diff --git a/src-tauri/src/commands/analysis.rs b/src-tauri/src/commands/analysis.rs
index fcc97cf4..24a24031 100644
--- a/src-tauri/src/commands/analysis.rs
+++ b/src-tauri/src/commands/analysis.rs
@@ -60,10 +60,12 @@ const SAFE_TEXT_EXTENSIONS: &[&str] = &[
 
 const SAFE_BINARY_EXTENSIONS: &[&str] = &["pdf", "docx", "doc", "xlsx", "xls"];
 
-fn compress_text(text: &str) -> Vec<u8> {
+fn compress_text(text: &str) -> Result<Vec<u8>, String> {
     let mut encoder = GzEncoder::new(Vec::new(), Compression::default());
-    encoder.write_all(text.as_bytes()).unwrap_or_default();
-    encoder.finish().unwrap_or_default()
+    encoder
+        .write_all(text.as_bytes())
+        .map_err(|e| format!("Compression write error: {e}"))?;
+    encoder.finish().map_err(|e| format!("Compression finish error: {e}"))
 }
 
 /// 100 MB cap — prevents decompression-bomb attacks on crafted DB entries.
@@ -256,7 +258,8 @@ pub async fn upload_log_file(
         ..log_file
     };
 
-    let compressed = compress_text(&extracted_text);
+    let compressed = compress_text(&extracted_text)
+        .map_err(|e| format!("Failed to compress log content: {e}"))?;
 
     let db = state.db.lock().map_err(|e| e.to_string())?;
     db.execute(
@@ -349,7 +352,8 @@ pub async fn upload_log_file_by_content(
         ..log_file
     };
 
-    let compressed = compress_text(&content);
+    let compressed = compress_text(&content)
+        .map_err(|e| format!("Failed to compress log content: {e}"))?;
 
     let db = state.db.lock().map_err(|e| e.to_string())?;
     db.execute(
@@ -682,17 +686,27 @@ mod tests {
     #[test]
     fn test_compress_decompress_roundtrip() {
         let original = "Hello, World! This is a log line with some content.";
-        let compressed = compress_text(original);
+        let compressed = compress_text(original).unwrap();
         assert!(!compressed.is_empty());
         assert!(compressed.len() < original.len() * 3);
         let decompressed = decompress_text(&compressed).unwrap();
         assert_eq!(decompressed, original);
     }
 
+    #[test]
+    fn test_compress_returns_error_not_empty_on_failure() {
+        // compress_text returns Result — callers must propagate, not silently discard.
+        // For in-memory gzip this essentially never fails, but the API now allows
+        // callers to surface the error rather than storing empty bytes.
+        let result = compress_text("normal log line");
+        assert!(result.is_ok(), "compress_text should succeed for normal input");
+        assert!(!result.unwrap().is_empty());
+    }
+
     #[test]
     fn test_compress_large_text_is_smaller() {
         let original = "INFO server started\n".repeat(1000);
-        let compressed = compress_text(&original);
+        let compressed = compress_text(&original).unwrap();
         assert!(
             compressed.len() < original.len(),
             "gzip should compress repetitive text"
@@ -707,9 +721,6 @@ mod tests {
 
     #[test]
     fn test_decompress_size_limit_enforced() {
-        // Create a compressible payload that when decompressed exceeds the limit.
-        // We mock the limit by creating a large repetitive string and checking the
-        // round-trip succeeds, then verify the limit constant is set correctly.
         assert_eq!(
             MAX_DECOMPRESSED_BYTES,
             100 * 1024 * 1024,
@@ -718,7 +729,7 @@ mod tests {
 
         // A valid small payload must still decompress fine after the guard is in place.
         let text = "hello world decompression guard test\n".repeat(100);
-        let compressed = compress_text(&text);
+        let compressed = compress_text(&text).unwrap();
         let result = decompress_text(&compressed);
         assert!(result.is_ok());
         assert_eq!(result.unwrap(), text);
diff --git a/src-tauri/src/commands/image.rs b/src-tauri/src/commands/image.rs
index 79a5e1bc..60cec096 100644
--- a/src-tauri/src/commands/image.rs
+++ b/src-tauri/src/commands/image.rs
@@ -140,6 +140,13 @@ pub async fn upload_image_attachment_by_content(
         .decode(data_part)
         .map_err(|_| "Failed to decode base64 image data")?;
 
+    if decoded.len() as u64 > MAX_IMAGE_FILE_BYTES {
+        return Err(format!(
+            "Image content exceeds maximum supported size ({} MB)",
+            MAX_IMAGE_FILE_BYTES / 1024 / 1024
+        ));
+    }
+
     let content_hash = format!("{:x}", sha2::Sha256::digest(&decoded));
     let file_size = decoded.len() as i64;
 
@@ -231,6 +238,13 @@ pub async fn upload_paste_image(
         .decode(data_part)
         .map_err(|_| "Failed to decode base64 image data")?;
 
+    if decoded.len() as u64 > MAX_IMAGE_FILE_BYTES {
+        return Err(format!(
+            "Pasted image exceeds maximum supported size ({} MB)",
+            MAX_IMAGE_FILE_BYTES / 1024 / 1024
+        ));
+    }
+
     let content_hash = format!("{:x}", sha2::Sha256::digest(&decoded));
     let file_size = decoded.len() as i64;
     let file_name = format!("pasted-image-{}.png", uuid::Uuid::now_v7());
diff --git a/src/pages/History/index.tsx b/src/pages/History/index.tsx
index 17cbe7ec..be81a9c3 100644
--- a/src/pages/History/index.tsx
+++ b/src/pages/History/index.tsx
@@ -259,6 +259,7 @@ function AttachmentsTab({ navigate }: { navigate: ReturnType<typeof useNavigate>
 
   const [viewModal, setViewModal] = useState<{ type: "log" | "image"; id: string; title: string } | null>(null);
   const [modalContent, setModalContent] = useState<string | null>(null);
+  const [modalError, setModalError] = useState<string | null>(null);
   const [modalLoading, setModalLoading] = useState(false);
 
   useEffect(() => {
@@ -290,12 +291,13 @@ function AttachmentsTab({ navigate }: { navigate: ReturnType<typeof useNavigate>
   const openImageModal = async (id: string, fileName: string) => {
     setViewModal({ type: "image", id, title: fileName });
     setModalContent(null);
+    setModalError(null);
     setModalLoading(true);
     try {
       const dataUrl = await getImageAttachmentDataCmd(id);
       setModalContent(dataUrl);
     } catch (e) {
-      setModalContent(null);
+      setModalError(String(e));
     } finally {
       setModalLoading(false);
     }
@@ -304,6 +306,7 @@ function AttachmentsTab({ navigate }: { navigate: ReturnType<typeof useNavigate>
   const closeModal = () => {
     setViewModal(null);
     setModalContent(null);
+    setModalError(null);
   };
 
   const formatBytes = (bytes: number) => {
@@ -510,7 +513,12 @@ function AttachmentsTab({ navigate }: { navigate: ReturnType<typeof useNavigate>
                 />
               )}
               {!modalLoading && viewModal.type === "image" && !modalContent && (
-                <div className="text-center text-muted-foreground py-8">Image could not be loaded.</div>
+                <div className="text-center py-8 space-y-2">
+                  <div className="text-muted-foreground">Image could not be loaded.</div>
+                  {modalError && (
+                    <div className="text-xs text-destructive font-mono">{modalError}</div>
+                  )}
+                </div>
               )}
             </div>
           </div>