diff --git a/CHANGELOG.md b/CHANGELOG.md
index a4036ef..23fab35 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -7,6 +7,13 @@ and versions are tracked in the repo-root `VERSION` file.
 
 ## [Unreleased]
 
+### Fixed
+
+- Hardened `std_run --timeout` retry internals so timeout discovery is cached
+  per call, fallback setup failures return a generic error, and fallback timer
+  cleanup cannot remove the timeout marker before it is observed.
+- Clarified `update_file_section` logging when appending a new managed section.
+
 ### Removed
 
 - Removed early compatibility aliases `run`, `std_run_with_timeout`, and
diff --git a/lib/bash/file/lib_file.sh b/lib/bash/file/lib_file.sh
index 0f5d750..6757bef 100644
--- a/lib/bash/file/lib_file.sh
+++ b/lib/bash/file/lib_file.sh
@@ -240,7 +240,11 @@ update_file_section() {
         __file_remove_temp_paths__ "$current_content_file"
     fi
 
-    log_info "Updating '$target_file'"
+    if [[ "$section_exists" == true ]]; then
+        log_info "Updating '$target_file'"
+    else
+        log_info "Adding section to '$target_file'"
+    fi
     if ! __file_make_target_temp__ temp_file "$target_file"; then
         log_error "Failed to create temporary file for '$target_file'."
         __file_remove_temp_paths__ "$new_content_file"
diff --git a/lib/bash/file/tests/lib_file.bats b/lib/bash/file/tests/lib_file.bats
index 8464b4e..4e404a3 100644
--- a/lib/bash/file/tests/lib_file.bats
+++ b/lib/bash/file/tests/lib_file.bats
@@ -33,6 +33,26 @@ file_mode() {
     [ "$(cat "$target")" = $'line-one\n# BEGIN\nfirst\nsecond\n# END' ]
 }
 
+@test "update_file_section logs adding when markers are absent" {
+    local script="$TEST_TMPDIR/add-log.sh"
+    local target="$TEST_TMPDIR/config.txt"
+    cat > "$script" <<EOF
+#!/usr/bin/env bash
+source "$BASE_BASH_DIR/std/lib_std.sh"
+source "$BASE_BASH_DIR/file/lib_file.sh"
+printf 'line-one' > "\$1"
+update_file_section "\$1" "# BEGIN" "# END" "first"
+EOF
+    chmod +x "$script"
+
+    bats_run bash "$script" "$target"
+
+    [ "$status" -eq 0 ]
+    [[ "$output" == *"Adding section to '$target'"* ]]
+    [[ "$output" != *"Updating '$target'"* ]]
+    [ "$(cat "$target")" = $'line-one\n# BEGIN\nfirst\n# END' ]
+}
+
 @test "update_file_section appends to an empty file without a leading blank line" {
     local target="$TEST_TMPDIR/config.txt"
     touch "$target"
diff --git a/lib/bash/std/lib_std.sh b/lib/bash/std/lib_std.sh
index 67d3d1c..04ac4ed 100644
--- a/lib/bash/std/lib_std.sh
+++ b/lib/bash/std/lib_std.sh
@@ -799,12 +799,11 @@ __std_join_run_policy__() {
 }
 
 __std_run_once__() {
-    local timeout_seconds="$1"
-    shift
-    local timeout_path=""
+    local timeout_seconds="$1" timeout_path="$2"
+    shift 2
 
     if [[ -n "$timeout_seconds" ]]; then
-        if std_command_path timeout_path timeout || std_command_path timeout_path gtimeout; then
+        if [[ -n "$timeout_path" ]]; then
             "$timeout_path" "$timeout_seconds" "$@"
         else
             __std_run_with_timeout_fallback__ "$timeout_seconds" "$@"
@@ -885,7 +884,7 @@ __std_run_status_message__() {
 __std_run_impl__() {
     local helper_name="$1"
     shift
-    local exit_on_failure=1 quiet=0 timeout_seconds="" max_attempts=1 retry_delay=0
+    local exit_on_failure=1 quiet=0 timeout_seconds="" timeout_path="" max_attempts=1 retry_delay=0
 
