diff --git a/tests/zsh/startup.bats b/tests/zsh/startup.bats
index f92c8862..5359132a 100644
--- a/tests/zsh/startup.bats
+++ b/tests/zsh/startup.bats
@@ -49,7 +49,7 @@ EOF
     XDG_CACHE_HOME="$TEST_HOME/.cache" \
     FPATH="$BATS_TEST_TMPDIR/functions" \
     PATH="$TEST_BIN:$PATH" \
-    zsh -dfi -c "source '$REPO_ROOT/zsh/.zshrc'"
+    zsh -dfi -c "source '$REPO_ROOT/zsh/.zshenv'; source '$REPO_ROOT/zsh/.zshrc'"
 
   [ "$status" -eq 0 ]
   grep -Fx -- "--quiet -S hl=herdr --session main" "$ABBR_LOG"
@@ -61,7 +61,7 @@ EOF
     XDG_CACHE_HOME="$TEST_HOME/.cache" \
     FPATH="$BATS_TEST_TMPDIR/functions" \
     PATH="$TEST_BIN:$PATH" \
-    zsh -dfi -c "source '$REPO_ROOT/zsh/.zshrc'"
+    zsh -dfi -c "source '$REPO_ROOT/zsh/.zshenv'; source '$REPO_ROOT/zsh/.zshrc'"
 
   [ "$status" -eq 0 ]
   grep -Fx -- \
@@ -75,7 +75,7 @@ EOF
     XDG_CACHE_HOME="$TEST_HOME/.cache" \
     FPATH="$BATS_TEST_TMPDIR/functions" \
     PATH="$TEST_BIN:$PATH" \
-    zsh -dfi -c "source '$REPO_ROOT/zsh/.zshrc'"
+    zsh -dfi -c "source '$REPO_ROOT/zsh/.zshenv'; source '$REPO_ROOT/zsh/.zshrc'"
 
   [ "$status" -eq 0 ]
   [ "$(cat "$COMPINIT_LOG")" = "-C -d $TEST_HOME/.cache/zsh/.zcompdump" ]
@@ -91,6 +91,154 @@ EOF
   ! [[ "$stderr" == *"brew shellenv"* ]]
 }
 
