diff --git a/lib/capybara/selector/regexp_disassembler.rb b/lib/capybara/selector/regexp_disassembler.rb
index f749cfb8..9b24c99b 100644
--- a/lib/capybara/selector/regexp_disassembler.rb
+++ b/lib/capybara/selector/regexp_disassembler.rb
@@ -12,18 +12,48 @@ module Capybara
 
       def alternated_substrings
         @alternated_substrings ||= begin
-          process(alternation: true)
+          or_strings = process(alternation: true)
+          remove_or_covered(or_strings)
+          or_strings.any?(&:empty?) ? [] : or_strings
         end
       end
 
       def substrings
         @substrings ||= begin
-          process(alternation: false).first
+          strs = process(alternation: false).first
+          remove_and_covered(strs)
         end
       end
 
     private
 
+      def remove_and_covered(strings)
+        # If we have "ab" and "abcd" required - only need to check for "abcd"
+        strings.delete_if do |sub_string|
+          strings.any? do |cover_string|
+            next if sub_string.equal? cover_string
+
+            cover_string.include?(sub_string)
+          end
+        end
+      end
+
+      def remove_or_covered(or_series)
+        # If we are going to match `("a" and "b") or ("ade" and "bce")` it only makes sense to match ("a" and "b")
+
+        # Ensure minimum sets of strings are being or'd
+        or_series.each { |strs| remove_and_covered(strs) }
+
+        # Remove any of the alternated string series that fully contain any other string series
+        or_series.delete_if do |and_strs|
+          or_series.any? do |and_strs2|
+            next if and_strs.equal? and_strs2
+
+            remove_and_covered(and_strs + and_strs2) == and_strs
+          end
+        end
+      end
+
       def process(alternation:)
         strs = extract_strings(Regexp::Parser.parse(@regexp), alternation: alternation)
         strs = collapse(combine(strs).map(&:flatten))
@@ -68,8 +98,8 @@ module Capybara
       end
 
       def extract_strings(expression, strings = [], alternation: false)
-        expression.each do |exp|
-          if optional?(exp)
+        expression.each do |exp| # rubocop:disable Metrics/BlockLength
+          if optional?(exp) && !(alternation && zero_or_one?(exp))
             strings.push(nil)
             next
           end
@@ -87,12 +117,25 @@ module Capybara
           if exp.terminal?
             case exp.type
             when :literal
-              strings.push(exp.text * min_repeat(exp))
+              if zero_or_one?(exp)
+                strings.push(Set.new([[''], [exp.text]]))
+                next
+              else
+                strings.push(exp.text * min_repeat(exp))
+              end
             when :escape
-              strings.push(exp.char * min_repeat(exp))
+              if zero_or_one?(exp)
+                strings.push(Set.new([[''], [exp.text]]))
+                next
+              else
+                strings.push(exp.char * min_repeat(exp))
+              end
             else
               strings.push(nil)
             end
+          elsif alternation && zero_or_one?(exp)
+            strings.push(Set.new([[''], extract_strings(exp, alternation: true)]))
+            next
           else
             min_repeat(exp).times { extract_strings(exp, strings, alternation: alternation) }
           end
@@ -101,6 +144,10 @@ module Capybara
         strings
       end
 
+      def zero_or_one?(exp)
+        exp.quantity == [0, 1]
+      end
+
       def alternative_strings(expression)
         alternatives = expression.alternatives.map { |sub_exp| extract_strings(sub_exp, alternation: true) }
         if alternatives.all?(&:any?)
diff --git a/spec/regexp_dissassembler_spec.rb b/spec/regexp_dissassembler_spec.rb
index 58e8590e..542555f4 100644
--- a/spec/regexp_dissassembler_spec.rb
+++ b/spec/regexp_dissassembler_spec.rb
@@ -27,18 +27,37 @@ RSpec.describe Capybara::Selector::RegexpDisassembler do
       /abc./ => %w[abc],
       /abc.*/ => %w[abc],
       /abc.def/ => %w[abc def],
-      /abc.def.ghi/ => %w[abc def ghi]
+      /abc.def.ghi/ => %w[abc def ghi],
+      /abc.abcd.abcde/ => %w[abcde],
+      /.*/ => []
     )
   end
 
