diff --git a/src/main.d b/src/main.d
index bf88b65b..ddad65f1 100644
--- a/src/main.d
+++ b/src/main.d
@@ -734,6 +734,9 @@ int main(string[] args)
 	
 	// Are we performing a sync, or monitor operation?
 	if ((cfg.getValueBool("synchronize")) || (cfg.getValueBool("monitor"))) {
+		// Initialise the monitor class, so that we can do more granular inotify handling when performing the actual sync
+		// needed for --synchronize and --monitor handling
+		Monitor m = new Monitor(selectiveSync);
 
 		if (cfg.getValueBool("synchronize")) {
 			if (online) {
@@ -750,14 +753,14 @@ int main(string[] args)
 				// perform a --synchronize sync
 				// fullScanRequired = false, for final true-up
 				// but if we have sync_list configured, use syncListConfigured which = true
-				performSync(sync, cfg.getValueString("single_directory"), cfg.getValueBool("download_only"), cfg.getValueBool("local_first"), cfg.getValueBool("upload_only"), LOG_NORMAL, false, syncListConfigured, displaySyncOptions);
+				performSync(sync, cfg.getValueString("single_directory"), cfg.getValueBool("download_only"), cfg.getValueBool("local_first"), cfg.getValueBool("upload_only"), LOG_NORMAL, false, syncListConfigured, displaySyncOptions, cfg.getValueBool("monitor"), m);
 			}
 		}
 			
 		if (cfg.getValueBool("monitor")) {
 			log.logAndNotify("Initializing monitor ...");
 			log.log("OneDrive monitor interval (seconds): ", cfg.getValueLong("monitor_interval"));
-			Monitor m = new Monitor(selectiveSync);
+			
 			m.onDirCreated = delegate(string path) {
 				// Handle .folder creation if skip_dotfiles is enabled
 				if ((cfg.getValueBool("skip_dotfiles")) && (selectiveSync.isDotFile(path))) {
@@ -925,9 +928,9 @@ int main(string[] args)
 						try {
 							// perform a --monitor sync
 							log.vlog("Starting a sync with OneDrive");
-							performSync(sync, cfg.getValueString("single_directory"), cfg.getValueBool("download_only"), cfg.getValueBool("local_first"), cfg.getValueBool("upload_only"), (logMonitorCounter == logInterval ? MONITOR_LOG_QUIET : MONITOR_LOG_SILENT), fullScanRequired, syncListConfiguredFullScanOverride, displaySyncOptions);
+							performSync(sync, cfg.getValueString("single_directory"), cfg.getValueBool("download_only"), cfg.getValueBool("local_first"), cfg.getValueBool("upload_only"), (logMonitorCounter == logInterval ? MONITOR_LOG_QUIET : MONITOR_LOG_SILENT), fullScanRequired, syncListConfiguredFullScanOverride, displaySyncOptions, cfg.getValueBool("monitor"), m);
 							if (!cfg.getValueBool("download_only")) {
-								// discard all events that may have been generated by the sync
+								// discard all events that may have been generated by the sync that have not already been handled
 								try {
 									m.update(false);
 								} catch (MonitorException e) {
@@ -935,6 +938,7 @@ int main(string[] args)
 									log.error("ERROR: The following inotify error was generated: ", e.msg);
 								}
 							}
+							log.vlog("Sync with OneDrive is complete");
 						} catch (CurlException e) {
 							// we already tried three times in the performSync routine
 							// if we still have problems, then the sync handle might have
@@ -946,7 +950,6 @@ int main(string[] args)
 						log.log("Cannot initialize connection to OneDrive");
 					}
 					// performSync complete, set lastCheckTime to current time
-					log.vlog("Sync with OneDrive is complete");
 					fullScanRequired = false;
 					if (syncListConfigured) {
 						syncListConfiguredFullScanOverride = false;
@@ -1016,7 +1019,7 @@ bool initSyncEngine(SyncEngine sync)
 }
 
 // try to synchronize the folder three times
-void performSync(SyncEngine sync, string singleDirectory, bool downloadOnly, bool localFirst, bool uploadOnly, long logLevel, bool fullScanRequired, bool syncListConfiguredFullScanOverride, bool displaySyncOptions)
+void performSync(SyncEngine sync, string singleDirectory, bool downloadOnly, bool localFirst, bool uploadOnly, long logLevel, bool fullScanRequired, bool syncListConfiguredFullScanOverride, bool displaySyncOptions, bool monitorEnabled, Monitor m)
 {
 	int count;
 	string remotePath = "/";
@@ -1131,7 +1134,27 @@ void performSync(SyncEngine sync, string singleDirectory, bool downloadOnly, boo
 								log.vdebug(logOutputMessage);
 								log.vdebug(syncCallLogOutput);
 							}
-							sync.scanForDifferences(localPath);
+							
+							// What sort of local scan do we want to do?
+							// In --monitor mode, when performing the DB scan, a race condition occurs where by if a file or folder is moved during this process
+							// the inotify event is discarded once performSync() is finished (see m.update(false) above), so these events need to be handled
+							// This can be remediated by breaking the DB and file system scan into separate processes, and handing any applicable inotify events in between
+							if (!monitorEnabled) {
+								// --synchronize in use
+								// standard process flow
+								sync.scanForDifferences(localPath);
+							} else {
+								// --monitor in use
+								// Use individual calls with inotify checks between to avoid a race condition between these 2 functions
+								// Database scan
+								sync.scanForDifferencesDatabaseScan(localPath);
+								// handle any inotify events that occured 'whilst' we were scanning the database
+								m.update(true);
+								// Filesystem walk to find new files not uploaded
+								sync.scanForDifferencesFilesystemScan(localPath);
+								// handle any inotify events that occured 'whilst' we were scanning the local filesystem
+								m.update(true);
+							}
 							
