {% endif %}
             {% endfor %}
@@ -107,6 +113,8 @@ <h2 class="govuk-heading-m">{{ tool_info.name }}</h2>
   </div>
 </div>
 
+<div id="{{ chart_name }}-deprecation-message" {% if not deployment or deployment.deprecated_message == "" %}class="govuk-visually-hidden"{% endif %}><p class="govuk-body">{{ deployment.deprecated_message }}</p></div>
+
 {% if deployment and deployment.tool_id == -1 %}
 
 <div>
diff --git a/controlpanel/frontend/static/javascripts/modules/tool-status.js b/controlpanel/frontend/static/javascripts/modules/tool-status.js
index 2121c4b35..ddc61b8e9 100644
--- a/controlpanel/frontend/static/javascripts/modules/tool-status.js
+++ b/controlpanel/frontend/static/javascripts/modules/tool-status.js
@@ -156,5 +156,21 @@ moj.Modules.toolStatus = {
     // If "(not installed)" or "(installed)" version selected
     // the "Deploy" button needs to be disabled
     deployButton.disabled = notInstalledSelected || installedSelected;
+
+    this.toggleDeprecationMessage(selected, targetTool);
   },
+
+  toggleDeprecationMessage(selected, targetTool) {
+    const isDeprecated = selected.attributes["data-is-deprecated"].value === "True";
+    const deprecationMessageElement = document.getElementById(targetTool.value + "-deprecation-message");
+    const deprecationMessage = selected.attributes["data-deprecated-message"].value;
+
+    if (isDeprecated) {
+      deprecationMessageElement.firstChild.innerText = deprecationMessage;
+      deprecationMessageElement.classList.remove(this.hidden);
+    } else {
+      deprecationMessageElement.classList.add(this.hidden);
+      deprecationMessageElement.firstChild.innerText = "";
+    }
+  }
 };
diff --git a/controlpanel/frontend/views/tool.py b/controlpanel/frontend/views/tool.py
index 3cd3f118f..a78e416a1 100644
--- a/controlpanel/frontend/views/tool.py
+++ b/controlpanel/frontend/views/tool.py
@@ -71,13 +71,15 @@ def _find_related_tool_record(self, chart_name, chart_version, image_tag):
         """
         tool_set = Tool.objects.filter(
             chart_name=chart_name, version=chart_version, is_restricted=False
-        )
-        for item in tool_set:
-            if item.image_tag == image_tag:
-                return item
-        return tool_set.first()
+        ).exclude(is_retired=True)
+        for tool in tool_set:
+            if tool.image_tag == image_tag:
+                return tool
+        # If we cant find a tool with the same image tag, this must mean that it was retired or
+        # deleted. So return none, and let the calling function handle it
+        return None
 
-    def _add_new_item_to_tool_box(self, user, tool_box, tool, tools_info, charts_info):
+    def _add_new_item_to_tool_box(self, user, tool_box, tool, tools_info):
         if tool_box not in tools_info:
             tools_info[tool_box] = {
                 "name": tool.name,
@@ -85,16 +87,19 @@ def _add_new_item_to_tool_box(self, user, tool_box, tool, tools_info, charts_inf
                 "deployment": None,
                 "releases": {},
             }
-        image_tag = tool.image_tag
-        if not image_tag:
-            image_tag = charts_info.get(tool.version, {}) or "unknown"
+        # TODO We should update model to always store an image tag
+        # image_tag = tool.image_tag
+        # if not image_tag:
+        #     image_tag = charts_info.get(tool.version, {}) or "unknown"
         if tool.id not in tools_info[tool_box]["releases"]:
             tools_info[tool_box]["releases"][tool.id] = {
                 "tool_id": tool.id,
                 "chart_name": tool.chart_name,
                 "description": tool.description,
                 "chart_version": tool.version,
-                "image_tag": image_tag,
+                "image_tag": tool.image_tag,
+                "is_deprecated": tool.is_deprecated,
+                "deprecated_message": tool.get_deprecated_message,
             }
 
     def _get_tool_deployed_image_tag(self, containers):
@@ -103,8 +108,10 @@ def _get_tool_deployed_image_tag(self, containers):
                 return container.image.split(":")[1]
         return None
 
-    def _add_deployed_charts_info(self, tools_info, user, id_token, charts_info):
+    def _add_deployed_charts_info(self, tools_info, user, id_token):
         # Get list of deployed tools
+        # TODO this sets what tool the user currently has deployed. If we were to refactor to store
+        # deployed tools in the database, we could remove a lot of this logic
         deployments = cluster.ToolDeployment.get_deployments(user, id_token)
         for deployment in deployments:
             chart_name, chart_version = deployment.metadata.labels["chart"].rsplit("-", 1)
@@ -119,7 +126,7 @@ def _add_deployed_charts_info(self, tools_info, user, id_token, charts_info):
                     )
                 )
             else:
-                self._add_new_item_to_tool_box(user, tool_box, tool, tools_info, charts_info)
+                self._add_new_item_to_tool_box(user, tool_box, tool, tools_info)
             if tool_box not in tools_info:
                 # up to this stage, if the tool_box is still empty, it means
                 # there is no tool release available in db
@@ -131,21 +138,26 @@ def _add_deployed_charts_info(self, tools_info, user, id_token, charts_info):
                 "image_tag": image_tag,
                 "description": tool.description if tool else "Not available",
                 "status": ToolDeployment(tool, user).get_status(id_token, deployment=deployment),
+                "is_deprecated": tool.is_deprecated if tool else False,
+                "deprecated_message": tool.get_deprecated_message if tool else "",
+                "is_retired": tool is None,
             }
 
-    def _retrieve_detail_tool_info(self, user, tools, charts_info):
+    def _retrieve_detail_tool_info(self, user, tools):
+        # TODO why do we need this? We could change so that all information required about available tools comes from the DB  # noqa: E501
         tools_info = {}
         for tool in tools:
             # Work out which bucket the chart should be in
             tool_box = self._locate_tool_box_by_chart_name(tool.chart_name)
             # No matching tool bucket for the given chart. So ignore.
             if tool_box:
-                self._add_new_item_to_tool_box(user, tool_box, tool, tools_info, charts_info)
+                self._add_new_item_to_tool_box(user, tool_box, tool, tools_info)
         return tools_info
 
     def _get_charts_info(self, tool_list):
         # We may need the default image_tag from helm chart
         # unless we configure it specifically in parameters of tool release
+        # TODO if we make sure that we always have an image_tag for a tool, then building charts_info is redundant and could be removed  # noqa: E501
         charts_info = {}
         chart_entries = None
         for tool in tool_list:
@@ -229,14 +241,14 @@ def get_context_data(self, *args, **kwargs):
         context["managed_airflow_prod_url"] = f"{settings.AWS_SERVICE_URL}/?{args_airflow_prod_url}"
 
         # Arrange tools information
-        charts_info = self._get_charts_info(context["tools"])
-        tools_info = self._retrieve_detail_tool_info(user, context["tools"], charts_info)
+        # charts_info = self._get_charts_info(context["tools"])
+        tools_info = self._retrieve_detail_tool_info(user, context["tools"])
 
         if "vscode" in tools_info:
             url = tools_info["vscode"]["url"]
             tools_info["vscode"]["url"] = f"{url}?folder=/home/analyticalplatform/workspace"
 
-        self._add_deployed_charts_info(tools_info, user, id_token, charts_info)
+        self._add_deployed_charts_info(tools_info, user, id_token)
         context["tools_info"] = tools_info
         return context