diff --git a/scripts/env.sh b/scripts/env.sh
index 08456f9..b0c48c1 100755
--- a/scripts/env.sh
+++ b/scripts/env.sh
@@ -88,13 +88,60 @@ nix_extra_opts() {
   fi
   export NIX_EXTRA_OPTS_DECIDED=1
   NIX_OPTS=()
-  if ! curl --silent --fail --max-time 3 "http://${NIX_CACHE_HOST}/nix-cache-info" >/dev/null 2>&1; then
+
+  # Retry a couple of times, 1s apart, before believing either check --
+  # belt-and-suspenders against a genuine multi-second blip (nix-cache
+  # restarting), on top of the fix below. Worst case (~11s total, host
+  # genuinely gone) is still nowhere near the 15s+ *per lookup* nix's own
+  # substituter retries would cost if this check didn't exist at all.
+  local attempt cache_up=0 builder_up=0
+  for attempt in 1 2 3; do
+    if curl --silent --fail --max-time 3 "http://${NIX_CACHE_HOST}/nix-cache-info" >/dev/null 2>&1; then
+      cache_up=1
+      break
+    fi
+    [[ "$attempt" -lt 3 ]] && sleep 1
+  done
+
+  if [[ "$cache_up" -eq 0 ]]; then
     echo "nix-cache (http://${NIX_CACHE_HOST}) is unreachable -- skipping it (substituter + remote builder) for the rest of this run." >&2
     NIX_OPTS=(--option substituters "https://cache.nixos.org/" --builders "")
-  elif ! timeout 3 bash -c "cat < /dev/tcp/${NIX_CACHE_HOST}/22" >/dev/null 2>&1; then
-    echo "nix-cache's SSH remote builder (nixremote@${NIX_CACHE_HOST}:22) is unreachable -- disabling remote builds for the rest of this run." >&2
-    NIX_OPTS=(--builders "")
+  else
+    for attempt in 1 2 3; do
+      # `exec 3<>/dev/tcp/...` just opens the fd and returns -- it does NOT
+      # read from it. Confirmed live this is load-bearing, not stylistic:
+      # the previous `cat < /dev/tcp/.../22` blocked forever and always hit
+      # the timeout even against a perfectly healthy nix-cache, because
+      # sshd sends its banner and then holds the connection open waiting
+      # for the client to speak next -- `cat` never sees EOF, so this
+      # check reported "unreachable" unconditionally, 100% of the time,
+      # regardless of whether the remote builder was actually up.
+      if timeout 3 bash -c "exec 3<>/dev/tcp/${NIX_CACHE_HOST}/22" 2>/dev/null; then
+        builder_up=1
+        break
+      fi
+      [[ "$attempt" -lt 3 ]] && sleep 1
+    done
+    if [[ "$builder_up" -eq 0 ]]; then
+      echo "nix-cache's SSH remote builder (nixremote@${NIX_CACHE_HOST}:22) is unreachable -- disabling remote builds for the rest of this run." >&2
+      NIX_OPTS=(--builders "")
+    fi
+  fi
+
+  # `printf '%q '` with a genuinely empty NIX_OPTS still runs one format
+  # pass over a missing argument and yields the literal `'' ` rather than
+  # an empty string (confirmed live) -- a subprocess that later does
+  # `eval "NIX_OPTS=(${NIX_EXTRA_OPTS})"` (the branch above, for e.g.
+  # sync-host-keys.sh reusing this process's decision) would then rebuild
+  # a 1-element array holding an empty string instead of a 0-element
+  # array, and `nix-shell "${NIX_OPTS[@]}" -p <pkg>` chokes on that stray
+  # element as a bogus positional argument. Guard the empty case
+  # explicitly so nix-cache being reachable (NIX_OPTS legitimately empty)
+  # round-trips as truly empty instead.
+  if [[ ${#NIX_OPTS[@]} -gt 0 ]]; then
+    printf -v NIX_EXTRA_OPTS '%q ' "${NIX_OPTS[@]}"
+  else
+    NIX_EXTRA_OPTS=""
   fi
-  printf -v NIX_EXTRA_OPTS '%q ' "${NIX_OPTS[@]}"
   export NIX_EXTRA_OPTS
 }