diff --git a/.changeset/relative-date-month-clamp.md b/.changeset/relative-date-month-clamp.md
new file mode 100644
index 00000000..1b7b4435
--- /dev/null
+++ b/.changeset/relative-date-month-clamp.md
@@ -0,0 +1,5 @@
+---
+"posthog-ruby": patch
+---
+
+Relative date filters in local flag evaluation now clamp the day after every month or year step, as the SDK spec requires. `2m` on March 31 resolves to January 28 instead of January 31, and `4y` on February 29, 2024 to February 28, 2020.
diff --git a/lib/posthog/feature_flags.rb b/lib/posthog/feature_flags.rb
index 9f57d23c..64b2cc2e 100644
--- a/lib/posthog/feature_flags.rb
+++ b/lib/posthog/feature_flags.rb
@@ -548,9 +548,9 @@ def self.relative_date_parse_for_feature_flag_matching(value)
       when 'w'
         parsed_dt = parsed_dt.prev_day(number * 7)
       when 'm'
-        parsed_dt = parsed_dt.prev_month(number)
+        parsed_dt = subtract_months(parsed_dt, number)
       when 'y'
-        parsed_dt = parsed_dt.prev_year(number)
+        parsed_dt = subtract_years(parsed_dt, number)
       else
         return nil
       end
@@ -558,6 +558,30 @@ def self.relative_date_parse_for_feature_flag_matching(value)
       parsed_dt
     end
 
+    # Steps back one month at a time and clamps the day after every step, as the
+    # SDK spec requires: March 31 minus two months is January 28. A single
+    # prev_month(2) clamps once and lands on January 31.
+    def self.subtract_months(date_time, months)
+      steps = 0
+      # Every month has at least 28 days, so once the day is 28 or less no step
+      # can clamp it again and the rest can be done in one jump.
+      while steps < months && date_time.day > 28
+        date_time = date_time.prev_month
+        steps += 1
+      end
+      date_time.prev_month(months - steps)
+    end
+    private_class_method :subtract_months
+
+    # Years work the same way. Only February 29 can clamp, and only on the first
+    # step, so one step followed by a single jump matches stepping every year.
+    def self.subtract_years(date_time, years)
+      return date_time if years.zero?
+
+      date_time.prev_year.prev_year(years - 1)
+    end
+    private_class_method :subtract_years
+
     # Parse a single semver numeric identifier, rejecting empty, non-digit, or
     # leading-zero values per semver 2.0.0 §2. `reason` names the owner of the value:
     # UNSUPPORTED_DEFINITION for a filter value, MISSING_CONTEXT for a value the call passed.
diff --git a/spec/posthog/feature_flag_spec.rb b/spec/posthog/feature_flag_spec.rb
index e0fdb047..a9b5986e 100644
--- a/spec/posthog/feature_flag_spec.rb
+++ b/spec/posthog/feature_flag_spec.rb
@@ -2537,6 +2537,29 @@ module PostHog
       end
     end
 
+    it 'clamps month and year lookbacks after every step' do
+      [
+        [[2025, 3, 31], '1m', [2025, 2, 28]],
+        [[2025, 5, 31], '1m', [2025, 4, 30]],
+        [[2024, 3, 31], '1m', [2024, 2, 29]],
+        [[2025, 3, 31], '2m', [2025, 1, 28]],
+        [[2025, 3, 31], '13m', [2024, 2, 28]],
+        [[2025, 12, 31], '10m', [2025, 2, 28]],
+        [[2019, 1, 29], '12m', [2018, 1, 28]],
+        [[2019, 1, 29], '1y', [2018, 1, 29]],
+        [[2025, 3, 31], '0m', [2025, 3, 31]],
+        [[2024, 2, 29], '1y', [2023, 2, 28]],
+        [[2024, 2, 29], '4y', [2020, 2, 28]],
+        [[2024, 2, 29], '0y', [2024, 2, 29]]
+      ].each do |now, value, expected|
+        Timecop.freeze(Time.gm(*now, 12, 0, 0)) do
+          expect(
+            FeatureFlagsPoller.relative_date_parse_for_feature_flag_matching(value)
+          ).to eq(DateTime.new(*expected, 12, 0, 0, Rational(0, 24))), "#{value} from #{now.join('-')}"
+        end
+      end
+    end
+
     it 'test year parsing' do
       Timecop.freeze(Time.gm(2020, 1, 1, 12, 1, 20, 134_000, 0)) do
         expect(