diff --git a/app/actions/deployment_create.rb b/app/actions/deployment_create.rb
index 67a92c6c60..d2b13e4481 100644
--- a/app/actions/deployment_create.rb
+++ b/app/actions/deployment_create.rb
@@ -83,7 +83,25 @@ def create(app:, user_audit_info:, message:)
 
         deployment
       rescue RevisionResolver::NoUpdateRollback, Sequel::ValidationFailed, AppStart::InvalidApp => e
-        error = DeploymentCreate::Error.new(e.message)
+        raise handle_deployment_create_error(e, app)
+      end
+
+      def handle_deployment_create_error(e, app)
+        space_quota_errors = %w[space_quota_exceeded space_app_instance_limit_exceeded]
+        org_quota_errors = %w[quota_exceeded app_instance_limit_exceeded]
+        space_error_msg = " for space #{app.space.name}. This space's quota may not be large enough to support rolling deployments or your configured max-in-flight."
+        org_error_msg_1 = " for organization #{app.organization.name}. "
+        org_error_msg_2 = "This organization's quota may not be large enough to support rolling deployments or your configured max-in-flight."
+        org_error_msg = org_error_msg_1 + org_error_msg_2
+        error_message = e.message
+
+        if space_quota_errors.any? { |substring| e.message.include?(substring) }
+          error_message += space_error_msg
+        elsif org_quota_errors.any? { |substring| e.message.include?(substring) }
+          error_message += org_error_msg
+        end
+
+        error = DeploymentCreate::Error.new(error_message)
         error.set_backtrace(e.backtrace)
         raise error
       end
diff --git a/spec/unit/actions/deployment_create_spec.rb b/spec/unit/actions/deployment_create_spec.rb
index 5f2f6cfa7f..0526d4bae4 100644
--- a/spec/unit/actions/deployment_create_spec.rb
+++ b/spec/unit/actions/deployment_create_spec.rb
@@ -605,6 +605,18 @@ module VCAP::CloudController
               end
             end
 
+            context 'when the app fails to start due to space errors' do
+              before do
+                allow(VCAP::CloudController::AppStart).to receive(:start).and_raise(VCAP::CloudController::AppStart::InvalidApp.new('memory space_quota_exceeded'))
+              end
+
+              it 'raises a DeploymentCreate::Error' do
+                error_msg_1 = "memory space_quota_exceeded for space #{app.space.name}. "
+                error_msg_2 = "This space's quota may not be large enough to support rolling deployments or your configured max-in-flight."
+                expect { DeploymentCreate.create(app:, message:, user_audit_info:) }.to raise_error(DeploymentCreate::Error, error_msg_1 + error_msg_2)
+              end
+            end
+
             context 'uses the web_instances from the message' do
               # stopped apps come up immediately and don't go through the deployment updater
               let(:web_instances) { 12 }
@@ -637,7 +649,9 @@ module VCAP::CloudController
                   let(:web_instances) { 11 }
 
                   it 'throws an error' do
-                    expect { DeploymentCreate.create(app:, message:, user_audit_info:) }.to raise_error(DeploymentCreate::Error, 'memory quota_exceeded')
+                    error_msg_1 = "memory quota_exceeded for organization #{app.organization.name}. "
+                    error_msg_2 = "This organization's quota may not be large enough to support rolling deployments or your configured max-in-flight."
+                    expect { DeploymentCreate.create(app:, message:, user_audit_info:) }.to raise_error(DeploymentCreate::Error, error_msg_1 + error_msg_2)
                   end
                 end
 
@@ -683,7 +697,9 @@ module VCAP::CloudController
                   let(:memory_in_mb) { 4000 }
 
                   it 'throws an error' do
-                    expect { DeploymentCreate.create(app:, message:, user_audit_info:) }.to raise_error(DeploymentCreate::Error, 'memory quota_exceeded')
+                    error_msg_1 = "memory quota_exceeded for organization #{app.organization.name}. "
+                    error_msg_2 = "This organization's quota may not be large enough to support rolling deployments or your configured max-in-flight."
+                    expect { DeploymentCreate.create(app:, message:, user_audit_info:) }.to raise_error(DeploymentCreate::Error, error_msg_1 + error_msg_2)
                   end
                 end
 
@@ -717,16 +733,6 @@ module VCAP::CloudController
                 expect(deployment.canary_steps).to eq([{ 'instance_weight' => 40 }, { 'instance_weight' => 80 }])
               end
             end
-
-            context 'when the app fails to start' do
-              before do
-                allow(VCAP::CloudController::AppStart).to receive(:start).and_raise(VCAP::CloudController::AppStart::InvalidApp.new('memory quota_exceeded'))
-              end
-
-              it 'raises a DeploymentCreate::Error' do
-                expect { DeploymentCreate.create(app:, message:, user_audit_info:) }.to raise_error(DeploymentCreate::Error, 'memory quota_exceeded')
-              end
-            end
           end
         end
 
@@ -880,7 +886,9 @@ module VCAP::CloudController
                 let(:web_instances) { 11 }
 
                 it 'throws an error' do
-                  expect { DeploymentCreate.create(app:, message:, user_audit_info:) }.to raise_error(DeploymentCreate::Error, 'memory quota_exceeded')
+                  error_msg_1 = "memory quota_exceeded for organization #{app.organization.name}. "
+                  error_msg_2 = "This organization's quota may not be large enough to support rolling deployments or your configured max-in-flight."
+                  expect { DeploymentCreate.create(app:, message:, user_audit_info:) }.to raise_error(DeploymentCreate::Error, error_msg_1 + error_msg_2)
                 end
               end
 
@@ -935,7 +943,9 @@ module VCAP::CloudController
                 let(:memory_in_mb) { 4000 }
 
                 it 'throws an error' do
-                  expect { DeploymentCreate.create(app:, message:, user_audit_info:) }.to raise_error(DeploymentCreate::Error, 'memory quota_exceeded')
+                  error_msg_1 = "memory quota_exceeded for organization #{app.organization.name}. "
+                  error_msg_2 = "This organization's quota may not be large enough to support rolling deployments or your configured max-in-flight."
+                  expect { DeploymentCreate.create(app:, message:, user_audit_info:) }.to raise_error(DeploymentCreate::Error, error_msg_1 + error_msg_2)
                 end
               end