-  it 'handles optional characters' do
-    verify_strings(
+  it 'ignores optional characters for substrings' do
+    {
       /abc*def/ => %w[ab def],
       /abc*/ => %w[ab],
+      /c*/ => [],
       /abc?def/ => %w[ab def],
       /abc?/ => %w[ab],
       /abc?def?/ => %w[ab de],
-      /abc?def?g/ => %w[ab de g]
+      /abc?def?g/ => %w[ab de g],
+      /d?/ => []
+    }.each do |regexp, expected|
+      expect(Capybara::Selector::RegexpDisassembler.new(regexp).substrings).to eq expected
+    end
+  end
+
+  it 'handles optional characters for #alternated_substrings' do
+    verify_alternated_strings(
+      /abc*def/ => [%w[ab def]],
+      /abc*/ => [%w[ab]],
+      /c*/ => [],
+      /abc?def/ => [%w[abdef], %w[abcdef]],
+      /abc?/ => [%w[ab]],
+      /abc?def?/ => [%w[abde], %w[abcde]],
+      /abc?def?g/ => [%w[abdeg], %w[abdefg], %w[abcdeg], %w[abcdefg]],
+      /d?/ => []
     )
   end
 
@@ -111,24 +130,31 @@ RSpec.describe Capybara::Selector::RegexpDisassembler do
     end
   end
 
-  it 'handles alternation for #options' do
+  it 'handles alternation for #alternated_substrings' do
     verify_alternated_strings(
       /abc|def/ => [%w[abc], %w[def]],
       /ab(?:c|d)/ => [%w[abc], %w[abd]],
       /ab(c|d|e)fg/ => [%w[abcfg], %w[abdfg], %w[abefg]],
-      /ab?(c|d)fg/ => [%w[a cfg], %w[a dfg]],
+      /ab?(c|d)fg/ => [%w[acfg], %w[adfg], %w[abcfg], %w[abdfg]],
       /ab(c|d)ef/ => [%w[abcef], %w[abdef]],
-      /ab(cd?|ef)g/ => [%w[abc g], %w[abefg]],
+      /ab(cd?|ef)g/ => [%w[abcg], %w[abcdg], %w[abefg]],
       /ab(cd|ef*)g/ => [%w[abcdg], %w[abe g]],
       /ab|cd*/ => [%w[ab], %w[c]],
       /cd(?:ef|gh)|xyz/ => [%w[cdef], %w[cdgh], %w[xyz]],
       /(cd(?:ef|gh)|xyz)/ => [%w[cdef], %w[cdgh], %w[xyz]],
       /cd(ef|gh)+/ => [%w[cdef], %w[cdgh]],
       /cd(ef|gh)?/ => [%w[cd]],
-      /cd(ef|gh)?ij/ => [%w[cd ij]],
+      /cd(ef|gh)?ij/ => [%w[cdij], %w[cdefij], %w[cdghij]],
       /cd(ef|gh)+ij/ => [%w[cdef ij], %w[cdgh ij]],
       /cd(ef|gh){2}ij/ => [%w[cdefefij], %w[cdefghij], %w[cdghefij], %w[cdghghij]],
-      /(cd(ef|g*))/ => [%w[cd]]
+      /(cd(ef|g*))/ => [%w[cd]],
+      /a|b*/ => [],
+      /ab(?:c|d?)/ => [%w[ab]],
+      /ab(c|d)|a*/ => [],
+      /(abc)?(d|e)/ => [%w[d], %w[e]],
+      /(abc*de)?(d|e)/ => [%w[d], %w[e]],
+      /(abc*de)?(d|e?)/ => [],
+      /(abc)?(d|e?)/ => []
     )
   end
 
@@ -193,7 +219,7 @@ RSpec.describe Capybara::Selector::RegexpDisassembler do
 
   def verify_alternated_strings(hsh, wrap: false)
     hsh.each do |regexp, expected|
-      expected = [expected] if wrap
+      expected = [expected] if wrap && (expected != [])
       expect(Capybara::Selector::RegexpDisassembler.new(regexp).alternated_substrings).to eq expected
     end
   end