diff --git a/bin/omarchy-install-hermes-cli b/bin/omarchy-install-hermes-cli
index 4a6923a3..35405269 100755
--- a/bin/omarchy-install-hermes-cli
+++ b/bin/omarchy-install-hermes-cli
@@ -88,21 +88,27 @@ hermes_runs() {
     timeout 15 "$HOME/.local/bin/hermes" --version >/dev/null 2>&1
 }
 
+# A flag counts only when the help defines it, not whenever it is mentioned:
+# what follows must be a shape argparse prints after a definition -- the usage
+# line's closing bracket, the gap before same-line help text, an uppercase
+# metavar, or the end of the line. Prose like "With --tui: run ..." stays
+# prose, and --tui-theme or --tui_mode never answers for --tui. Not probed by
+# parsing an actual invocation on purpose: a release that ignores unknown
+# arguments would turn the probe into a live session.
+help_defines_flag() {
+  grep -qE -- "$1(]|[[:space:]][[:upper:]]|[[:space:]]{2}|$)" <<<"$2"
+}
+
 # Probed for the flags omarchy-agent actually passes -- --query to seed the
 # session and --tui to keep it interactive -- rather than a flag that merely
 # shipped alongside them: the previous marker, --oneshot, was dropped in Hermes
 # v0.20 and left working installs stranded as "not ready".
-#
-# Matched at a flag boundary, not as a substring: a bare grep for --tui also
-# accepts a release that lists only --tui-theme while having dropped --tui
-# itself, which would call an install ready that omarchy-agent cannot drive --
-# the same false verdict this check exists to prevent, merely inverted.
 hermes_prompt_ready() {
   local help
   hermes_runs &&
     help=$(timeout 15 "$HOME/.local/bin/hermes" chat --help 2>/dev/null) &&
-    grep -qE -- '--tui([^[:alnum:]_-]|$)' <<<"$help" &&
-    grep -qE -- '--query([^[:alnum:]_-]|$)' <<<"$help"
+    help_defines_flag '--tui' "$help" &&
+    help_defines_flag '--query' "$help"
 }
 
 # --owns answers whether the wrapper on PATH is the one this command wrote, so
@@ -127,7 +133,17 @@ if [[ $mode == "--remove" ]]; then
   if ours; then
     mise rm -g "$tool" >/dev/null 2>&1 || true
     mise uninstall --all "$tool" >/dev/null 2>&1 || true
-    rm -f "$HOME/.local/bin/hermes"
+    rm -f "$HOME/.local/bin/hermes" 2>/dev/null || true
+
+    # Every step is attempted before any is judged, and judged by what is left
+    # rather than by what the commands claimed: the marked stub still answering
+    # hermes, or mise still resolving the tool, is a CLI still installed no
+    # matter how the removal exited.
+    if ours || mise where "$tool" >/dev/null 2>&1; then
+      echo "Could not remove the Hermes CLI Omarchy installed." >&2
+      echo "Remove ~/.local/bin/hermes and the mise tool '$tool', then run omarchy-install-hermes-cli --remove again." >&2
+      exit 1
+    fi
   fi
 
   exit 0
diff --git a/bin/omarchy-remove-ai-hermes b/bin/omarchy-remove-ai-hermes
index f332dc4b..1145fbd1 100755
--- a/bin/omarchy-remove-ai-hermes
+++ b/bin/omarchy-remove-ai-hermes
@@ -13,7 +13,10 @@ omarchy-pkg-drop hermes-desktop
 # the app never superseded -- an interrupted install, or the terminal CLI from
 # before the app existed. Remove Hermes clears that too, scoped by the installer
 # to what Omarchy owns so a hermes the user set up themselves is left alone.
-omarchy-install-hermes-cli --remove
+# Tolerated here rather than fatal, so the ~/.hermes handling below still runs;
+# the failure is answered for at the end instead of being swallowed.
+cli_removed=true
+omarchy-install-hermes-cli --remove || cli_removed=false
 
 # The app writes this when the runtime it provisions under ~/.hermes has landed,
 # and it is the only thing that tells that runtime apart from one the user
@@ -64,3 +67,9 @@ else
   echo "Hermes Desktop has been removed."
   echo "It never finished installing its own Hermes, so nothing in ~/.hermes was touched."
 fi
+
+# The messages above still hold -- the app and its runtime are gone -- but a CLI
+# teardown that failed already said so on stderr, and that stands.
+if [[ $cli_removed == "false" ]]; then
+  exit 1
+fi
diff --git a/test/shell.d/hermes-cli-test.sh b/test/shell.d/hermes-cli-test.sh
index 69a52f61..24f8e8bc 100755
--- a/test/shell.d/hermes-cli-test.sh
+++ b/test/shell.d/hermes-cli-test.sh
@@ -430,12 +430,19 @@ pass "--remove is idempotent when no Hermes CLI is present"
 printf '%s\n' "#!/bin/bash" "$stub_marker" >"$remove_home/.local/bin/hermes"
 chmod +x "$remove_home/.local/bin/hermes"
 : >"$mise_log"
-OMARCHY_TEST_MISE_WHERE_OK=1 run_remove || fail "--remove succeeds tearing down an owned CLI"
+run_remove || fail "--remove succeeds tearing down an owned CLI"
 tr '\0' '\n' <"$mise_log" | grep -q '^rm$' || fail "--remove drops the mise tool from config"
 tr '\0' '\n' <"$mise_log" | grep -q '^uninstall$' || fail "--remove uninstalls the mise tool"
 [[ ! -e $remove_home/.local/bin/hermes ]] || fail "--remove takes the stub it owns"
 pass "--remove tears down the mise CLI and the stub this installer owns"
 
