diff --git a/lib/capybara/queries/selector_query.rb b/lib/capybara/queries/selector_query.rb
index 94f8c15f..e60c9295 100644
--- a/lib/capybara/queries/selector_query.rb
+++ b/lib/capybara/queries/selector_query.rb
@@ -60,14 +60,14 @@ module Capybara
         description(true)
       end
 
-      def matches_filters?(node)
+      def matches_filters?(node, node_filter_errors = [])
         return true if (@resolved_node&.== node) && options[:allow_self]
 
         applied_filters << :system
         return false unless matches_system_filters?(node)
 
         applied_filters << :node
-        matches_node_filters?(node) && matches_filter_block?(node)
+        matches_node_filters?(node, node_filter_errors) && matches_filter_block?(node)
       rescue *(node.respond_to?(:session) ? node.session.driver.invalid_element_errors : [])
         false
       end
@@ -163,21 +163,23 @@ module Capybara
         VALID_KEYS + custom_keys
       end
 
-      def matches_node_filters?(node)
+      def matches_node_filters?(node, errors)
         unapplied_options = options.keys - valid_keys
-        node_filters.all? do |filter_name, filter|
-          if filter.matcher?
-            unapplied_options.select { |option_name| filter.handles_option?(option_name) }.all? do |option_name|
-              unapplied_options.delete(option_name)
-              filter.matches?(node, option_name, options[option_name])
+        @selector.with_filter_errors(errors) do
+          node_filters.all? do |filter_name, filter|
+            if filter.matcher?
+              unapplied_options.select { |option_name| filter.handles_option?(option_name) }.all? do |option_name|
+                unapplied_options.delete(option_name)
+                filter.matches?(node, option_name, options[option_name], @selector)
+              end
+            elsif options.key?(filter_name)
+              unapplied_options.delete(filter_name)
+              filter.matches?(node, filter_name, options[filter_name], @selector)
+            elsif filter.default?
+              filter.matches?(node, filter_name, filter.default, @selector)
+            else
+              true
             end
-          elsif options.key?(filter_name)
-            unapplied_options.delete(filter_name)
-            filter.matches?(node, filter_name, options[filter_name])
-          elsif filter.default?
-            filter.matches?(node, filter_name, filter.default)
-          else
-            true
           end
         end
       end
@@ -268,13 +270,13 @@ module Capybara
           if ef.matcher?
             unapplied_options.select(&ef.method(:handles_option?)).inject(expr) do |memo, option_name|
               unapplied_options.delete(option_name)
-              ef.apply_filter(memo, option_name, options[option_name])
+              ef.apply_filter(memo, option_name, options[option_name], @selector)
             end
           elsif options.key?(name)
             unapplied_options.delete(name)
-            ef.apply_filter(expr, name, options[name])
+            ef.apply_filter(expr, name, options[name], @selector)
           elsif ef.default?
-            ef.apply_filter(expr, name, ef.default)
+            ef.apply_filter(expr, name, ef.default, @selector)
           else
             expr
           end
diff --git a/lib/capybara/result.rb b/lib/capybara/result.rb
index a43ec18c..f20c0ec1 100644
--- a/lib/capybara/result.rb
+++ b/lib/capybara/result.rb
@@ -28,7 +28,8 @@ module Capybara
     def initialize(elements, query)
       @elements = elements
       @result_cache = []
-      @results_enum = lazy_select_elements { |node| query.matches_filters?(node) }
+      @filter_errors = []
+      @results_enum = lazy_select_elements { |node| query.matches_filters?(node, @filter_errors) }
       @query = query
     end
 
@@ -113,7 +114,8 @@ module Capybara
       end
       unless rest.empty?
         elements = rest.map { |el| el.text rescue '<<ERROR>>' }.map(&:inspect).join(', ') # rubocop:disable Style/RescueModifier
-        message << '. Also found ' << elements << ', which matched the selector but not all filters.'
+        message << '. Also found ' << elements << ', which matched the selector but not all filters. '
+        message << @filter_errors.join('. ') if (rest.size == 1) && count.zero?
       end
       message
     end
diff --git a/lib/capybara/selector.rb b/lib/capybara/selector.rb
index d7b86c7b..80b7273e 100644
--- a/lib/capybara/selector.rb
+++ b/lib/capybara/selector.rb
@@ -59,7 +59,10 @@ Capybara.add_selector(:field) do
 
   node_filter(:readonly, :boolean) { |node, value| !(value ^ node.readonly?) }
   node_filter(:with) do |node, with|
-    with.is_a?(Regexp) ? node.value =~ with : node.value == with.to_s
+    val = node.value
+    (with.is_a?(Regexp) ? val =~ with : val == with.to_s).tap do |res|
+      add_error("Expected value to be #{with.inspect} but was #{val.inspect}") unless res
+    end
   end
 
