diff --git a/lib/nip95.ts b/lib/nip95.ts
index e399776..aa57575 100644
--- a/lib/nip95.ts
+++ b/lib/nip95.ts
@@ -131,12 +131,19 @@ export async function uploadNip95Media(file: File): Promise<MediaRef> {
       const error = e instanceof Error ? e : new Error(String(e))
       const errorMessage = error.message
 
-      // If CORS error, network error, or 405 error, try via proxy
+      // If CORS error, network error, 405 error, or name resolution error, try via proxy
       const isCorsError = errorMessage.includes('CORS') || errorMessage.includes('Failed to fetch')
       const isMethodNotAllowed = errorMessage.includes('405') || errorMessage.includes('Method Not Allowed')
-      if (isCorsError || isMethodNotAllowed) {
+      const isNameResolutionError = errorMessage.includes('ERR_NAME_NOT_RESOLVED') || errorMessage.includes('getaddrinfo')
+      const shouldUseProxy = isCorsError || isMethodNotAllowed || isNameResolutionError
+
+      if (shouldUseProxy) {
         try {
-          console.log('Trying upload via proxy due to error:', endpoint, isCorsError ? 'CORS' : 'Method Not Allowed')
+          console.log('Trying upload via proxy due to error:', endpoint, {
+            CORS: isCorsError,
+            'Method Not Allowed': isMethodNotAllowed,
+            'Name Resolution': isNameResolutionError,
+          })
           // Pass endpoint as query parameter to proxy
           const proxyUrl = `/api/nip95-upload?endpoint=${encodeURIComponent(endpoint)}`
           const url = await tryUploadEndpoint(proxyUrl, formData, true)
diff --git a/pages/api/nip95-upload.ts b/pages/api/nip95-upload.ts
index b67f6dc..8b655e6 100644
--- a/pages/api/nip95-upload.ts
+++ b/pages/api/nip95-upload.ts
@@ -62,13 +62,33 @@ export default async function handler(req: NextApiRequest, res: NextApiResponse)
     })
 
     // Forward to target endpoint
-    const response = await fetch(targetEndpoint, {
-      method: 'POST',
-      body: formData as unknown as BodyInit,
-      headers: {
-        ...formData.getHeaders(),
-      },
-    })
+    let response: Response
+    try {
+      response = await fetch(targetEndpoint, {
+        method: 'POST',
+        body: formData as unknown as BodyInit,
+        headers: {
+          ...formData.getHeaders(),
+        },
+      })
+    } catch (fetchError) {
+      // Clean up temporary file before returning error
+      try {
+        fs.unlinkSync(fileField.filepath)
+      } catch (unlinkError) {
+        console.error('Error deleting temp file:', unlinkError)
+      }
+      const errorMessage = fetchError instanceof Error ? fetchError.message : 'Unknown fetch error'
+      console.error('NIP-95 proxy fetch error:', {
+        targetEndpoint,
+        error: errorMessage,
+        fileSize: fileField.size,
+        fileName: fileField.originalFilename,
+      })
+      return res.status(500).json({
+        error: `Failed to connect to upload endpoint: ${errorMessage}`,
+      })
+    }
 
     // Clean up temporary file
     try {
@@ -79,6 +99,12 @@ export default async function handler(req: NextApiRequest, res: NextApiResponse)
 
     if (!response.ok) {
       const errorText = await response.text()
+      console.error('NIP-95 proxy response error:', {
+        targetEndpoint,
+        status: response.status,
+        statusText: response.statusText,
+        errorText: errorText.substring(0, 200), // Limit log size
+      })
       return res.status(response.status).json({
         error: errorText || `Upload failed: ${response.status} ${response.statusText}`,
       })