diff --git a/core/src/api.rs b/core/src/api.rs
index eb4b5d03..7533b7c2 100644
--- a/core/src/api.rs
+++ b/core/src/api.rs
@@ -375,6 +375,10 @@ where
 /// credential providers together. The chain will try each provider in order until one
 /// returns credentials or all providers have been exhausted.
 ///
+/// A provider error does not stop the chain. If no provider returns credentials and
+/// at least one provider failed with a retryable error, the first such error is
+/// returned so that the caller can retry it. Otherwise the chain returns `Ok(None)`.
+///
 /// # Example
 ///
 /// ```no_run
@@ -479,6 +483,8 @@ where
     type Credential = C;
 
     async fn provide_credential(&self, ctx: &Context) -> Result<Option<Self::Credential>> {
+        let mut retryable_error = None;
+
         for provider in &self.providers {
             log::debug!("Trying credential provider: {provider:?}");
 
@@ -493,19 +499,26 @@ where
                 }
                 Err(e) => {
                     log::warn!("Error loading credential from provider {provider:?}: {e:?}");
+                    if e.is_retryable() && retryable_error.is_none() {
+                        retryable_error = Some(e);
+                    }
                     // Continue to next provider on error
                     continue;
                 }
             }
         }
 
-        Ok(None)
+        match retryable_error {
+            Some(err) => Err(err),
+            None => Ok(None),
+        }
     }
 }
 
 #[cfg(test)]
 mod tests {
     use super::*;
+    use crate::Error;
 
     #[derive(Clone, Debug)]
     struct ExactCredential {
@@ -533,4 +546,56 @@ mod tests {
         assert!(!credential.is_valid_at(timestamp + Duration::from_secs(1)));
         assert!(!None::<ExactCredential>.is_valid_at(timestamp));
     }
+
+    #[derive(Debug)]
+    struct FixedProvider(fn() -> Result<Option<&'static str>>);
+
+    impl ProvideCredential for FixedProvider {
+        type Credential = &'static str;
+
+        async fn provide_credential(&self, _ctx: &Context) -> Result<Option<Self::Credential>> {
+            (self.0)()
+        }
+    }
+
+    fn chain_result(chain: ProvideCredentialChain<&'static str>) -> Result<Option<&'static str>> {
+        futures::executor::block_on(chain.provide_credential(&Context::new()))
+    }
+
+    #[test]
+    fn chain_returns_later_credential_after_retryable_error() {
+        let chain = ProvideCredentialChain::new()
+            .push(FixedProvider(|| {
+                Err(Error::unexpected("transient").set_retryable(true))
+            }))
+            .push(FixedProvider(|| Ok(Some("credential"))));
+
+        assert_eq!(chain_result(chain).unwrap(), Some("credential"));
+    }
+
+    #[test]
+    fn chain_returns_first_retryable_error_when_no_credential_found() {
+        let chain = ProvideCredentialChain::new()
+            .push(FixedProvider(|| Err(Error::config_invalid("persistent"))))
+            .push(FixedProvider(|| {
+                Err(Error::unexpected("first transient").set_retryable(true))
+            }))
+            .push(FixedProvider(|| Ok(None)))
+            .push(FixedProvider(|| {
+                Err(Error::unexpected("second transient").set_retryable(true))
+            }));
+
+        let err = chain_result(chain).expect_err("retryable error must be returned");
+        assert_eq!(err.to_string(), "first transient");
+        assert!(err.is_retryable());
+    }
+
+    #[test]
+    fn chain_skips_persistent_errors_when_no_credential_found() {
+        let chain = ProvideCredentialChain::new()
+            .push(FixedProvider(|| Err(Error::config_invalid("persistent"))))
+            .push(FixedProvider(|| Ok(None)));
+
+        assert_eq!(chain_result(chain).unwrap(), None);
+    }
 }
diff --git a/core/src/signer.rs b/core/src/signer.rs
index 168bf9f9..9ec86e05 100644
--- a/core/src/signer.rs
+++ b/core/src/signer.rs
@@ -180,7 +180,7 @@ impl<K: SigningCredential> Signer<K> {
 mod tests {
     use super::*;
     use crate::time::Timestamp;
-    use crate::{ErrorKind, ProvideCredential, SignRequest};
+    use crate::{ErrorKind, ProvideCredential, ProvideCredentialChain, SignRequest};
     use asyncband::oneshot;
     use futures::future::{join_all, pending};
     use futures::poll;
@@ -1030,6 +1030,60 @@ mod tests {
         );
     }
 
+    #[test]
+    fn chained_retryable_provider_error_reaches_caller() {
+        let base = Timestamp::from_second(3_500).expect("timestamp must be valid");
+        let refreshed = ExpiringCredential {
+            generation: 2,
+            fresh: true,
+            expires_at: base + Duration::from_secs(30),
+            required_until: base + Duration::from_secs(10),
+        };
+        let (provider, calls) = SequenceProvider::new([
+            Err(Error::unexpected("injected transient failure").set_retryable(true)),
+            Ok(Some(refreshed)),
+        ]);
+        let signer = Signer::new(
+            Context::new(),
+            ProvideCredentialChain::new().push(provider),
+            OperationSigner,
+        );
+
+        let mut parts = request_parts();
+        let err = futures::executor::block_on(signer.sign(&mut parts, None))
+            .expect_err("retryable provider error must be returned");
+        assert_eq!(err.kind(), ErrorKind::Unexpected);
+        assert_eq!(err.to_string(), "injected transient failure");
+        assert!(err.is_retryable());
+        assert_eq!(calls.load(Ordering::SeqCst), 1);
+
+        futures::executor::block_on(signer.sign(&mut parts, None))
+            .expect("caller retry must load the credential");
+        assert_eq!(calls.load(Ordering::SeqCst), 2);
+        assert_eq!(
+            parts.headers.get("x-credential-generation"),
+            Some(&HeaderValue::from_static("2"))
+        );
+    }
+
+    #[test]
+    fn chained_persistent_provider_error_stays_persistent() {
+        let (provider, calls) =
+            SequenceProvider::new([Err(Error::unexpected("injected persistent failure"))]);
+        let signer = Signer::new(
+            Context::new(),
+            ProvideCredentialChain::new().push(provider),
+            OperationSigner,
+        );
+
+        let mut parts = request_parts();
+        let err = futures::executor::block_on(signer.sign(&mut parts, None))
+            .expect_err("missing credential must be returned");
+        assert_eq!(err.kind(), ErrorKind::CredentialInvalid);
+        assert!(!err.is_retryable());
+        assert_eq!(calls.load(Ordering::SeqCst), 1);
+    }
+
     #[test]
     fn missing_refresh_does_not_fall_back_and_caller_can_retry() {
         let base = Timestamp::from_second(4_000).expect("timestamp must be valid");