diff --git a/lib/posthog/feature_flags.rb b/lib/posthog/feature_flags.rb
index 3e5d3c3..5d8c0b7 100644
--- a/lib/posthog/feature_flags.rb
+++ b/lib/posthog/feature_flags.rb
@@ -422,6 +422,103 @@ def self.relative_date_parse_for_feature_flag_matching(value)
       parsed_dt
     end
 
+    # Parse a semver string into a comparable [major, minor, patch] integer array.
+    # Handles v-prefix, whitespace, pre-release suffixes. Defaults missing components to 0.
+    def self.parse_semver(value)
+      raise InconclusiveMatchError, 'Invalid semver format' if value.nil?
+
+      text = value.to_s.strip.sub(/^[vV]/, '')
+
+      raise InconclusiveMatchError, 'Invalid semver format' if text.empty?
+
+      # Strip pre-release and build metadata suffixes
+      text = text.split('-')[0].split('+')[0]
+      parts = text.split('.')
+
+      raise InconclusiveMatchError, 'Invalid semver format' if parts.empty? || parts[0].to_s.empty?
+
+      # Check for leading dot or non-numeric parts
+      parts.each do |part|
+        raise InconclusiveMatchError, 'Invalid semver format' if part.empty? || part !~ /^\d+$/
+      end
+
+      major = parts[0].to_i
+      minor = parts.length > 1 ? parts[1].to_i : 0
+      patch = parts.length > 2 ? parts[2].to_i : 0
+
+      [major, minor, patch]
+    end
+
+    # Returns bounds for tilde (~) range:
+    # ~X       → >=X.0.0 <(X+1).0.0
+    # ~X.Y     → >=X.Y.0 <X.(Y+1).0
+    # ~X.Y.Z   → >=X.Y.Z <X.(Y+1).0
+    def self.semver_tilde_bounds(value)
+      major, minor, patch = parse_semver(value)
+      lower = [major, minor, patch]
+
+      # Determine how many components were provided
+      text = value.to_s.strip.sub(/^[vV]/, '')
+      text = text.split('-')[0].split('+')[0]
+      component_count = text.split('.').length
+
+      upper = if component_count == 1
+                # Major-only: bump major
+                [major + 1, 0, 0]
+              else
+                # Major.minor or major.minor.patch: bump minor
+                [major, minor + 1, 0]
+              end
+
+      [lower, upper]
+    end
+
+    # Returns bounds for caret (^) range per semver spec:
+    # ^X.Y.Z where X > 0 → >=X.Y.Z <(X+1).0.0
+    # ^0.Y.Z where Y > 0 → >=0.Y.Z <0.(Y+1).0
+    # ^0.0.Z → >=0.0.Z <0.0.(Z+1)
+    def self.semver_caret_bounds(value)
+      major, minor, patch = parse_semver(value)
+      lower = [major, minor, patch]
+
+      upper = if major.positive?
+                [major + 1, 0, 0]
+              elsif minor.positive?
+                [0, minor + 1, 0]
+              else
+                [0, 0, patch + 1]
+              end
+
+      [lower, upper]
+    end
+
+    # Returns bounds for wildcard (*) range:
+    # X.* or X → >=X.0.0 <(X+1).0.0
+    # X.Y.* → >=X.Y.0 <X.(Y+1).0
+    def self.semver_wildcard_bounds(value)
+      cleaned = value.to_s.strip.sub(/^[vV]/, '').gsub('*', '').chomp('.')
+      parts = cleaned.split('.').reject(&:empty?)
+
+      raise InconclusiveMatchError, 'Invalid semver wildcard format' if parts.empty?