 							// At this point, all OneDrive changes / local changes should be uploaded and in sync
 							// This MAY not be the case when using sync_list, thus a full walk of OneDrive ojects is required
diff --git a/src/sync.d b/src/sync.d
index de311cc7..3471e3cb 100644
--- a/src/sync.d
+++ b/src/sync.d
@@ -2243,19 +2243,40 @@ final class SyncEngine
 		log.vlog("Uploading differences of ", path);
 		Item item;
 		if (itemdb.selectByPath(path, defaultDriveId, item)) {
+			// Database scan of every item in DB, does it still exist on disk in the location the DB thinks it is
 			uploadDifferences(item);
 		}
 		
 		log.vlog("Uploading new items of ", path);
+		// Filesystem walk to find new files not uploaded
 		uploadNewItems(path);
-		
 		// clean up idsToDelete only if --dry-run is set
 		if (dryRun) {
 			idsToDelete.length = 0;
 			assumeSafeAppend(idsToDelete);
 		}
 	}
-
+	
+	// scan the given directory for differences only - for use with --monitor
+	void scanForDifferencesDatabaseScan(const(string) path)
+	{
+		// scan for changes in the path provided
+		log.vlog("Uploading differences of ", path);
+		Item item;
+		if (itemdb.selectByPath(path, defaultDriveId, item)) {
+			// Database scan of every item in DB, does it still exist on disk in the location the DB thinks it is
+			uploadDifferences(item);
+		}
+	}
+	
+	// scan the given directory for new items - for use with --monitor
+	void scanForDifferencesFilesystemScan(const(string) path)
+	{
+		log.vlog("Uploading new items of ", path);
+		// Filesystem walk to find new files not uploaded
+		uploadNewItems(path);
+	}
+	
 	private void uploadDifferences(const ref Item item)
 	{
 		// see if this item.id we were supposed to have deleted
@@ -2342,12 +2363,19 @@ final class SyncEngine
 			// Directory does not exist locally
 			// If we are in a --dry-run situation - this directory may never have existed as we never downloaded it
 			if (!dryRun) {
-				log.vlog("The directory has been deleted locally");
-				if (noRemoteDelete) {
-					// do not process remote directory delete
-					log.vlog("Skipping remote directory delete as --upload-only & --no-remote-delete configured");
+				// Not --dry-run situation
+				if (!cfg.getValueBool("monitor")) {
+					// Not in --monitor mode
+					log.vlog("The directory has been deleted locally");
+					if (noRemoteDelete) {
+						// do not process remote directory delete
+						log.vlog("Skipping remote directory delete as --upload-only & --no-remote-delete configured");
+					} else {
+						uploadDeleteItem(item, path);
+					}	
 				} else {
-					uploadDeleteItem(item, path);
+					// Appropriate message as we are in --monitor mode
+					log.vlog("The directory appears to have been deleted locally .. but we are running in --monitor mode. This may have been 'moved' rather than 'deleted'");
 				}
 			} else {
 				// we are in a --dry-run situation, directory appears to have deleted locally - this directory may never have existed as we never downloaded it ..
@@ -2750,12 +2778,17 @@ final class SyncEngine
 			// If we are in a --dry-run situation - this file may never have existed as we never downloaded it
 			if (!dryRun) {
 				// Not --dry-run situation
-				log.vlog("The file has been deleted locally");
-				if (noRemoteDelete) {
-					// do not process remote file delete
-					log.vlog("Skipping remote file delete as --upload-only & --no-remote-delete configured");
+				if (!cfg.getValueBool("monitor")) {
+					log.vlog("The file has been deleted locally");
+					if (noRemoteDelete) {
+						// do not process remote file delete
+						log.vlog("Skipping remote file delete as --upload-only & --no-remote-delete configured");
+					} else {
+						uploadDeleteItem(item, path);
+					}
 				} else {
-					uploadDeleteItem(item, path);
+					// Appropriate message as we are in --monitor mode
+					log.vlog("The file appears to have been deleted locally .. but we are running in --monitor mode. This may have been 'moved' rather than 'deleted'");
 				}
 			} else {
 				// We are in a --dry-run situation, file appears to have deleted locally - this file may never have existed as we never downloaded it ..