diff --git a/enterprise/app/services/captain/audience_matcher.rb b/enterprise/app/services/captain/audience_matcher.rb
index 007960871..ba707e179 100644
--- a/enterprise/app/services/captain/audience_matcher.rb
+++ b/enterprise/app/services/captain/audience_matcher.rb
@@ -42,14 +42,14 @@ class Captain::AudienceMatcher
   def matches_leaf?(leaf)
     key = leaf[:attribute_key]
     actual = attribute_value(key)
-    expected = Array(leaf[:values]).first
+    values = Array(leaf[:values])
 
     case leaf[:filter_operator]
     when 'is_present'     then actual.present?
     when 'is_not_present' then actual.blank?
-    when 'equal_to'       then value_equal?(key, actual, expected)
-    when 'not_equal_to'   then !value_equal?(key, actual, expected)
-    else matches_text_or_range?(leaf[:filter_operator], actual, expected)
+    when 'equal_to'       then values.any? { |expected| value_equal?(key, actual, expected) }
+    when 'not_equal_to'   then values.none? { |expected| value_equal?(key, actual, expected) }
+    else matches_text_or_range?(leaf[:filter_operator], actual, values.first)
     end
   end
 
diff --git a/spec/enterprise/services/captain/audience_matcher_spec.rb b/spec/enterprise/services/captain/audience_matcher_spec.rb
index 279e0439c..2a6604007 100644
--- a/spec/enterprise/services/captain/audience_matcher_spec.rb
+++ b/spec/enterprise/services/captain/audience_matcher_spec.rb
@@ -77,6 +77,16 @@ RSpec.describe Captain::AudienceMatcher do
         expect(matches?(leaf('labels', 'equal_to', 'vip'))).to be(true)
         expect(matches?(leaf('labels', 'equal_to', 'enterprise'))).to be(false)
       end
+
+      it 'matches any of multiple selected labels' do
+        expect(matches?(leaf('labels', 'equal_to', %w[enterprise vip]))).to be(true)
+        expect(matches?(leaf('labels', 'equal_to', %w[enterprise smb]))).to be(false)
+      end
+
+      it 'not_equal_to rejects contacts carrying any selected label' do
+        expect(matches?(leaf('labels', 'not_equal_to', %w[enterprise vip]))).to be(false)
+        expect(matches?(leaf('labels', 'not_equal_to', %w[enterprise smb]))).to be(true)
+      end
     end
 
     context 'with conversation language fields' do