+
+      parts.each do |part|
+        raise InconclusiveMatchError, 'Invalid semver wildcard format' if part !~ /^\d+$/
+      end
+
+      major = parts[0].to_i
+      case parts.length
+      when 1
+        [[major, 0, 0], [major + 1, 0, 0]]
+      when 2
+        minor = parts[1].to_i
+        [[major, minor, 0], [major, minor + 1, 0]]
+      else
+        minor = parts[1].to_i
+        patch = parts[2].to_i
+        [[major, minor, patch], [major, minor, patch + 1]]
+      end
+    end
+
     def self.match_property(property, property_values, cohort_properties = {})
       # only looks for matches where key exists in property_values
       # doesn't support operator is_not_set
@@ -496,6 +593,36 @@ def self.match_property(property, property_values, cohort_properties = {})
         elsif operator == 'is_date_after'
           override_date > parsed_date
         end
+      when 'semver_eq', 'semver_neq', 'semver_gt', 'semver_gte', 'semver_lt', 'semver_lte'
+        override_parsed = parse_semver(override_value)
+        flag_parsed = parse_semver(value)
+
+        case operator
+        when 'semver_eq'
+          override_parsed == flag_parsed
+        when 'semver_neq'
+          override_parsed != flag_parsed
+        when 'semver_gt'
+          (override_parsed <=> flag_parsed) == 1
+        when 'semver_gte'
+          (override_parsed <=> flag_parsed) >= 0
+        when 'semver_lt'
+          (override_parsed <=> flag_parsed) == -1
+        when 'semver_lte'
+          (override_parsed <=> flag_parsed) <= 0
+        end
+      when 'semver_tilde'
+        override_parsed = parse_semver(override_value)
+        lower, upper = semver_tilde_bounds(value)
+        (override_parsed <=> lower) >= 0 && (override_parsed <=> upper) == -1
+      when 'semver_caret'
+        override_parsed = parse_semver(override_value)
+        lower, upper = semver_caret_bounds(value)
+        (override_parsed <=> lower) >= 0 && (override_parsed <=> upper) == -1
+      when 'semver_wildcard'
+        override_parsed = parse_semver(override_value)
+        lower, upper = semver_wildcard_bounds(value)
+        (override_parsed <=> lower) >= 0 && (override_parsed <=> upper) == -1
       else
         raise InconclusiveMatchError, "Unknown operator: #{operator}"
       end
diff --git a/spec/posthog/feature_flag_spec.rb b/spec/posthog/feature_flag_spec.rb
index 60f83bd..1f72000 100644
--- a/spec/posthog/feature_flag_spec.rb
+++ b/spec/posthog/feature_flag_spec.rb
@@ -1566,6 +1566,256 @@ module PostHog
         expect(e.message).to eq('Unknown operator: is_unknown')
       end
     end
+
+    # Semver operator tests
+    it 'with semver_eq operator' do
+      property = { 'key' => 'version', 'value' => '1.2.3', 'operator' => 'semver_eq' }
+      expect(FeatureFlagsPoller.match_property(property, { 'version' => '1.2.3' })).to be true
+      expect(FeatureFlagsPoller.match_property(property, { 'version' => '1.2.4' })).to be false
+      expect(FeatureFlagsPoller.match_property(property, { 'version' => '1.2.2' })).to be false
+      expect(FeatureFlagsPoller.match_property(property, { 'version' => '2.0.0' })).to be false
+    end
+
+    it 'with semver_neq operator' do
+      property = { 'key' => 'version', 'value' => '1.2.3', 'operator' => 'semver_neq' }
+      expect(FeatureFlagsPoller.match_property(property, { 'version' => '1.2.3' })).to be false
+      expect(FeatureFlagsPoller.match_property(property, { 'version' => '1.2.4' })).to be true
+      expect(FeatureFlagsPoller.match_property(property, { 'version' => '1.2.2' })).to be true
+      expect(FeatureFlagsPoller.match_property(property, { 'version' => '2.0.0' })).to be true
