diff --git a/src/main/java/com/microsoft/sqlserver/jdbc/SQLServerConnection.java b/src/main/java/com/microsoft/sqlserver/jdbc/SQLServerConnection.java
index 79b7223eb..980839562 100644
--- a/src/main/java/com/microsoft/sqlserver/jdbc/SQLServerConnection.java
+++ b/src/main/java/com/microsoft/sqlserver/jdbc/SQLServerConnection.java
@@ -2195,6 +2195,11 @@ Connection connect(Properties propsIn, SQLServerPooledConnection pooledConnectio
 
         long elapsedSeconds = 0;
         long start = System.currentTimeMillis();
+
+        // Any existing enclave session would be invalid, make sure it is invalidated.
+        // For example, if this is a session recovery reconnect.
+        //
+        invalidateEnclaveSessionCache();
         for (int connectRetryAttempt = 0, tlsRetryAttempt = 0;;) {
             try {
                 if (0 == elapsedSeconds || elapsedSeconds < loginTimeoutSeconds) {
@@ -8969,6 +8974,15 @@ ArrayList<byte[]> initEnclaveParameters(SQLServerStatement statement, String use
                 parameterNames);
     }
 
+    void invalidateEnclaveSessionCache() {
+        if (enclaveProvider != null) {
+            if (connectionlogger.isLoggable(Level.FINE)) {
+                connectionlogger.fine("Invalidating existing enclave session for enclave provider : " + enclaveProvider);
+            }
+            enclaveProvider.invalidateEnclaveSession();
+        }
+    }
+
     boolean enclaveEstablished() {
         return (null != enclaveProvider.getEnclaveSession());
     }
diff --git a/src/main/java/com/microsoft/sqlserver/jdbc/SQLServerException.java b/src/main/java/com/microsoft/sqlserver/jdbc/SQLServerException.java
index ba35b84a2..7f057eca4 100644
--- a/src/main/java/com/microsoft/sqlserver/jdbc/SQLServerException.java
+++ b/src/main/java/com/microsoft/sqlserver/jdbc/SQLServerException.java
@@ -73,6 +73,8 @@ public final class SQLServerException extends java.sql.SQLException {
     // Built-in function '%.*ls' in impersonation context is not supported in this version of SQL Server.
     static final int IMPERSONATION_CONTEXT_NOT_SUPPORTED = 40529;
 
+    static final int INVAID_ENCLAVE_SESSION_HANDLE_ERROR = 33195;
+
     // Facility for driver-specific error codes
     static final int DRIVER_ERROR_NONE = 0;
     static final int DRIVER_ERROR_FROM_DATABASE = 2;
diff --git a/src/main/java/com/microsoft/sqlserver/jdbc/SQLServerPreparedStatement.java b/src/main/java/com/microsoft/sqlserver/jdbc/SQLServerPreparedStatement.java
index 2a0c79d97..36fc3e73e 100644
--- a/src/main/java/com/microsoft/sqlserver/jdbc/SQLServerPreparedStatement.java
+++ b/src/main/java/com/microsoft/sqlserver/jdbc/SQLServerPreparedStatement.java
@@ -687,6 +687,12 @@ final void doExecutePreparedStatement(PrepStmtExecCmd command) throws SQLServerE
                 startResults();
                 getNextResult(true);
             } catch (SQLException e) {
+                if (connection.isAEv2() && (e.getErrorCode() == SQLServerException.INVAID_ENCLAVE_SESSION_HANDLE_ERROR)) {
+                    //If the exception received is as below then just invalidate the cache 
+                    //code = '33195', SQL state = 'S0001': Internal enclave error. Enclave was provided with an invalid session handle. For more information, contact Customer Support Services..
+                    //
+                    connection.invalidateEnclaveSessionCache();
+                }
                 if (retryBasedOnFailedReuseOfCachedHandle(e, attempt, needsPrepare, false)) {
                     continue;
                 } else if (!inRetry && connection.doesServerSupportEnclaveRetry()) {
@@ -3119,6 +3125,12 @@ final void doExecutePreparedStatementBatch(PrepStmtBatchExecCmd batchCommand) th
                         assert numBatchesExecuted == numBatchesPrepared;
                     }
                 } catch (SQLException e) {
+                    if (connection.isAEv2() && (e.getErrorCode() == SQLServerException.INVAID_ENCLAVE_SESSION_HANDLE_ERROR)) {
+                        //If the exception received is as below then just invalidate the cache 
+                        //code = '33195', SQL state = 'S0001': Internal enclave error. Enclave was provided with an invalid session handle. For more information, contact Customer Support Services..
+                        //
+                        connection.invalidateEnclaveSessionCache();
+                    }
                     if (retryBasedOnFailedReuseOfCachedHandle(e, attempt, needsPrepare, true)
                             && connection.isStatementPoolingEnabled()) {
                         // Reset number of batches prepared.