   describe_expression_filters do |type: nil, **options|
@@ -109,7 +112,9 @@ Capybara.add_selector(:link) do
 
   node_filter(:href) do |node, href|
     # If not a Regexp it's been handled in the main XPath
-    href.is_a?(Regexp) ? node[:href].match(href) : true
+    (href.is_a?(Regexp) ? node[:href].match(href) : true).tap do |res|
+      add_error "Expected href to match #{href.inspect} but it was #{node[:href].inspect}" unless res
+    end
   end
 
   expression_filter(:download, valid_values: [true, false, String]) do |expr, download|
@@ -178,7 +183,9 @@ end
 Capybara.add_selector(:link_or_button) do
   label 'link or button'
   xpath do |locator, **options|
-    self.class.all.values_at(:link, :button).map { |selector| selector.call(locator, **options, selector_config: @config) }.reduce(:union)
+    self.class.all.values_at(:link, :button).map do |selector|
+      instance_exec(locator, options, &selector.xpath)
+    end.reduce(:union)
   end
 
   node_filter(:disabled, :boolean, default: false, skip_if: :all) { |node, value| node.tag_name == 'a' || !(value ^ node.disabled?) }
@@ -210,7 +217,10 @@ Capybara.add_selector(:fillable_field) do
   filter_set(:_field, %i[disabled multiple name placeholder])
 
   node_filter(:with) do |node, with|
-    with.is_a?(Regexp) ? node.value =~ with : node.value == with.to_s
+    val = node.value
+    (with.is_a?(Regexp) ? val =~ with : val == with.to_s).tap do |res|
+      add_error("Expected value to be #{with.inspect} but was #{val.inspect}") unless res
+    end
   end
 
   describe_expression_filters
@@ -231,7 +241,12 @@ Capybara.add_selector(:radio_button) do
 
   filter_set(:_field, %i[checked unchecked disabled name])
 
-  node_filter(:option) { |node, value| node.value == value.to_s }
+  node_filter(:option) do |node, value|
+    val = node.value
+    (val == value.to_s).tap do |res|
+      add_error("Expected option value to be #{value.inspect} but it was #{val.inspect}") unless res
+    end
+  end
 
   describe_expression_filters
   describe_node_filters do |option: nil, **|
@@ -249,7 +264,12 @@ Capybara.add_selector(:checkbox) do
 
   filter_set(:_field, %i[checked unchecked disabled name])
 
-  node_filter(:option) { |node, value| node.value == value.to_s }
+  node_filter(:option) do |node, value|
+    val = node.value
+    (val == value.to_s).tap do |res|
+      add_error("Expected option value to be #{value.inspect} but it was #{val.inspect}") unless res
+    end
+  end
 
   describe_expression_filters
   describe_node_filters do |option: nil, **|
@@ -273,7 +293,9 @@ Capybara.add_selector(:select) do
     else
       node.all(:xpath, './/option', visible: false, wait: false).map { |option| option.text(:all) }
     end
-    options.sort == actual.sort
+    (options.sort == actual.sort).tap do |res|
+      add_error("Expected options #{options.inspect} found #{actual.inspect}") unless res
+    end
   end
 
   expression_filter(:with_options) do |expr, options|
@@ -284,12 +306,16 @@ Capybara.add_selector(:select) do
 
   node_filter(:selected) do |node, selected|
     actual = node.all(:xpath, './/option', visible: false, wait: false).select(&:selected?).map { |option| option.text(:all) }
-    Array(selected).sort == actual.sort
+    (Array(selected).sort == actual.sort).tap do |res|
+      add_error("Expected #{selected.inspect} to be selected found #{actual.inspect}") unless res
+    end
   end
 
   node_filter(:with_selected) do |node, selected|
     actual = node.all(:xpath, './/option', visible: false, wait: false).select(&:selected?).map { |option| option.text(:all) }
-    (Array(selected) - actual).empty?
+    (Array(selected) - actual).empty?.tap do |res|
+      add_error("Expected at least #{selected.inspect} to be selected found #{actual.inspect}") unless res
+    end
   end
 
   describe_expression_filters do |with_options: nil, **opts|
@@ -320,7 +346,9 @@ Capybara.add_selector(:datalist_input) do
 
   node_filter(:options) do |node, options|
     actual = node.find("//datalist[@id=#{node[:list]}]", visible: :all).all(:datalist_option, wait: false).map(&:value)
-    options.sort == actual.sort
+    (options.sort == actual.sort).tap do |res|
+      add_error("Expected #{options.inspect} options found #{actual.inspect}") unless res
+    end
   end
 