+@test "clean login startup orders Nix profiles and fallback tools before system entries" {
+  local _user_profile="$TEST_HOME/.nix-profile/bin"
+  local _per_user_profile="/etc/profiles/per-user/startup-test/bin"
+  local _system_profile="/run/current-system/sw/bin"
+  local _default_profile="/nix/var/nix/profiles/default/bin"
+
+  run_startup_path "$_user_profile:$_per_user_profile:$_system_profile:$_default_profile:/usr/bin:$TEST_BIN:/bin" -lic
+
+  [ "$status" -eq 0 ]
+  local _expected=(
+    "$_user_profile"
+    "$_per_user_profile"
+    "$_system_profile"
+    "$_default_profile"
+    "$TEST_HOME/.local/bin"
+    "$TEST_HOME/.cargo/bin"
+    "$TEST_HOME/.gem/bin"
+    /opt/homebrew/bin
+    /Library/TeX/texbin
+    /usr/bin
+    "$TEST_BIN"
+    /bin
+    /Applications/Obsidian.app/Contents/MacOS
+  )
+  [ "${#lines[@]}" -eq "${#_expected[@]}" ]
+  local _index
+  for _index in "${!_expected[@]}"; do
+    [ "${lines[_index]}" = "${_expected[_index]}" ] || {
+      printf 'unexpected PATH entry at %s: %s\n' "$_index" "$output" >&2
+      return 1
+    }
+  done
+}
+
+@test "startup preserves inherited devShell PATH order in all shell modes" {
+  local _inherited="/nix/store/devshell-tools/bin:/workspace/project/bin:$TEST_HOME/.cargo/bin:/opt/homebrew/bin:$TEST_HOME/.nix-profile/bin:/usr/bin:$TEST_HOME/.local/bin:/Library/TeX/texbin:$TEST_BIN:/bin"
+  local _mode
+  for _mode in -c -ic -lic; do
+    run_startup_path "$_inherited:$_inherited" "$_mode"
+
+    [ "$status" -eq 0 ]
+    local _expected=(
+      /nix/store/devshell-tools/bin
+      /workspace/project/bin
+      "$TEST_HOME/.cargo/bin"
+      /opt/homebrew/bin
+      "$TEST_HOME/.nix-profile/bin"
+      "$TEST_HOME/.gem/bin"
+      /usr/bin
+      "$TEST_HOME/.local/bin"
+      /Library/TeX/texbin
+      "$TEST_BIN"
+      /bin
+    )
+    if [ "$_mode" = -lic ]; then
+      _expected+=(/Applications/Obsidian.app/Contents/MacOS)
+    fi
+    [ "${#lines[@]}" -eq "${#_expected[@]}" ]
+    local _index
+    for _index in "${!_expected[@]}"; do
+      [ "${lines[_index]}" = "${_expected[_index]}" ] || {
+        printf 'unexpected PATH entry in %s at %s: %s\n' "$_mode" "$_index" "$output" >&2
+        return 1
+      }
+    done
+  done
+}
+
+@test "startup inserts missing fallback tools after inherited devShell entries in all shell modes" {
+  local _inherited="/nix/store/devshell-tools/bin:/workspace/project/bin:$TEST_BIN"
+  local _mode
+  for _mode in -c -ic -lic; do
+    run_startup_path "$_inherited:/usr/bin:/bin" "$_mode"
+
+    [ "$status" -eq 0 ]
+    local _expected=(
+      /nix/store/devshell-tools/bin
+      /workspace/project/bin
+      "$TEST_BIN"
+      "$TEST_HOME/.local/bin"
+      "$TEST_HOME/.cargo/bin"
+      "$TEST_HOME/.gem/bin"
+    )
+    if [ "$_mode" != -c ]; then
+      _expected+=(/opt/homebrew/bin /Library/TeX/texbin)
+    fi
+    _expected+=(/usr/bin /bin)
+    if [ "$_mode" = -lic ]; then
+      _expected+=(/Applications/Obsidian.app/Contents/MacOS)
+    fi
+    [ "$output" = "$(printf '%s\n' "${_expected[@]}")" ] || {
+      printf 'unexpected PATH in %s: %s\n' "$_mode" "$output" >&2
+      return 1
+    }
+  done
+}
+
+@test "startup inserts before the first system entry or appends when none exists" {
+  local _system
+  for _system in /usr/local/bin /usr/bin /bin /usr/sbin /sbin ''; do
+    local _inherited="$TEST_BIN"
+    local _expected=(
+      "$TEST_BIN"
+      "$TEST_HOME/.local/bin"
+      "$TEST_HOME/.cargo/bin"
+      "$TEST_HOME/.gem/bin"
+    )
+    if [ -n "$_system" ]; then
+      _inherited+=":$_system:/custom/bin:/usr/bin"
+      _expected+=("$_system" /custom/bin)
+      if [ "$_system" != /usr/bin ]; then
+        _expected+=(/usr/bin)
+      fi
+    fi
+    run_startup_path "$_inherited" -c
+
+    [ "$status" -eq 0 ]
+    [ "$output" = "$(printf '%s\n' "${_expected[@]}")" ] || {
+      printf 'unexpected PATH for system entry %s: %s\n' "$_system" "$output" >&2
+      return 1
+    }
+  done
+}
+
+run_startup_path() {
+  # Source repository files explicitly to isolate host startup configuration.
+  run --separate-stderr env -i \
+    HOME="$TEST_HOME" \
+    USER=startup-test \
+    XDG_CACHE_HOME="$TEST_HOME/.cache" \
+    FPATH="$BATS_TEST_TMPDIR/functions" \
+    COMPINIT_LOG="$COMPINIT_LOG" \
+    ABBR_LOG="$ABBR_LOG" \
+    REPO_ROOT="$REPO_ROOT" \
+    PATH="$1" \
+    "$(command -v zsh)" -df "$2" '
+      source "$REPO_ROOT/zsh/.zshenv"
+      source "$REPO_ROOT/zsh/.zshenv"
+      if [[ -o login ]]; then
+        source "$REPO_ROOT/zsh/.zprofile"
+      fi
+      if [[ -o interactive ]]; then
+        source "$REPO_ROOT/zsh/.zshrc"
+      fi
+      print -rl -- "${path[@]}"
+    '
+}
+
 @test "Home Manager activation invokes the packaged Zsh cache builder" {
   run --separate-stderr nix build --no-link --print-out-paths \
     "$TEST_FLAKE#homeConfigurations.\"kaito@mbp\".activationPackage"
diff --git a/zsh/.zprofile b/zsh/.zprofile
index f306f628..8ac53fb9 100644
--- a/zsh/.zprofile
+++ b/zsh/.zprofile
@@ -1,7 +1,5 @@
-export PATH="$HOME/.local/bin:$PATH"
-
 # Added by OrbStack: command-line tools and integration
 source ~/.orbstack/shell/init.zsh 2>/dev/null || :
 
