diff --git a/.envrc b/.envrc
index 692b0fb..c385316 100644
--- a/.envrc
+++ b/.envrc
@@ -1,4 +1,4 @@
-watch_file devshell/{default,commands,install,vm-tasks}.nix
+watch_file devshell/*
 # --accept-flake-config trusts the flake's nixConfig (our Harmonia cache) non-interactively, so
 # direnv doesn't stall on the trust prompt.
 use flake . --accept-flake-config
diff --git a/.gitignore b/.gitignore
index b0efdb3..3132de3 100644
--- a/.gitignore
+++ b/.gitignore
@@ -1,4 +1,5 @@
 .direnv
+/.cache
 result*
 /.vms/*
 !/.vms/.gitkeep
diff --git a/AGENTS.md b/AGENTS.md
index 4336849..354ec92 100644
--- a/AGENTS.md
+++ b/AGENTS.md
@@ -55,7 +55,10 @@ Common ones:
   reboot to cut over.
 - `ssh-machine <name> [cmd]` — SSH to a NixOS system or home-manager config by name. Resolves the
   target and ssh options (identity, port) from its deploy-rs node, so it needs `my.deploy.enable`
-  (same gate as `deploy`). Boxes default to the `fish` login shell, so pipe multi-statement remote
+  (same gate as `deploy`). Connection settings for all nodes are cached together and invalidated
+  by tracked Git changes; use `ssh-machine --refresh` to force a refresh
+  (see `docs/deployment.md#ssh-machine`).
+  Boxes default to the `fish` login shell, so pipe multi-statement remote
   scripts through `bash` (e.g. `ssh-machine <name> bash -s < script.sh`) rather than `&&`/`for`.
   If outbound SSH hangs at the publickey step (flaky `ssh-agent`), disable the agent for the call:
   `SSH_AUTH_SOCK= ssh-machine …` (or add `-o IdentityAgent=none` to a raw `ssh`).
@@ -207,6 +210,8 @@ in churn.
 - Comment where it genuinely aids understanding, but not for trivial/obvious code — match the file's
   existing (fairly sparse) comment density. When adding something general, comment its general
   purpose, not the specific change or one-off reason it was introduced for.
+- Separate logical steps in code with blank lines. Keep closely related statements together, and leave a
+  blank line before a comment that introduces the next step.
 - Prefer `lib.my` helpers (`mkOpt'`, `mkBoolOpt'`, `mkDefault'`) and `lib.my.c` constants over
   reimplementing.
 - New shared functionality → a module in `*/modules/` + entry in `_list.nix`, options under `my.*`.
diff --git a/devshell/commands.nix b/devshell/commands.nix
index 523f24b..5980792 100644
--- a/devshell/commands.nix
+++ b/devshell/commands.nix
@@ -2,6 +2,11 @@
 let
   homeFlake = "$HOME/.config/home-manager/flake.nix";
   devKey = ".keys/dev.key";
+  sshMachine = pkgs.writeShellApplication {
+    name = "ssh-machine";
+    runtimeInputs = with pkgs; [ coreutils git jq openssh ];
+    text = builtins.readFile ./ssh-machine.sh;
+  };
 in
 {
   commands = [
@@ -52,20 +57,7 @@ in
       name = "ssh-machine";
       category = "utilities";
       help = "SSH to a machine by NixOS system or home-manager config name";
-      command = ''
-        name="$1"
-        shift
-        # Run from the project root so deploy's relative identity path (.keys/deploy.key) resolves
-        cd "$PRJ_ROOT"
-        # deploy-rs node names are the system/home name, with `@` mangled to `-at-`
-        node="''${name//@/-at-}"
-        # Single eval: resolve `user@host` plus merged (global + node) deploy-rs ssh options
-        info="$(nix eval --raw .#deploy --apply 'd: let n = d.nodes."'"$node"'"; in "''${n.sshUser}@''${n.hostname} ''${builtins.concatStringsSep " " (d.sshOpts ++ n.sshOpts)}"')"
-        target="''${info%% *}"
-        opts="''${info#* }"
-        # shellcheck disable=SC2086
-        exec ${pkgs.openssh}/bin/ssh $opts "$target" "$@"
-      '';
+      command = ''exec ${sshMachine}/bin/ssh-machine "$@"'';
     }
     {
       name = "json2nix";
diff --git a/devshell/ssh-machine.sh b/devshell/ssh-machine.sh
new file mode 100644
index 0000000..fc70a9f
--- /dev/null
+++ b/devshell/ssh-machine.sh
@@ -0,0 +1,74 @@
+set -euo pipefail
+
+refresh=false
+
+if [[ ${1:-} == --refresh ]]; then
+  refresh=true
+  shift
+fi
+
+if [[ $# == 0 && $refresh == false ]] || [[ ${1:-} == --help ]]; then
+  echo 'Usage: ssh-machine [--refresh] <name> [cmd ...]'
