diff --git a/airbyte-workers/src/main/java/io/airbyte/workers/temporal/TemporalClient.java b/airbyte-workers/src/main/java/io/airbyte/workers/temporal/TemporalClient.java
index c843954f4a23..a0d6a0c57e5e 100644
--- a/airbyte-workers/src/main/java/io/airbyte/workers/temporal/TemporalClient.java
+++ b/airbyte-workers/src/main/java/io/airbyte/workers/temporal/TemporalClient.java
@@ -252,9 +252,32 @@ public void submitConnectionUpdaterAsync(final UUID connectionId) {
   }
 
   public void deleteConnection(final UUID connectionId) {
-    final ConnectionManagerWorkflow connectionManagerWorkflow = getConnectionUpdateWorkflow(connectionId);
-
-    connectionManagerWorkflow.deleteConnection();
+    try {
+      final ConnectionManagerWorkflow connectionManagerWorkflow = getConnectionUpdateWorkflow(connectionId);
+      connectionManagerWorkflow.deleteConnection();
+    } catch (final IllegalStateException e) {
+      log.info("Connection in an illegal state; Creating new workflow and sending delete signal");
+
+      final ConnectionManagerWorkflow connectionManagerWorkflow = getWorkflowOptionsWithWorkflowId(ConnectionManagerWorkflow.class,
+          TemporalJobType.CONNECTION_UPDATER, getConnectionManagerName(connectionId));
+
+      final ConnectionUpdaterInput input = ConnectionUpdaterInput.builder()
+          .connectionId(connectionId)
+          .jobId(null)
+          .attemptId(null)
+          .fromFailure(false)
+          .attemptNumber(1)
+          .workflowState(null)
+          .resetConnection(false)
+          .fromJobResetFailure(false)
+          .build();
+
+      final BatchRequest signalRequest = client.newSignalWithStartRequest();
+      signalRequest.add(connectionManagerWorkflow::run, input);
+      signalRequest.add(connectionManagerWorkflow::deleteConnection);
+      client.signalWithStart(signalRequest);
+      log.info("New start request and delete signal submitted");
+    }
   }
 
   public void update(final UUID connectionId) {
@@ -444,7 +467,7 @@ private <T> T getExistingWorkflow(final Class<T> workflowClass, final String nam
     return client.newWorkflowStub(workflowClass, name);
   }
 
-  private ConnectionManagerWorkflow getConnectionUpdateWorkflow(final UUID connectionId) {
+  ConnectionManagerWorkflow getConnectionUpdateWorkflow(final UUID connectionId) {
     final boolean workflowReachable = isWorkflowReachable(getConnectionManagerName(connectionId));
 
     if (!workflowReachable) {
@@ -505,7 +528,6 @@ boolean isWorkflowStateRunning(final String workflowName) {
     }
   }
 
-  @VisibleForTesting
   static String getConnectionManagerName(final UUID connectionId) {
     return "connection_manager_" + connectionId;
   }
diff --git a/airbyte-workers/src/test/java/io/airbyte/workers/temporal/TemporalClientTest.java b/airbyte-workers/src/test/java/io/airbyte/workers/temporal/TemporalClientTest.java
index fa9c9e7e3763..d64fe77d965b 100644
--- a/airbyte-workers/src/test/java/io/airbyte/workers/temporal/TemporalClientTest.java
+++ b/airbyte-workers/src/test/java/io/airbyte/workers/temporal/TemporalClientTest.java
@@ -12,6 +12,7 @@
 import static org.mockito.ArgumentMatchers.anyString;
 import static org.mockito.Mockito.doNothing;
 import static org.mockito.Mockito.doReturn;
+import static org.mockito.Mockito.doThrow;
 import static org.mockito.Mockito.mock;
 import static org.mockito.Mockito.spy;
 import static org.mockito.Mockito.times;
@@ -39,7 +40,9 @@
 import io.airbyte.workers.temporal.scheduling.ConnectionManagerWorkflow.JobInformation;
 import io.airbyte.workers.temporal.spec.SpecWorkflow;
 import io.airbyte.workers.temporal.sync.SyncWorkflow;
+import io.temporal.client.BatchRequest;
 import io.temporal.client.WorkflowClient;
+import io.temporal.client.WorkflowOptions;
 import io.temporal.serviceclient.WorkflowServiceStubs;
 import java.io.IOException;
 import java.nio.file.Files;
@@ -51,6 +54,7 @@
 import org.junit.jupiter.api.DisplayName;
 import org.junit.jupiter.api.Nested;
 import org.junit.jupiter.api.Test;
+import org.mockito.Mockito;
 
 class TemporalClientTest {
 
@@ -257,4 +261,54 @@ public void migrateCalled() {
 
   }
 
+  @Nested
+  @DisplayName("Test delete connection method.")
+  class DeleteConnection {
+
+    @Test
+    @SuppressWarnings("unchecked")
+    @DisplayName("Test delete connection method.")
+    void testDeleteConnection() {
+      final ConnectionManagerWorkflow mConnectionManagerWorkflow = mock(ConnectionManagerWorkflow.class);
+
+      doReturn(true).when(temporalClient).isWorkflowReachable(anyString());
+      when(workflowClient.newWorkflowStub(any(Class.class), anyString())).thenReturn(mConnectionManagerWorkflow);
+
+      final JobSyncConfig syncConfig = new JobSyncConfig()
+          .withSourceDockerImage(IMAGE_NAME1)
+          .withSourceDockerImage(IMAGE_NAME2)
+          .withSourceConfiguration(Jsons.emptyObject())
+          .withDestinationConfiguration(Jsons.emptyObject())
+          .withOperationSequence(List.of())
+          .withConfiguredAirbyteCatalog(new ConfiguredAirbyteCatalog());
+
+      temporalClient.submitSync(JOB_ID, ATTEMPT_ID, syncConfig, CONNECTION_ID);
+      temporalClient.deleteConnection(CONNECTION_ID);
+
+      verify(workflowClient, Mockito.never()).newSignalWithStartRequest();
+      verify(mConnectionManagerWorkflow).deleteConnection();
+    }
+
+    @Test
+    @SuppressWarnings("unchecked")
+    @DisplayName("Test delete connection method when workflow is in an unexpected state")
+    void testDeleteConnectionInUnexpectedState() {
+      final ConnectionManagerWorkflow mConnectionManagerWorkflow = mock(ConnectionManagerWorkflow.class);
+      final BatchRequest mBatchRequest = mock(BatchRequest.class);
+
+      doThrow(new IllegalStateException("Force illegal state")).when(temporalClient).getConnectionUpdateWorkflow(CONNECTION_ID);
+      when(workflowClient.newWorkflowStub(any(Class.class), any(WorkflowOptions.class))).thenReturn(mConnectionManagerWorkflow);
+      when(workflowClient.newSignalWithStartRequest()).thenReturn(mBatchRequest);
+
+      temporalClient.deleteConnection(CONNECTION_ID);
+
+      // this is only called when getting existing workflow
+      verify(workflowClient, Mockito.never()).newWorkflowStub(any(), anyString());
+
+      verify(workflowClient).newSignalWithStartRequest();
+      verify(workflowClient).signalWithStart(mBatchRequest);
+    }
+
+  }
+
 }