diff --git a/niri/files/copy-latest-screenshot.sh b/niri/files/copy-latest-screenshot.sh
index b577380..6a55798 100755
--- a/niri/files/copy-latest-screenshot.sh
+++ b/niri/files/copy-latest-screenshot.sh
@@ -1,8 +1,11 @@
 #!/usr/bin/env bash
 
+set -u
+
 screenshot_dir="$HOME/Pictures/Screenshots"
 remote_target="mac-attio:~/screenshot.png"
-timeout=3  # seconds
+file_timeout=8   # seconds to wait for screenshot file to appear
+upload_timeout=10  # seconds
 
 notify() {
   DBUS_SESSION_BUS_ADDRESS="unix:path=/run/user/$(id -u)/bus" \
@@ -15,12 +18,13 @@ shopt -s nullglob
 existing_files=("$screenshot_dir"/*.png)
 existing_count=${#existing_files[@]}
 
-# Take screenshot
-niri msg action screenshot
+# Take screenshot (no timeout here so interactive capture isn't canceled)
+niri msg action screenshot >/dev/null 2>&1
 
 # Wait for new file (timeout in 0.1s intervals)
-deadline=$((timeout * 10))
+deadline=$((file_timeout * 10))
 count=0
+files=("$screenshot_dir"/*.png)
 
 while (( count < deadline )); do
   files=("$screenshot_dir"/*.png)
@@ -37,12 +41,20 @@ if (( ${#files[@]} <= existing_count )); then
 fi
 
 # Get the new file (most recent)
-latest_file=$(ls -1t "${files[@]}" | head -n 1)
+latest_file=$(ls -1t -- "${files[@]}" | head -n 1)
 
 # Small delay to ensure file is fully written
 sleep 0.1
 
-# Upload
-if scp -q "$latest_file" "$remote_target"; then
+# Upload with strict SSH options so it never blocks waiting for prompts
+if timeout "${upload_timeout}s" scp -q \
+  -o BatchMode=yes \
+  -o ConnectTimeout=5 \
+  -o ConnectionAttempts=1 \
+  -o ServerAliveInterval=2 \
+  -o ServerAliveCountMax=1 \
+  -- "$latest_file" "$remote_target"; then
   notify "Screenshot" "Uploaded to Mac"
+else
+  notify "Screenshot" "Upload to Mac failed"
 fi