diff --git a/Gemfile.lock b/Gemfile.lock
index 2587edf8779..3d007a717dd 100644
--- a/Gemfile.lock
+++ b/Gemfile.lock
@@ -448,7 +448,7 @@ GEM
     compare-xml (0.66)
       nokogiri (~> 1.8)
     concurrent-ruby (1.3.4)
-    connection_pool (2.5.0)
+    connection_pool (2.5.1)
     cookiejar (0.3.4)
     cose (1.3.1)
       cbor (~> 0.5.9)
@@ -759,7 +759,7 @@ GEM
     loofah (2.24.0)
       crass (~> 1.0.2)
       nokogiri (>= 1.12.0)
-    lookbook (2.3.8)
+    lookbook (2.3.9)
       activemodel
       css_parser
       htmlbeautifier (~> 1.3)
@@ -1563,7 +1563,7 @@ CHECKSUMS
   commonmarker (2.3.0-x86_64-linux-musl) sha256=af895be1dfe723a1ae2671fd147d082e1be107be732b7a52e2e0d5daa1ae687a
   compare-xml (0.66) sha256=e21aa5c0f69ef1177eced997c688fd4df989084e74a1b612257af32e1dd05319
   concurrent-ruby (1.3.4) sha256=d4aa926339b0a86b5b5054a0a8c580163e6f5dcbdfd0f4bb916b1a2570731c32
-  connection_pool (2.5.0) sha256=233b92f8d38e038c1349ccea65dd3772727d669d6d2e71f9897c8bf5cd53ebfc
+  connection_pool (2.5.1) sha256=ae802a90a4b5a081101b39d618e69921a9a50bea9ac3420a5b8c71f1befa3e9c
   cookiejar (0.3.4) sha256=11b16acfc4baf7a0f463c21a6212005e04e25f5554d4d9f24d97f3492dfda0df
   cose (1.3.1) sha256=d5d4dbcd6b035d513edc4e1ab9bc10e9ce13b4011c96e3d1b8fe5e6413fd6de5
   costs (1.0.0)
@@ -1694,7 +1694,7 @@ CHECKSUMS
   logger (1.7.0) sha256=196edec7cc44b66cfb40f9755ce11b392f21f7967696af15d274dde7edff0203
   lograge (0.14.0) sha256=42371a75823775f166f727639f5ddce73dd149452a55fc94b90c303213dc9ae1
   loofah (2.24.0) sha256=61e6a710883abb8210887f3dc868cf3ed66594c509d9ff6987621efa6651ee1e
-  lookbook (2.3.8) sha256=8fe719b5f80a1f245074d94474fa16f2c102a388d93576f43ed0ba2244f1dc41
+  lookbook (2.3.9) sha256=b91fd92bd20281b87fbd23d7b22ffacb83ceb086c30986ab90275d220eaf0f39
   mail (2.8.1) sha256=ec3b9fadcf2b3755c78785cb17bc9a0ca9ee9857108a64b6f5cfc9c0b5bfc9ad
   marcel (1.0.4) sha256=0d5649feb64b8f19f3d3468b96c680bae9746335d02194270287868a661516a4
   markly (0.13.0) sha256=326a232c876cd95093d110b8d184be8effeadd776c3ffcefd59bdc8de7f59e0d
diff --git a/lib/open_project/patches/lookbook_tree_node_inflector.rb b/lib/open_project/patches/lookbook_tree_node_inflector.rb
index 189d41f4f21..1111c83afb7 100644
--- a/lib/open_project/patches/lookbook_tree_node_inflector.rb
+++ b/lib/open_project/patches/lookbook_tree_node_inflector.rb
@@ -41,7 +41,7 @@ module OpenProject
 end
 
 if Rails.env.local?
-  OpenProject::Patches.patch_gem_version "lookbook", "2.3.8" do
+  OpenProject::Patches.patch_gem_version "lookbook", "2.3.9" do
     Lookbook::TreeNode.prepend OpenProject::Patches::LookbookTreeNodeInflector
   end
 end
diff --git a/spec/features/principals/shared_memberships_examples.rb b/spec/features/principals/shared_memberships_examples.rb
index 0657a15bf0c..46010ac476f 100644
--- a/spec/features/principals/shared_memberships_examples.rb
+++ b/spec/features/principals/shared_memberships_examples.rb
@@ -20,6 +20,8 @@ RSpec.shared_examples "principal membership management flows" do
     member = principal.memberships.where(project_id: project.id).first
     principal_page.edit_roles!(member, %w(Manager Developer))
 
+    principal_page.expect_and_dismiss_flash(message: "Successful update")
+
     # Modify roles
     principal_page.expect_project(project.name)
     principal_page.expect_roles(project.name, %w(Manager Developer))
@@ -30,7 +32,7 @@ RSpec.shared_examples "principal membership management flows" do
     principal_page.expect_project(project.name)
     principal_page.edit_roles!(member, %w())
 
-    expect_flash(type: :error, message: "Roles need to be assigned.")
+    principal_page.expect_flash(type: :error, message: "Roles need to be assigned.")
 
     # Remove the user from the project
     principal_page.remove_from_project!(project.name)