diff --git a/Core/src/com/basistech/df/cybertriage/autopsy/malwarescan/Bundle.properties-MERGED b/Core/src/com/basistech/df/cybertriage/autopsy/malwarescan/Bundle.properties-MERGED
index a03690feed1f7207b9548a0eca141e1f85072139..9aecc568dfe5063bca9eddbb1406627034079330 100644
--- a/Core/src/com/basistech/df/cybertriage/autopsy/malwarescan/Bundle.properties-MERGED
+++ b/Core/src/com/basistech/df/cybertriage/autopsy/malwarescan/Bundle.properties-MERGED
@@ -33,6 +33,11 @@ MalwareScanIngestModule_ShareProcessing_noLookupsRemaining_desc=There are no mor
 MalwareScanIngestModule_ShareProcessing_noLookupsRemaining_title=No remaining lookups
 MalwareScanIngestModule_ShareProcessing_noUploadsRemaining_desc=There are no more remaining file uploads for this license at this time.  File uploading will be disabled.
 MalwareScanIngestModule_ShareProcessing_noUploadsRemaining_title=No remaining file uploads
+MalwareScanIngestModule_uploadFile_noRemainingFileUploads_desc=There are no more file uploads on this license at this time.  File uploads will be disabled for remaining uploads.
+MalwareScanIngestModule_uploadFile_noRemainingFileUploads_title=No Remaining File Uploads
+# {0} - objectId
+MalwareScanIngestModule_uploadFile_notUploadable_desc=A file did not meet requirements for upload (object id: {0}).
+MalwareScanIngestModule_uploadFile_notUploadable_title=Not Able to Upload
 MalwareScanIngestModuleFactory_description=The malware scan ingest module queries the Cyber Triage cloud API for any possible malicious executables.
 MalwareScanIngestModuleFactory_displayName=Cyber Triage Malware Scanner
 MalwareScanIngestModuleFactory_version=1.0.0
diff --git a/Core/src/com/basistech/df/cybertriage/autopsy/malwarescan/MalwareScanIngestModule.java b/Core/src/com/basistech/df/cybertriage/autopsy/malwarescan/MalwareScanIngestModule.java
index f528feb6533ffc708d99926a923e531f95c857a0..9b69226c58b823d07b3513d901e274b0024728ef 100644
--- a/Core/src/com/basistech/df/cybertriage/autopsy/malwarescan/MalwareScanIngestModule.java
+++ b/Core/src/com/basistech/df/cybertriage/autopsy/malwarescan/MalwareScanIngestModule.java
@@ -27,7 +27,6 @@
 import com.basistech.df.cybertriage.autopsy.ctapi.json.MalwareResultBean.Status;
 import com.basistech.df.cybertriage.autopsy.ctapi.json.MetadataUploadRequest;
 import com.basistech.df.cybertriage.autopsy.ctoptions.ctcloud.CTLicensePersistence;
-import java.security.DigestInputStream;
 import java.security.MessageDigest;
 import java.security.NoSuchAlgorithmException;
 import java.text.MessageFormat;
@@ -559,6 +558,18 @@ private List<CTCloudBean> getHashLookupResults(IngestJobState ingestJobState, Li
             } else if (ingestJobState.getIngestJobContext().fileIngestIsCancelled()) {
                 return Collections.emptyList();
             }
+            
+            // while we have a valid auth token, also check file uploads.
+            if (ingestJobState.isUploadUnknownFiles()) {
+                long remainingUploads = remaining(authTokenResponse.getFileUploadLimit(), authTokenResponse.getHashLookupCount());
+                if (remainingUploads <= 0) {
+                    ingestJobState.disableUploadUnknownFiles();
+                    notifyWarning(
+                        Bundle.MalwareScanIngestModule_uploadFile_noRemainingFileUploads_title(),
+                        Bundle.MalwareScanIngestModule_uploadFile_noRemainingFileUploads_desc(),
+                        null);
+                }
+            }
 
             // using auth token, get results
             return ctApiDAO.getReputationResults(
@@ -598,13 +609,27 @@ private static boolean isUploadable(AbstractFile af) {
          * @throws CTCloudException
          * @throws TskCoreException
          */
+        @Messages({
+            "MalwareScanIngestModule_uploadFile_notUploadable_title=Not Able to Upload",
+            "# {0} - objectId",
+            "MalwareScanIngestModule_uploadFile_notUploadable_desc=A file did not meet requirements for upload (object id: {0}).",
+            "MalwareScanIngestModule_uploadFile_noRemainingFileUploads_title=No Remaining File Uploads",
+            "MalwareScanIngestModule_uploadFile_noRemainingFileUploads_desc=There are no more file uploads on this license at this time.  File uploads will be disabled for remaining uploads.",})
         private boolean uploadFile(IngestJobState ingestJobState, String md5, long objId) throws CTCloudException, TskCoreException, NoSuchAlgorithmException, ReadContentInputStream.ReadContentInputStreamException {
             if (!ingestJobState.isUploadUnknownFiles() || ingestJobState.getIngestJobContext().fileIngestIsCancelled()) {
                 return false;
             }
 
             AbstractFile af = ingestJobState.getTskCase().getAbstractFileById(objId);
-            if (af == null || !isUploadable(af)) {
+            if (af == null) {
+                return false;
+            }
+
+            if (!isUploadable(af)) {
+                notifyWarning(
+                        Bundle.MalwareScanIngestModule_uploadFile_notUploadable_title(),
+                        Bundle.MalwareScanIngestModule_uploadFile_notUploadable_desc(objId),
+                        null);
                 return false;
             }
 
@@ -615,6 +640,11 @@ private boolean uploadFile(IngestJobState ingestJobState, String md5, long objId
             } else if (remaining(authTokenResponse.getFileUploadLimit(), authTokenResponse.getFileUploadCount()) <= 0) {
                 // don't proceed with upload if reached limit
                 ingestJobState.disableUploadUnknownFiles();
+                notifyWarning(
+                        Bundle.MalwareScanIngestModule_uploadFile_noRemainingFileUploads_title(),
+                        Bundle.MalwareScanIngestModule_uploadFile_noRemainingFileUploads_desc(),
+                        null);
+
                 return false;
             } else if (ingestJobState.getIngestJobContext().fileIngestIsCancelled()) {
                 return false;
@@ -640,6 +670,7 @@ private boolean uploadFile(IngestJobState ingestJobState, String md5, long objId
 
         /**
          * Does long polling for any pending results.
+         *
          * @param ingestJobState The state of the ingest job.
          * @throws InterruptedException
          * @throws CTCloudException