+    end
+
+    it 'with semver_gt operator' do
+      property = { 'key' => 'version', 'value' => '1.2.3', 'operator' => 'semver_gt' }
+      expect(FeatureFlagsPoller.match_property(property, { 'version' => '1.2.4' })).to be true
+      expect(FeatureFlagsPoller.match_property(property, { 'version' => '1.3.0' })).to be true
+      expect(FeatureFlagsPoller.match_property(property, { 'version' => '2.0.0' })).to be true
+      expect(FeatureFlagsPoller.match_property(property, { 'version' => '1.2.3' })).to be false
+      expect(FeatureFlagsPoller.match_property(property, { 'version' => '1.2.2' })).to be false
+      expect(FeatureFlagsPoller.match_property(property, { 'version' => '0.9.9' })).to be false
+    end
+
+    it 'with semver_gte operator' do
+      property = { 'key' => 'version', 'value' => '1.2.3', 'operator' => 'semver_gte' }
+      expect(FeatureFlagsPoller.match_property(property, { 'version' => '1.2.3' })).to be true
+      expect(FeatureFlagsPoller.match_property(property, { 'version' => '1.2.4' })).to be true
+      expect(FeatureFlagsPoller.match_property(property, { 'version' => '1.3.0' })).to be true
+      expect(FeatureFlagsPoller.match_property(property, { 'version' => '2.0.0' })).to be true
+      expect(FeatureFlagsPoller.match_property(property, { 'version' => '1.2.2' })).to be false
+      expect(FeatureFlagsPoller.match_property(property, { 'version' => '0.9.9' })).to be false
+    end
+
+    it 'with semver_lt operator' do
+      property = { 'key' => 'version', 'value' => '1.2.3', 'operator' => 'semver_lt' }
+      expect(FeatureFlagsPoller.match_property(property, { 'version' => '1.2.2' })).to be true
+      expect(FeatureFlagsPoller.match_property(property, { 'version' => '1.1.0' })).to be true
+      expect(FeatureFlagsPoller.match_property(property, { 'version' => '0.9.9' })).to be true
+      expect(FeatureFlagsPoller.match_property(property, { 'version' => '1.2.3' })).to be false
+      expect(FeatureFlagsPoller.match_property(property, { 'version' => '1.2.4' })).to be false
+      expect(FeatureFlagsPoller.match_property(property, { 'version' => '2.0.0' })).to be false
+    end
+
+    it 'with semver_lte operator' do
+      property = { 'key' => 'version', 'value' => '1.2.3', 'operator' => 'semver_lte' }
+      expect(FeatureFlagsPoller.match_property(property, { 'version' => '1.2.3' })).to be true
+      expect(FeatureFlagsPoller.match_property(property, { 'version' => '1.2.2' })).to be true
+      expect(FeatureFlagsPoller.match_property(property, { 'version' => '1.1.0' })).to be true
+      expect(FeatureFlagsPoller.match_property(property, { 'version' => '0.9.9' })).to be true
+      expect(FeatureFlagsPoller.match_property(property, { 'version' => '1.2.4' })).to be false
+      expect(FeatureFlagsPoller.match_property(property, { 'version' => '2.0.0' })).to be false
+    end
+
+    it 'with semver_tilde operator' do
+      # ~1.2.3 means >=1.2.3 <1.3.0
+      property = { 'key' => 'version', 'value' => '1.2.3', 'operator' => 'semver_tilde' }
+      expect(FeatureFlagsPoller.match_property(property, { 'version' => '1.2.3' })).to be true
+      expect(FeatureFlagsPoller.match_property(property, { 'version' => '1.2.4' })).to be true
+      expect(FeatureFlagsPoller.match_property(property, { 'version' => '1.2.99' })).to be true
+      expect(FeatureFlagsPoller.match_property(property, { 'version' => '1.2.2' })).to be false
+      expect(FeatureFlagsPoller.match_property(property, { 'version' => '1.3.0' })).to be false
+      expect(FeatureFlagsPoller.match_property(property, { 'version' => '1.3.1' })).to be false