 # Added by Obsidian
-export PATH="$PATH:/Applications/Obsidian.app/Contents/MacOS"
+path+=(/Applications/Obsidian.app/Contents/MacOS)
diff --git a/zsh/.zshenv b/zsh/.zshenv
index 18efee13..3f720c4c 100644
--- a/zsh/.zshenv
+++ b/zsh/.zshenv
@@ -1,4 +1,22 @@
-export PATH=$HOME/.gem/bin:$HOME/.cargo/bin:$PATH
+# Preserve inherited tool precedence and keep each entry only once.
+typeset -U path PATH
+function _insert_fallback_paths() {
+  local -a _missing
+  local _entry _index=1
+  for _entry in "$@"; do
+    (( ${path[(Ie)$_entry]} )) || _missing+=("$_entry")
+  done
+  (( ${#_missing} )) || return 0
+  for _entry in "${path[@]}"; do
+    case "$_entry" in
+      /usr/local/bin|/usr/bin|/bin|/usr/sbin|/sbin) break ;;
+    esac
+    (( _index++ ))
+  done
+  path=("${(@)path[1,_index-1]}" "${_missing[@]}" "${(@)path[_index,-1]}")
+}
+
+_insert_fallback_paths "$HOME/.local/bin" "$HOME/.cargo/bin" "$HOME/.gem/bin"
 # Enforced on every zsh start so stale inherited environments
 # (e.g. a long-running herdr server snapshot) cannot override it.
 export EDITOR=nvim
diff --git a/zsh/.zshrc b/zsh/.zshrc
index 370e3bd8..4576ae7b 100644
--- a/zsh/.zshrc
+++ b/zsh/.zshrc
@@ -10,6 +10,9 @@ if [[ "$OSTYPE" == darwin* && -z "${SSH_AUTH_SOCK:-}" ]]; then
   }
 fi
 
+# Global tools remain fallbacks without changing inherited tool precedence.
+_insert_fallback_paths /opt/homebrew/bin /Library/TeX/texbin
+
 # Completion
 ZSH_COMPDUMP="${XDG_CACHE_HOME:-$HOME/.cache}/zsh/.zcompdump"
 autoload -Uz compinit
@@ -75,11 +78,7 @@ function command_not_found_handler() {
 
 DOTFILES="$HOME/ghq/github.com/furedea/dotfiles"
 
-export PATH="/usr/bin:$PATH"
-export PATH="/opt/homebrew/bin:$PATH"
 export XDG_CONFIG_HOME="$HOME/.config"
-export PATH="/Library/TeX/texbin:$PATH"
-export PATH="$HOME/.local/bin:$PATH"
 
 # Plugins
 source "$XDG_CONFIG_HOME/zsh/nix-plugins.zsh"