+# When mise still resolves the tool after the teardown, the environment
+# survived whatever uninstall claimed, and --remove has to say so.
+printf '%s\n' "#!/bin/bash" "$stub_marker" >"$remove_home/.local/bin/hermes"
+chmod +x "$remove_home/.local/bin/hermes"
+OMARCHY_TEST_MISE_WHERE_OK=1 run_remove && fail "--remove claims success while mise still resolves the tool"
+pass "--remove fails when the mise environment survives the teardown"
+
 foreign_remove_body="#!/bin/bash
 exec /usr/local/bin/my-own-hermes \"\$@\""
 printf '%s\n' "$foreign_remove_body" >"$remove_home/.local/bin/hermes"
@@ -450,6 +457,16 @@ tr '\0' '\n' <"$mise_log" | grep -Eq '^(rm|uninstall)$' &&
   fail "--remove never removes a mise environment it cannot prove is Omarchy's"
 pass "--remove leaves a Hermes the user installed themselves"
 
+# Judged by what is left, not by what rm claimed: a stub that survives the
+# teardown is a CLI still installed, and --remove has to say so.
+printf '%s\n' "#!/bin/bash" "$stub_marker" >"$remove_home/.local/bin/hermes"
+chmod +x "$remove_home/.local/bin/hermes"
+chmod 555 "$remove_home/.local/bin"
+run_remove && fail "--remove claims success while the stub survives"
+chmod 755 "$remove_home/.local/bin"
+rm -f "$remove_home/.local/bin/hermes"
+pass "--remove fails when the stub cannot be removed"
+
 # The app's marker says its install once landed, not that it is still there. A
 # wrapper whose runtime has since gone answers for nothing, so readiness runs
 # the command, exactly as it does for a hermes the user installed themselves.
@@ -541,3 +558,19 @@ SH
 chmod +x "$ready_home/.hermes/hermes-agent/venv/bin/hermes"
 run_ready_check && fail "--check accepts flags that extend --tui/--query with an underscore"
 pass "an underscore continuation is not the bare flag"
+
+# A flag mentioned in another option's help text is not that option. Hermes
+# already writes "With --tui:" into --dev's description, so prose has to stay
+# prose even when both names appear in it.
+cat >"$ready_home/.hermes/hermes-agent/venv/bin/hermes" <<'SH'
+#!/bin/bash
+if [[ ${1:-} == "chat" && ${2:-} == "--help" ]]; then
+  echo "  --dev                 With --tui: run sources via tsx"
+  echo "  --log FILE            Where --query output lands"
+else
+  echo "hermes-agent 0.0.0-test"
+fi
+SH
+chmod +x "$ready_home/.hermes/hermes-agent/venv/bin/hermes"
+run_ready_check && fail "--check accepts flags that appear only in option descriptions"
+pass "a flag mentioned in prose is not a defined option"
diff --git a/test/shell.d/hermes-remove-test.sh b/test/shell.d/hermes-remove-test.sh
index 6045c9a1..d3389087 100755
--- a/test/shell.d/hermes-remove-test.sh
+++ b/test/shell.d/hermes-remove-test.sh
@@ -22,6 +22,7 @@ SH
 cat >"$mock_bin/omarchy-install-hermes-cli" <<'SH'
 #!/bin/bash
 printf '%s\0' "$@" >>"$OMARCHY_TEST_INSTALLER_LOG"
+exit "${OMARCHY_TEST_INSTALLER_STATUS:-0}"
 SH
 chmod +x "$mock_bin"/*
 
@@ -46,6 +47,7 @@ remove() {
   : >"$test_tmp/installer-log"
   OMARCHY_TEST_DROP_LOG="$test_tmp/drop-log" \
     OMARCHY_TEST_INSTALLER_LOG="$test_tmp/installer-log" \
+    OMARCHY_TEST_INSTALLER_STATUS="${OMARCHY_TEST_INSTALLER_STATUS:-0}" \
     HOME="$test_home" PATH="$mock_bin:$PATH" \
     bash "$ROOT/bin/omarchy-remove-ai-hermes" >/dev/null 2>&1
 }
@@ -131,3 +133,14 @@ remove || fail "remove succeeds with a wrapper pointing at a sibling directory"
 [[ -f $test_home/.local/bin/hermes && $(cat "$test_home/.local/bin/hermes") == "$sibling_body" ]] ||
   fail "a wrapper pointing at ~/xhermes is not mistaken for one pointing into ~/.hermes"
 pass "removal matches the runtime path as a plain string"
+
+# A CLI teardown that fails must not stop the runtime handling, and must not be
+# papered over either: the data work still happens, and the failure reaches the
+# caller's exit code.
+seed_install
+printf '%s\n' "#!/bin/bash" "exec $test_home/.hermes/hermes-agent/venv/bin/hermes \"\$@\"" \
+  >"$test_home/.local/bin/hermes"
+OMARCHY_TEST_INSTALLER_STATUS=1 remove && fail "a failed CLI teardown surfaces in the exit code"
+[[ ! -d $test_home/.hermes/hermes-agent ]] ||
+  fail "a failed CLI teardown does not stop the runtime removal"
+pass "a failed CLI teardown is reported after the runtime is handled"