diff --git a/nifi-nar-bundles/nifi-framework-bundle/nifi-framework/nifi-framework-components/src/main/java/org/apache/nifi/controller/StandardProcessorNode.java b/nifi-nar-bundles/nifi-framework-bundle/nifi-framework/nifi-framework-components/src/main/java/org/apache/nifi/controller/StandardProcessorNode.java
index c7dd22d6f4..e740336a6d 100644
--- a/nifi-nar-bundles/nifi-framework-bundle/nifi-framework/nifi-framework-components/src/main/java/org/apache/nifi/controller/StandardProcessorNode.java
+++ b/nifi-nar-bundles/nifi-framework-bundle/nifi-framework/nifi-framework-components/src/main/java/org/apache/nifi/controller/StandardProcessorNode.java
@@ -1594,7 +1594,7 @@ public class StandardProcessorNode extends ProcessorNode implements Connectable
         }
 
         if (starting) { // will ensure that the Processor represented by this node can only be started once
-            initiateStart(taskScheduler, administrativeYieldMillis, timeoutMillis, processContextFactory, schedulingAgentCallback);
+            initiateStart(taskScheduler, administrativeYieldMillis, timeoutMillis, new AtomicLong(0), processContextFactory, schedulingAgentCallback);
         } else {
             final String procName = processorRef.get().getProcessor().toString();
             procLog.warn("Cannot start {} because it is not currently stopped. Current state is {}", procName, currentState);
@@ -1711,7 +1711,7 @@ public class StandardProcessorNode extends ProcessorNode implements Connectable
 
 
     private void initiateStart(final ScheduledExecutorService taskScheduler, final long administrativeYieldMillis, final long timeoutMilis,
-            final Supplier<ProcessContext> processContextFactory, final SchedulingAgentCallback schedulingAgentCallback) {
+            AtomicLong startupAttemptCount, final Supplier<ProcessContext> processContextFactory, final SchedulingAgentCallback schedulingAgentCallback) {
 
         final Processor processor = getProcessor();
         final ComponentLog procLog = new SimpleProcessLogger(StandardProcessorNode.this.getIdentifier(), processor);
@@ -1733,8 +1733,15 @@ public class StandardProcessorNode extends ProcessorNode implements Connectable
             if (validationStatus != ValidationStatus.VALID) {
                 LOG.debug("Cannot start {} because Processor is currently not valid; will try again after 5 seconds", StandardProcessorNode.this);
 
+                startupAttemptCount.incrementAndGet();
+                if (startupAttemptCount.get() == 240 || startupAttemptCount.get() % 7200 == 0) {
+                    final ValidationState validationState = getValidationState();
+                    procLog.error("Encountering difficulty starting. (Validation State is {}: {}). Will continue trying to start.",
+                            validationState, validationState.getValidationErrors());
+                }
+
                 // re-initiate the entire process
-                final Runnable initiateStartTask = () -> initiateStart(taskScheduler, administrativeYieldMillis, timeoutMilis, processContextFactory, schedulingAgentCallback);
+                final Runnable initiateStartTask = () -> initiateStart(taskScheduler, administrativeYieldMillis, timeoutMilis, startupAttemptCount, processContextFactory, schedulingAgentCallback);
                 taskScheduler.schedule(initiateStartTask, 500, TimeUnit.MILLISECONDS);
 
                 schedulingAgentCallback.onTaskComplete();
@@ -1811,7 +1818,7 @@ public class StandardProcessorNode extends ProcessorNode implements Connectable
                 // make sure we only continue retry loop if STOP action wasn't initiated
                 if (scheduledState.get() != ScheduledState.STOPPING && scheduledState.get() != ScheduledState.RUN_ONCE) {
                     // re-initiate the entire process
-                    final Runnable initiateStartTask = () -> initiateStart(taskScheduler, administrativeYieldMillis, timeoutMilis, processContextFactory, schedulingAgentCallback);
+                    final Runnable initiateStartTask = () -> initiateStart(taskScheduler, administrativeYieldMillis, timeoutMilis, startupAttemptCount, processContextFactory, schedulingAgentCallback);
                     taskScheduler.schedule(initiateStartTask, administrativeYieldMillis, TimeUnit.MILLISECONDS);
                 } else {
                     completeStopAction();
diff --git a/nifi-nar-bundles/nifi-framework-bundle/nifi-framework/nifi-framework-components/src/main/java/org/apache/nifi/controller/service/StandardControllerServiceNode.java b/nifi-nar-bundles/nifi-framework-bundle/nifi-framework/nifi-framework-components/src/main/java/org/apache/nifi/controller/service/StandardControllerServiceNode.java
index 95391be3b0..cde95fce9f 100644
--- a/nifi-nar-bundles/nifi-framework-bundle/nifi-framework/nifi-framework-components/src/main/java/org/apache/nifi/controller/service/StandardControllerServiceNode.java
+++ b/nifi-nar-bundles/nifi-framework-bundle/nifi-framework/nifi-framework-components/src/main/java/org/apache/nifi/controller/service/StandardControllerServiceNode.java
@@ -83,6 +83,7 @@ import java.util.concurrent.RejectedExecutionException;
 import java.util.concurrent.ScheduledExecutorService;
 import java.util.concurrent.TimeUnit;
 import java.util.concurrent.atomic.AtomicBoolean;
+import java.util.concurrent.atomic.AtomicLong;
 import java.util.concurrent.atomic.AtomicReference;
 import java.util.concurrent.locks.Lock;
 import java.util.concurrent.locks.ReadWriteLock;
@@ -574,6 +575,7 @@ public class StandardControllerServiceNode extends AbstractComponentNode impleme
 
             final ControllerServiceProvider controllerServiceProvider = this.serviceProvider;
             final StandardControllerServiceNode service = this;
+            AtomicLong enablingAttemptCount = new AtomicLong(0);
             scheduler.execute(new Runnable() {
                 @Override
                 public void run() {
@@ -592,6 +594,13 @@ public class StandardControllerServiceNode extends AbstractComponentNode impleme
                         LOG.debug("Cannot enable {} because it is not currently valid. (Validation State is {}: {}). Will try again in 1 second",
                             StandardControllerServiceNode.this, validationState, validationState.getValidationErrors());
 
+                        enablingAttemptCount.incrementAndGet();
+                        if (enablingAttemptCount.get() == 120 || enablingAttemptCount.get() % 3600 == 0) {
+                            final ComponentLog componentLog = new SimpleProcessLogger(getIdentifier(), StandardControllerServiceNode.this);
+                            componentLog.error("Encountering difficulty enabling. (Validation State is {}: {}). Will continue trying to enable.",
+                                    validationState, validationState.getValidationErrors());
+                        }
+
                         try {
                             scheduler.schedule(this, 1, TimeUnit.SECONDS);
                         } catch (RejectedExecutionException rejectedExecutionException) {