diff --git a/src/main/java/com/zaxxer/hikari/pool/HikariPool.java b/src/main/java/com/zaxxer/hikari/pool/HikariPool.java
index a7b21ec47..968df12a5 100644
--- a/src/main/java/com/zaxxer/hikari/pool/HikariPool.java
+++ b/src/main/java/com/zaxxer/hikari/pool/HikariPool.java
@@ -705,14 +705,18 @@ private SQLException createTimeoutException(long startTime)
       String sqlState = null;
       int errorCode = 0;
       final var originalException = getLastConnectionFailure();
+      Long lastConnectionFailureTimestamp = getLastConnectionFailureTimestamp();
       if (originalException instanceof SQLException) {
          sqlState = ((SQLException) originalException).getSQLState();
          errorCode = ((SQLException) originalException).getErrorCode();
       }
-      final var connectionException = new SQLTransientConnectionException(
-         poolName + " - Connection is not available, request timed out after " + elapsedMillis(startTime) + "ms " +
-            "(total=" + getTotalConnections() + ", active=" + getActiveConnections() + ", idle=" + getIdleConnections() + ", waiting=" + getThreadsAwaitingConnection() + ")",
-         sqlState, errorCode, originalException);
+      String errorDescription = poolName + " - Connection is not available, request timed out after " + elapsedMillis(startTime) + "ms " +
+         "(total=" + getTotalConnections() + ", active=" + getActiveConnections() + ", idle=" + getIdleConnections() + ", waiting=" + getThreadsAwaitingConnection() + ")";
+      if (lastConnectionFailureTimestamp != null && lastConnectionFailureTimestamp != 0) {
+         errorDescription += " - The last connection failure (appended as the next exception below) happened " +
+            elapsedDisplayString(lastConnectionFailureTimestamp, currentTime()) + " ago.";
+      }
+      final var connectionException = new SQLTransientConnectionException(errorDescription, sqlState, errorCode, originalException);
       if (originalException instanceof SQLException) {
          connectionException.setNextException((SQLException) originalException);
       }
diff --git a/src/main/java/com/zaxxer/hikari/pool/PoolBase.java b/src/main/java/com/zaxxer/hikari/pool/PoolBase.java
index 803f4bbbd..bc49cd1af 100644
--- a/src/main/java/com/zaxxer/hikari/pool/PoolBase.java
+++ b/src/main/java/com/zaxxer/hikari/pool/PoolBase.java
@@ -62,6 +62,7 @@ abstract class PoolBase
 
    volatile String catalog;
    final AtomicReference<Throwable> lastConnectionFailure;
+   final AtomicLong lastConnectionFailureTimestamp;
    final AtomicLong connectionFailureTimestamp;
 
    long connectionTimeout;
@@ -116,6 +117,7 @@ abstract class PoolBase
       this.connectionTimeout = config.getConnectionTimeout();
       this.validationTimeout = config.getValidationTimeout();
       this.lastConnectionFailure = new AtomicReference<>();
+      this.lastConnectionFailureTimestamp = new AtomicLong();
       this.connectionFailureTimestamp = new AtomicLong();
 
       initializeDataSource();
@@ -185,6 +187,7 @@ boolean isConnectionDead(final Connection connection)
       }
       catch (Exception e) {
          lastConnectionFailure.set(e);
+         lastConnectionFailureTimestamp.set(currentTime());
          logger.warn("{} - Failed to validate connection {} ({}). Possibly consider using a shorter maxLifetime value.",
                      poolName, connection, e.getMessage());
          return true;
@@ -196,6 +199,10 @@ Throwable getLastConnectionFailure()
       return lastConnectionFailure.get();
    }
 
+   Long getLastConnectionFailureTimestamp(){
+      return lastConnectionFailureTimestamp.get();
+   }
+
    public DataSource getUnwrappedDataSource()
    {
       return dataSource;
@@ -378,6 +385,7 @@ private Connection newConnection(final boolean isEmptyPool) throws Exception
          setupConnection(connection);
 
          lastConnectionFailure.set(null);
+         lastConnectionFailureTimestamp.set(0);
          connectionFailureTimestamp.set(0);
 
          logger.debug("{} - Established new connection ({})", poolName, id);
@@ -397,6 +405,7 @@ private Connection newConnection(final boolean isEmptyPool) throws Exception
          }
 
          lastConnectionFailure.set(t);
+         lastConnectionFailureTimestamp.set(currentTime());
          throw t;
       }
       finally {