+      expect(FeatureFlagsPoller.match_property(property, { 'version' => '2.0.0' })).to be false
+
+      # Test boundary values
+      property2 = { 'key' => 'version', 'value' => '1.0.0', 'operator' => 'semver_tilde' }
+      expect(FeatureFlagsPoller.match_property(property2, { 'version' => '1.0.0' })).to be true
+      expect(FeatureFlagsPoller.match_property(property2, { 'version' => '1.0.99' })).to be true
+      expect(FeatureFlagsPoller.match_property(property2, { 'version' => '1.1.0' })).to be false
+
+      # Major-only tilde: ~1 means >=1.0.0 <2.0.0
+      property3 = { 'key' => 'version', 'value' => '1', 'operator' => 'semver_tilde' }
+      expect(FeatureFlagsPoller.match_property(property3, { 'version' => '1.0.0' })).to be true
+      expect(FeatureFlagsPoller.match_property(property3, { 'version' => '1.5.0' })).to be true
+      expect(FeatureFlagsPoller.match_property(property3, { 'version' => '1.99.99' })).to be true
+      expect(FeatureFlagsPoller.match_property(property3, { 'version' => '0.9.9' })).to be false
+      expect(FeatureFlagsPoller.match_property(property3, { 'version' => '2.0.0' })).to be false
+    end
+
+    it 'with semver_caret operator' do
+      # ^1.2.3 means >=1.2.3 <2.0.0 (major > 0)
+      property = { 'key' => 'version', 'value' => '1.2.3', 'operator' => 'semver_caret' }
+      expect(FeatureFlagsPoller.match_property(property, { 'version' => '1.2.3' })).to be true
+      expect(FeatureFlagsPoller.match_property(property, { 'version' => '1.2.4' })).to be true
+      expect(FeatureFlagsPoller.match_property(property, { 'version' => '1.3.0' })).to be true
+      expect(FeatureFlagsPoller.match_property(property, { 'version' => '1.99.99' })).to be true
+      expect(FeatureFlagsPoller.match_property(property, { 'version' => '1.2.2' })).to be false
+      expect(FeatureFlagsPoller.match_property(property, { 'version' => '2.0.0' })).to be false
+      expect(FeatureFlagsPoller.match_property(property, { 'version' => '0.9.9' })).to be false
+
+      # ^0.2.3 means >=0.2.3 <0.3.0 (major == 0, minor > 0)
+      property2 = { 'key' => 'version', 'value' => '0.2.3', 'operator' => 'semver_caret' }
+      expect(FeatureFlagsPoller.match_property(property2, { 'version' => '0.2.3' })).to be true
+      expect(FeatureFlagsPoller.match_property(property2, { 'version' => '0.2.4' })).to be true
+      expect(FeatureFlagsPoller.match_property(property2, { 'version' => '0.2.99' })).to be true
+      expect(FeatureFlagsPoller.match_property(property2, { 'version' => '0.2.2' })).to be false
+      expect(FeatureFlagsPoller.match_property(property2, { 'version' => '0.3.0' })).to be false
+      expect(FeatureFlagsPoller.match_property(property2, { 'version' => '1.0.0' })).to be false
+
+      # ^0.0.3 means >=0.0.3 <0.0.4 (major == 0, minor == 0)
+      property3 = { 'key' => 'version', 'value' => '0.0.3', 'operator' => 'semver_caret' }
+      expect(FeatureFlagsPoller.match_property(property3, { 'version' => '0.0.3' })).to be true
+      expect(FeatureFlagsPoller.match_property(property3, { 'version' => '0.0.2' })).to be false
+      expect(FeatureFlagsPoller.match_property(property3, { 'version' => '0.0.4' })).to be false
+      expect(FeatureFlagsPoller.match_property(property3, { 'version' => '0.1.0' })).to be false
+    end
+
+    it 'with semver_wildcard operator' do
+      # 1.2.* means >=1.2.0 <1.3.0
+      property = { 'key' => 'version', 'value' => '1.2.*', 'operator' => 'semver_wildcard' }
+      expect(FeatureFlagsPoller.match_property(property, { 'version' => '1.2.0' })).to be true
+      expect(FeatureFlagsPoller.match_property(property, { 'version' => '1.2.3' })).to be true
