diff --git a/app/models/form_configuration.rb b/app/models/form_configuration.rb
index eaf563791ab0..017d191bfcd3 100644
--- a/app/models/form_configuration.rb
+++ b/app/models/form_configuration.rb
@@ -114,6 +114,7 @@ def persist_staged_attribute_groups
     return unless groups
 
     attribute_group_rows.store(groups)
+    WorkPackage.clear_available_custom_fields_cache
     remove_instance_variable(:@stored_attribute_groups) if defined?(@stored_attribute_groups)
   end
 
diff --git a/app/models/work_package.rb b/app/models/work_package.rb
index 39a069a9fb8d..72b940ec2746 100644
--- a/app/models/work_package.rb
+++ b/app/models/work_package.rb
@@ -49,6 +49,7 @@ class WorkPackage < ApplicationRecord
 
   include OpenProject::Journal::AttachmentHelper
 
+  AVAILABLE_CUSTOM_FIELDS_CACHE_PREFIX = "work_package_custom_fields_"
   DONE_RATIO_OPTIONS = %w[field status].freeze
   TOTAL_PERCENT_COMPLETE_MODE_OPTIONS = %w[work_weighted_average simple_average].freeze
 
@@ -505,6 +506,10 @@ def self.available_custom_fields(work_package)
     end
   end
 
+  def self.clear_available_custom_fields_cache
+    RequestStore.store.delete_if { |key, _| key.to_s.start_with?(AVAILABLE_CUSTOM_FIELDS_CACHE_PREFIX) }
+  end
+
   def self.preload_available_custom_fields(work_packages)
     type_variant_ids = type_variant_ids_by_pair(work_packages)
 
@@ -591,7 +596,7 @@ def self.form_configuration_custom_fields_join(variant_ids)
   private_class_method :form_configuration_custom_fields_join
 
   def self.available_custom_field_key(work_package)
-    :"work_package_custom_fields_#{work_package.project_id}_#{work_package.type_id}"
+    :"#{AVAILABLE_CUSTOM_FIELDS_CACHE_PREFIX}#{work_package.project_id}_#{work_package.type_id}"
   end
 
   private_class_method :available_custom_field_key
diff --git a/spec/models/work_package/work_package_custom_fields_spec.rb b/spec/models/work_package/work_package_custom_fields_spec.rb
index 83be8c80c2a4..18a296a9d08f 100644
--- a/spec/models/work_package/work_package_custom_fields_spec.rb
+++ b/spec/models/work_package/work_package_custom_fields_spec.rb
@@ -457,5 +457,14 @@ def self.change_custom_field_value(work_package, value, save: true)
     it "offers a field the applied variant's form configuration shows" do
       expect(work_package.available_custom_fields).to include(field)
     end
+
+    it "picks up a field the form configuration gained after an earlier lookup" do
+      later_field = create(:work_package_custom_field)
+      work_package.available_custom_fields.to_a
+
+      type.default_variant.custom_field_ids |= [later_field.id]
+
+      expect(described_class.find(work_package.id).available_custom_fields).to include(later_field)
+    end
   end
 end
diff --git a/spec/workers/import/jira_create_project_work_packages_job_custom_fields_spec.rb b/spec/workers/import/jira_create_project_work_packages_job_custom_fields_spec.rb
index 95849b754afc..a442e1f83cd4 100644
--- a/spec/workers/import/jira_create_project_work_packages_job_custom_fields_spec.rb
+++ b/spec/workers/import/jira_create_project_work_packages_job_custom_fields_spec.rb
@@ -1049,6 +1049,44 @@ def jira_list_field(id:, name:, schema:, context_groups: nil)
     end
   end
 
+  describe "a field whose first value appears on a later issue of an already imported type" do
+    let!(:jira_field) do
+      create(:jira_field, jira_import:,
+                          origin_id: "customfield_10275",
+                          payload: {
+                            "id" => "customfield_10275",
+                            "name" => "CF Text",
+                            "schema" => {
+                              "type" => "string",
+                              "custom" => "com.atlassian.jira.plugin.system.customfieldtypes:textarea",
+                              "customId" => 10275
+                            }
+                          })
+    end
+    let!(:jira_issue_without_value) do
+      create(:jira_issue, jira_import:,
+                          origin_id: "10199",
+                          jira_project:,
+                          payload: issue_payload.deep_dup.tap do |payload|
+                            payload["key"] = "DYX-3"
+                            payload["fields"]["summary"] = "Issue without the text value"
+                            payload["fields"].delete("customfield_10275")
+                          end)
+    end
+    let!(:jira_issue) do
+      create(:jira_issue, jira_import:,
+                          origin_id: "10200",
+                          jira_project:,
+                          payload: issue_payload)
+    end
+
+    before { import_project }
+
+    it "sets the field's value on the issue that introduced it" do
+      expect(cf_value("CF Text")).to include("**bold**")
+    end
+  end
+
   describe "all custom field types in a single import run", with_ee: [:custom_field_hierarchies] do
     # Registers all field types at once and verifies the correct number of
     # OP custom fields are created: