diff --git a/libs/posthog_client_lite/src/lib.rs b/libs/posthog_client_lite/src/lib.rs
index ff12051196..281a8f8011 100644
--- a/libs/posthog_client_lite/src/lib.rs
+++ b/libs/posthog_client_lite/src/lib.rs
@@ -22,6 +22,16 @@ pub enum PostHogEvaluationError {
     Internal(String),
 }
 
+impl PostHogEvaluationError {
+    pub fn as_variant_str(&self) -> &'static str {
+        match self {
+            PostHogEvaluationError::NotAvailable(_) => "not_available",
+            PostHogEvaluationError::NoConditionGroupMatched => "no_condition_group_matched",
+            PostHogEvaluationError::Internal(_) => "internal",
+        }
+    }
+}
+
 #[derive(Deserialize)]
 pub struct LocalEvaluationResponse {
     pub flags: Vec<LocalEvaluationFlag>,
diff --git a/pageserver/src/feature_resolver.rs b/pageserver/src/feature_resolver.rs
index 7e31b930d0..7463186c06 100644
--- a/pageserver/src/feature_resolver.rs
+++ b/pageserver/src/feature_resolver.rs
@@ -6,7 +6,7 @@ use posthog_client_lite::{
 use tokio_util::sync::CancellationToken;
 use utils::id::TenantId;
 
-use crate::config::PageServerConf;
+use crate::{config::PageServerConf, metrics::FEATURE_FLAG_EVALUATION};
 
 #[derive(Clone)]
 pub struct FeatureResolver {
@@ -55,11 +55,24 @@ impl FeatureResolver {
         tenant_id: TenantId,
     ) -> Result<String, PostHogEvaluationError> {
         if let Some(inner) = &self.inner {
-            inner.feature_store().evaluate_multivariate(
+            let res = inner.feature_store().evaluate_multivariate(
                 flag_key,
                 &tenant_id.to_string(),
                 &HashMap::new(),
-            )
+            );
+            match &res {
+                Ok(value) => {
+                    FEATURE_FLAG_EVALUATION
+                        .with_label_values(&[flag_key, "ok", value])
+                        .inc();
+                }
+                Err(e) => {
+                    FEATURE_FLAG_EVALUATION
+                        .with_label_values(&[flag_key, "error", e.as_variant_str()])
+                        .inc();
+                }
+            }
+            res
         } else {
             Err(PostHogEvaluationError::NotAvailable(
                 "PostHog integration is not enabled".to_string(),
@@ -80,11 +93,24 @@ impl FeatureResolver {
         tenant_id: TenantId,
     ) -> Result<(), PostHogEvaluationError> {
         if let Some(inner) = &self.inner {
-            inner.feature_store().evaluate_boolean(
+            let res = inner.feature_store().evaluate_boolean(
                 flag_key,
                 &tenant_id.to_string(),
                 &HashMap::new(),
-            )
+            );
+            match &res {
+                Ok(()) => {
+                    FEATURE_FLAG_EVALUATION
+                        .with_label_values(&[flag_key, "ok", "true"])
+                        .inc();
+                }
+                Err(e) => {
+                    FEATURE_FLAG_EVALUATION
+                        .with_label_values(&[flag_key, "error", e.as_variant_str()])
+                        .inc();
+                }
+            }
+            res
         } else {
             Err(PostHogEvaluationError::NotAvailable(
                 "PostHog integration is not enabled".to_string(),
diff --git a/pageserver/src/metrics.rs b/pageserver/src/metrics.rs
index 4bef9b44a7..3173ab221f 100644
--- a/pageserver/src/metrics.rs
+++ b/pageserver/src/metrics.rs
@@ -446,6 +446,15 @@ static PAGE_CACHE_ERRORS: Lazy<IntCounterVec> = Lazy::new(|| {
     .expect("failed to define a metric")
 });
 
+pub(crate) static FEATURE_FLAG_EVALUATION: Lazy<CounterVec> = Lazy::new(|| {
+    register_counter_vec!(
+        "pageserver_feature_flag_evaluation",
+        "Number of times a feature flag is evaluated",
+        &["flag_key", "status", "value"],
+    )
+    .unwrap()
+});
+
 #[derive(IntoStaticStr)]
 #[strum(serialize_all = "kebab_case")]
 pub(crate) enum PageCacheErrorKind {