+  echo '       ssh-machine --refresh'
+  exit 0
+fi
+
+# Resolve deploy's relative identity path from the checkout root.
+cd "$PRJ_ROOT"
+
+cache_dir=.cache/ssh-machine
+cache=$cache_dir/connections.json
+
+fingerprint() {
+  {
+    git rev-parse HEAD &&
+    git diff --no-ext-diff --no-textconv --binary HEAD -- &&
+    git diff --no-ext-diff --no-textconv --binary --cached --
+  } | sha256sum | cut -d ' ' -f 1
+}
+
+key=$(fingerprint)
+
+if [[ $refresh == true ]] || ! jq -e --arg key "$key" \
+  '.fingerprint == $key and (.nodes | type == "object")' "$cache" >/dev/null 2>&1; then
+  mkdir -p "$cache_dir"
+  tmp=$(mktemp "$cache_dir/.connections.XXXXXXXX")
+  trap 'rm -f "$tmp"' EXIT
+
+  echo 'Refreshing ssh-machine connection cache…' >&2
+
+  # Interpolation here belongs to Nix, not the shell.
+  # shellcheck disable=SC2016
+  nix eval --json .#deploy --apply '
+    d: builtins.mapAttrs (_: n:
+      d.sshOpts ++ n.sshOpts ++ [ "${n.sshUser}@${n.hostname}" ]
+    ) d.nodes
+  ' > "$tmp"
+
+  if [[ $(fingerprint) != "$key" ]]; then
+    echo 'Checkout changed during evaluation; retry ssh-machine.' >&2
+    exit 1
+  fi
+
+  payload=$(jq -c --arg key "$key" '{fingerprint: $key, nodes: .}' "$tmp")
+  printf '%s\n' "$payload" > "$tmp"
+  mv -f "$tmp" "$cache"
+  trap - EXIT
+fi
+
+[[ $# -gt 0 ]] || exit 0
+
+name=$1
+shift
+
+# deploy-rs mangles home configuration names containing @.
+node=${name//@/-at-}
+
+args=$(jq -ce --arg node "$node" '
+  .nodes | if has($node) then .[$node]
+  else error("Unknown deploy node: " + $node) end
+' "$cache")
+
+mapfile -d '' -t ssh_args < <(jq -j '.[] | ., "\u0000"' <<< "$args")
+
+exec ssh "${ssh_args[@]}" "$@"
diff --git a/docs/deployment.md b/docs/deployment.md
index e47921f..1beb6e9 100644
--- a/docs/deployment.md
+++ b/docs/deployment.md
@@ -58,7 +58,16 @@ Generated profiles deploy in this order:
 
 `ssh-machine <name> [cmd]` resolves `user@host` and the merged global/node `sshOpts` from
 `.#deploy`, using the same `my.deploy.enable` gate and `@` → `-at-` mangling as `deploy`, then runs
-`ssh`. Boxes default to `fish`, so pipe multi-statement remote scripts through `bash`, for example
+`ssh`. Connection settings for all nodes are cached together in `.cache/ssh-machine/`;
+normal connections read the cache without running Nix. A fingerprint of Git HEAD and
+staged/unstaged tracked changes automatically invalidates it, including newly added files
+after `git add`.
+Untracked and ignored files do not affect the fingerprint. Any tracked edit, even an unrelated
+one, causes the next connection to refresh all nodes. Use `ssh-machine --refresh` to force a
+refresh, or `ssh-machine --refresh <name> [cmd]` to refresh and connect. Refresh failures stop
+the command; the previous cache is never used as a fallback.
+
+Boxes default to `fish`, so pipe multi-statement remote scripts through `bash`, for example
 `ssh-machine <name> bash -s < script.sh`. If a flaky agent stalls public-key authentication, use
 `SSH_AUTH_SOCK= ssh-machine …`.