+      expect(FeatureFlagsPoller.match_property(property, { 'version' => '1.2.99' })).to be true
+      expect(FeatureFlagsPoller.match_property(property, { 'version' => '1.1.9' })).to be false
+      expect(FeatureFlagsPoller.match_property(property, { 'version' => '1.3.0' })).to be false
+      expect(FeatureFlagsPoller.match_property(property, { 'version' => '2.0.0' })).to be false
+
+      # 1.* means >=1.0.0 <2.0.0
+      property2 = { 'key' => 'version', 'value' => '1.*', 'operator' => 'semver_wildcard' }
+      expect(FeatureFlagsPoller.match_property(property2, { 'version' => '1.0.0' })).to be true
+      expect(FeatureFlagsPoller.match_property(property2, { 'version' => '1.2.3' })).to be true
+      expect(FeatureFlagsPoller.match_property(property2, { 'version' => '1.99.99' })).to be true
+      expect(FeatureFlagsPoller.match_property(property2, { 'version' => '0.9.9' })).to be false
+      expect(FeatureFlagsPoller.match_property(property2, { 'version' => '2.0.0' })).to be false
+    end
+
+    it 'with semver operators and v-prefix' do
+      property = { 'key' => 'version', 'value' => '1.2.3', 'operator' => 'semver_eq' }
+      expect(FeatureFlagsPoller.match_property(property, { 'version' => 'v1.2.3' })).to be true
+      expect(FeatureFlagsPoller.match_property(property, { 'version' => 'V1.2.3' })).to be true
+
+      property2 = { 'key' => 'version', 'value' => 'v1.2.3', 'operator' => 'semver_eq' }
+      expect(FeatureFlagsPoller.match_property(property2, { 'version' => '1.2.3' })).to be true
+      expect(FeatureFlagsPoller.match_property(property2, { 'version' => 'v1.2.3' })).to be true
+    end
+
+    it 'with semver operators and pre-release suffixes stripped' do
+      property = { 'key' => 'version', 'value' => '1.2.3', 'operator' => 'semver_eq' }
+      expect(FeatureFlagsPoller.match_property(property, { 'version' => '1.2.3-alpha' })).to be true
+      expect(FeatureFlagsPoller.match_property(property, { 'version' => '1.2.3-beta.1' })).to be true
+      expect(FeatureFlagsPoller.match_property(property, { 'version' => '1.2.3+build' })).to be true
+      expect(FeatureFlagsPoller.match_property(property, { 'version' => '1.2.3-alpha+build' })).to be true
+
+      property2 = { 'key' => 'version', 'value' => '1.2.3-alpha', 'operator' => 'semver_eq' }
+      expect(FeatureFlagsPoller.match_property(property2, { 'version' => '1.2.3' })).to be true
+    end
+
+    it 'with semver operators and whitespace handling' do
+      property = { 'key' => 'version', 'value' => '1.2.3', 'operator' => 'semver_eq' }
+      expect(FeatureFlagsPoller.match_property(property, { 'version' => ' 1.2.3 ' })).to be true
+      expect(FeatureFlagsPoller.match_property(property, { 'version' => '  1.2.3' })).to be true
+
+      property2 = { 'key' => 'version', 'value' => ' 1.2.3 ', 'operator' => 'semver_eq' }
+      expect(FeatureFlagsPoller.match_property(property2, { 'version' => '1.2.3' })).to be true
+    end
+
+    it 'with semver operators and leading zeros' do
+      property = { 'key' => 'version', 'value' => '1.2.3', 'operator' => 'semver_eq' }
+      expect(FeatureFlagsPoller.match_property(property, { 'version' => '01.02.03' })).to be true
+      expect(FeatureFlagsPoller.match_property(property, { 'version' => '001.002.003' })).to be true
+    end
+
+    it 'with semver operators and partial versions' do
+      # "1.2" equals "1.2.0"
+      property = { 'key' => 'version', 'value' => '1.2.0', 'operator' => 'semver_eq' }
+      expect(FeatureFlagsPoller.match_property(property, { 'version' => '1.2' })).to be true
+
