diff --git a/src/modules/features/ModuleLog.ts b/src/modules/features/ModuleLog.ts
index b614c11..a6f31a2 100644
--- a/src/modules/features/ModuleLog.ts
+++ b/src/modules/features/ModuleLog.ts
@@ -35,6 +35,12 @@ import { $msg } from "src/lib/src/common/i18n.ts";
 import { P2PLogCollector } from "../../lib/src/replication/trystero/P2PReplicatorCore.ts";
 import type { LiveSyncCore } from "../../main.ts";
 import { LiveSyncError } from "@/lib/src/common/LSError.ts";
+import { isValidPath } from "@/common/utils.ts";
+import {
+    isValidFilenameInAndroid,
+    isValidFilenameInDarwin,
+    isValidFilenameInWidows,
+} from "@/lib/src/string_and_binary/path.ts";
 
 // This module cannot be a core module because it depends on the Obsidian UI.
 
@@ -229,19 +235,45 @@ export class ModuleLog extends AbstractObsidianModule {
     }
 
     async getActiveFileStatus() {
+        const reason = [] as string[];
+        const reasonWarn = [] as string[];
         const thisFile = this.app.workspace.getActiveFile();
         if (!thisFile) return "";
+        const validPath = isValidPath(thisFile.path);
+        if (!validPath) {
+            reason.push("This file has an invalid path under the current settings");
+        } else {
+            // The most narrow check: Filename validity on Windows
+            const validOnWindows = isValidFilenameInWidows(thisFile.name);
+            const validOnDarwin = isValidFilenameInDarwin(thisFile.name);
+            const validOnAndroid = isValidFilenameInAndroid(thisFile.name);
+            const labels = [];
+            if (!validOnWindows) labels.push("🪟");
+            if (!validOnDarwin) labels.push("🍎");
+            if (!validOnAndroid) labels.push("🤖");
+            if (labels.length > 0) {
+                reasonWarn.push("Some platforms may be unable to process this file correctly: " + labels.join(" "));
+            }
+        }
         // Case Sensitivity
         if (this.services.setting.shouldCheckCaseInsensitively()) {
             const f = this.core.storageAccess
                 .getFiles()
                 .map((e) => e.path)
                 .filter((e) => e.toLowerCase() == thisFile.path.toLowerCase());
-            if (f.length > 1) return "Not synchronised: There are multiple files with the same name";
+            if (f.length > 1) {
+                reason.push("There are multiple files with the same name (case-insensitive match)");
+            }
         }
-        if (!(await this.services.vault.isTargetFile(thisFile.path))) return "Not synchronised: not a target file";
-        if (this.services.vault.isFileSizeTooLarge(thisFile.stat.size)) return "Not synchronised: File size exceeded";
-        return "";
+        if (!(await this.services.vault.isTargetFile(thisFile.path))) {
+            reason.push("This file is ignored by the ignore rules");
+        }
+        if (this.services.vault.isFileSizeTooLarge(thisFile.stat.size)) {
+            reason.push("This file size exceeds the configured limit");
+        }
+        const result = reason.length > 0 ? "Not synchronised: " + reason.join(", ") : "";
+        const warnResult = reasonWarn.length > 0 ? "Warning: " + reasonWarn.join(", ") : "";
+        return [result, warnResult].filter((e) => e).join("\n");
     }
     async setFileStatus() {
         const fileStatus = await this.getActiveFileStatus();