   expression_filter(:with_options) do |expr, options|
@@ -471,7 +499,11 @@ Capybara.add_selector(:element) do
   end
 
   node_filter(:attributes, matcher: /.+/) do |node, name, val|
-    val.is_a?(Regexp) ? node[name] =~ val : true
+    next true unless val.is_a?(Regexp)
+
+    (node[name] =~ val).tap do |res|
+      add_error("Expected #{name} to match #{val.inspect} but it was #{node[name]}") unless res
+    end
   end
 
   describe_expression_filters do |**options|
diff --git a/lib/capybara/selector/filters/base.rb b/lib/capybara/selector/filters/base.rb
index 3cd6acc0..5d2ad0cb 100644
--- a/lib/capybara/selector/filters/base.rb
+++ b/lib/capybara/selector/filters/base.rb
@@ -7,18 +7,9 @@ module Capybara
         def initialize(name, matcher, block, **options)
           @name = name
           @matcher = matcher
+          @block = block
           @options = options
           @options[:valid_values] = [true, false] if options[:boolean]
-          @block = if boolean?
-            proc do |node, value|
-              error_cnt = errors.size
-              block.call(node, value).tap do |res|
-                add_error("Expected #{@name} #{value} but it wasn't") if !res && error_cnt == errors.size
-              end
-            end
-          else
-            block
-          end
         end
 
         def default?
diff --git a/lib/capybara/selector/filters/node_filter.rb b/lib/capybara/selector/filters/node_filter.rb
index 73f0b289..2731bdf6 100644
--- a/lib/capybara/selector/filters/node_filter.rb
+++ b/lib/capybara/selector/filters/node_filter.rb
@@ -6,7 +6,21 @@ module Capybara
   class Selector
     module Filters
       class NodeFilter < Base
-        def matches?(node, name, value, context=nil)
+        def initialize(name, matcher, block, **options)
+          super
+          @block = if boolean?
+            proc do |node, value|
+              error_cnt = errors.size
+              block.call(node, value).tap do |res|
+                add_error("Expected #{name} #{value} but it wasn't") if !res && error_cnt == errors.size
+              end
+            end
+          else
+            block
+          end
+        end
+
+        def matches?(node, name, value, context = nil)
           apply(node, name, value, true, context)
         rescue Capybara::ElementNotFound
           false
diff --git a/lib/capybara/selector/selector.rb b/lib/capybara/selector/selector.rb
index 973d7d36..6c4a3729 100644
--- a/lib/capybara/selector/selector.rb
+++ b/lib/capybara/selector/selector.rb
@@ -389,6 +389,10 @@ module Capybara
       vis.nil? ? fallback : vis
     end
 
+    def add_error(error_msg)
+      errors << error_msg
+    end
+
     # @api private
     def builder
       case format
@@ -401,8 +405,20 @@ module Capybara
       end
     end
 
+    # @api private
+    def with_filter_errors(errors)
+      Thread.current["capybara_#{object_id}_errors"] = errors
+      yield
+    ensure
+      Thread.current["capybara_#{object_id}_errors"] = nil
+    end
+
   private
 
+    def errors
+      Thread.current["capybara_#{object_id}_errors"] || []
+    end
+
     def enable_aria_label
       @config[:enable_aria_label]
     end
diff --git a/lib/capybara/spec/session/has_field_spec.rb b/lib/capybara/spec/session/has_field_spec.rb
index e0111b0e..0530af77 100644
--- a/lib/capybara/spec/session/has_field_spec.rb
+++ b/lib/capybara/spec/session/has_field_spec.rb
@@ -41,6 +41,23 @@ Capybara::SpecHelper.spec '#has_field' do
       expect(@session).not_to have_field('First Name', with: 'John')
       expect(@session).not_to have_field('First Name', with: /John|Paul|George|Ringo/)
     end
+
+    it 'should output filter errors if only one element matched the selector but failed the filters' do
+      @session.fill_in('First Name', with: 'Thomas')
+      expect do
+        expect(@session).to have_field('First Name', with: 'Jonas')
+      end.to raise_exception(RSpec::Expectations::ExpectationNotMetError, /Expected value to be "Jonas" but was "Thomas"/)
+
+      # native boolean node filter
+      expect do
+        expect(@session).to have_field('First Name', readonly: true)
+      end.to raise_exception(RSpec::Expectations::ExpectationNotMetError, /Expected readonly true but it wasn't/)
+
+      # inherited boolean node filter
+      expect do
+        expect(@session).to have_field('form_pets_cat', checked: true)
+      end.to raise_exception(RSpec::Expectations::ExpectationNotMetError, /Expected checked true but it wasn't/)
+    end
   end
 
   context 'with type' do