+      property2 = { 'key' => 'version', 'value' => '1.2', 'operator' => 'semver_eq' }
+      expect(FeatureFlagsPoller.match_property(property2, { 'version' => '1.2.0' })).to be true
+
+      # "1" equals "1.0.0"
+      property3 = { 'key' => 'version', 'value' => '1.0.0', 'operator' => 'semver_eq' }
+      expect(FeatureFlagsPoller.match_property(property3, { 'version' => '1' })).to be true
+
+      property4 = { 'key' => 'version', 'value' => '1', 'operator' => 'semver_eq' }
+      expect(FeatureFlagsPoller.match_property(property4, { 'version' => '1.0.0' })).to be true
+    end
+
+    it 'with semver operators and 4-part versions' do
+      # "1.2.3.4" equals "1.2.3" (extra parts ignored)
+      property = { 'key' => 'version', 'value' => '1.2.3', 'operator' => 'semver_eq' }
+      expect(FeatureFlagsPoller.match_property(property, { 'version' => '1.2.3.4' })).to be true
+      expect(FeatureFlagsPoller.match_property(property, { 'version' => '1.2.3.999' })).to be true
+
+      property2 = { 'key' => 'version', 'value' => '1.2.3.4', 'operator' => 'semver_eq' }
+      expect(FeatureFlagsPoller.match_property(property2, { 'version' => '1.2.3' })).to be true
+    end
+
+    it 'with semver operators and invalid values' do
+      property = { 'key' => 'version', 'value' => '1.2.3', 'operator' => 'semver_eq' }
+
+      # Non-numeric strings raise InconclusiveMatchError
+      expect do
+        FeatureFlagsPoller.match_property(property, { 'version' => 'not-a-version' })
+      end.to raise_error(InconclusiveMatchError)
+
+      expect do
+        FeatureFlagsPoller.match_property(property, { 'version' => '' })
+      end.to raise_error(InconclusiveMatchError)
+
+      expect do
+        FeatureFlagsPoller.match_property(property, { 'version' => '.1.2.3' })
+      end.to raise_error(InconclusiveMatchError)
+
+      expect do
+        FeatureFlagsPoller.match_property(property, { 'version' => 'abc.def.ghi' })
+      end.to raise_error(InconclusiveMatchError)
+
+      # Invalid flag condition value
+      invalid_property = { 'key' => 'version', 'value' => 'invalid', 'operator' => 'semver_eq' }
+      expect do
+        FeatureFlagsPoller.match_property(invalid_property, { 'version' => '1.2.3' })
+      end.to raise_error(InconclusiveMatchError)
+    end
+
+    it 'with semver operators and missing property key' do
+      property = { 'key' => 'version', 'value' => '1.2.3', 'operator' => 'semver_eq' }
+      expect do
+        FeatureFlagsPoller.match_property(property, { 'other_key' => '1.2.3' })
+      end.to raise_error(InconclusiveMatchError)
+
+      expect do
+        FeatureFlagsPoller.match_property(property, {})
+      end.to raise_error(InconclusiveMatchError)
+    end
+
+    it 'with semver operators and null property value' do
+      property = { 'key' => 'version', 'value' => '1.2.3', 'operator' => 'semver_eq' }
+      expect do
+        FeatureFlagsPoller.match_property(property, { 'version' => nil })
+      end.to raise_error(InconclusiveMatchError)
+    end
+
+    it 'with semver_wildcard invalid patterns' do
+      # Invalid wildcard pattern - completely empty after cleaning
+      property = { 'key' => 'version', 'value' => '*', 'operator' => 'semver_wildcard' }
+      expect do
+        FeatureFlagsPoller.match_property(property, { 'version' => '1.2.3' })
+      end.to raise_error(InconclusiveMatchError)
+
+      property2 = { 'key' => 'version', 'value' => '*.*', 'operator' => 'semver_wildcard' }
+      expect do
+        FeatureFlagsPoller.match_property(property2, { 'version' => '1.2.3' })
+      end.to raise_error(InconclusiveMatchError)
+    end
   end
 
   describe 'relative date parsing' do