     # Parse optional run flags before the command.
     while (($#)); do
@@ -969,9 +968,13 @@ __std_run_impl__() {
     # Execute the command. Using "$@" is the key. It expands each argument
     # as a separate, quoted string, preserving spaces and special characters.
     # This is the safe, modern alternative to using `eval`.
+    if [[ -n "$timeout_seconds" ]]; then
+        std_command_path timeout_path timeout || std_command_path timeout_path gtimeout || timeout_path=""
+    fi
+
     local attempt=1 exit_code=0 message
     while ((attempt <= max_attempts)); do
-        if __std_run_once__ "$timeout_seconds" "$@"; then
+        if __std_run_once__ "$timeout_seconds" "$timeout_path" "$@"; then
             return 0
         else
             exit_code=$?
@@ -1031,7 +1034,7 @@ __std_run_with_timeout_fallback__() {
     local timeout_marker command_pid timer_pid command_status
     local kill_grace_seconds=1
 
-    std_make_temp_file timeout_marker base-bash-libs-timeout || return 127
+    std_make_temp_file timeout_marker base-bash-libs-timeout || return 1
 
     "$@" &
     command_pid=$!
@@ -1049,7 +1052,7 @@ __std_run_with_timeout_fallback__() {
     command_status=$?
 
     if kill -0 "$timer_pid" 2>/dev/null; then
-        kill "$timer_pid" 2>/dev/null || true
+        kill -KILL "$timer_pid" 2>/dev/null || true
     fi
     wait "$timer_pid" 2>/dev/null || true
 
diff --git a/lib/bash/std/tests/lib_std.bats b/lib/bash/std/tests/lib_std.bats
index 9304c9a..a0a427e 100644
--- a/lib/bash/std/tests/lib_std.bats
+++ b/lib/bash/std/tests/lib_std.bats
@@ -974,16 +974,25 @@ EOF
 }
 
 @test "std_run --timeout returns 124 when the command times out" {
+    local script="$TEST_TMPDIR/run-timeout.sh"
     local stderr_file="$TEST_TMPDIR/run-timeout.err"
-    local rc
+    local rc_file="$TEST_TMPDIR/run-timeout.rc"
 
-    if std_run --no-exit --quiet --timeout 1 sleep 2 2>"$stderr_file"; then
-        rc=0
-    else
-        rc=$?
-    fi
+    create_script "$script" <<EOF
+#!/usr/bin/env bash
+source "$STDLIB_PATH"
+if std_run --no-exit --quiet --timeout 1 /bin/sleep 2 2>"$stderr_file"; then
+    printf '0\n' > "$rc_file"
+else
+    printf '%s\n' "\$?" > "$rc_file"
+fi
+EOF
 
-    [ "$rc" -eq 124 ]
+    bats_run bash "$script"
+
+    [ "$status" -eq 0 ]
+    [ "$output" = "" ]
+    [ "$(cat "$rc_file")" = "124" ]
     [ ! -s "$stderr_file" ]
 }
 
@@ -1086,6 +1095,95 @@ EOF
     [ "$(cat "$output_file")" = "ok" ]
 }
 
+@test "std_run discovers timeout binary once across retries" {
+    local fake_bin="$TEST_TMPDIR/timeout-bin"
+    local lookup_file="$TEST_TMPDIR/timeout-lookups.txt"
+    local counter_file="$TEST_TMPDIR/timeout-discovery-count.txt"
+    local script="$TEST_TMPDIR/timeout-discovery-command.sh"
+    local rc
+    local -a lookups=()
+
+    mkdir -p "$fake_bin"
+    create_script "$fake_bin/timeout" <<'EOF'
+#!/usr/bin/env bash
+shift
+"$@"
+EOF
+    create_script "$script" <<'EOF'
+#!/usr/bin/env bash
+count=0
+[[ -f "$1" ]] && count="$(cat "$1")"
+count=$((count + 1))
+printf '%s\n' "$count" > "$1"
+((count >= 3))
+EOF
+
+    eval "$(declare -f std_command_path | sed '1s/std_command_path/__orig_std_command_path/')"
+    std_command_path() {
+        if [[ "${2-}" == "timeout" || "${2-}" == "gtimeout" ]]; then
+            printf '%s\n' "$2" >> "$lookup_file"
+        fi
+        __orig_std_command_path "$@"
+    }
+
+    PATH="$fake_bin:$PATH" std_run --no-exit --quiet --timeout 5 --max-attempts 3 /bin/bash "$script" "$counter_file"
+    rc=$?
+    unset -f std_command_path __orig_std_command_path
+
+    [ "$rc" -eq 0 ]
+    mapfile -t lookups < "$lookup_file"
+    [ "${#lookups[@]}" -eq 1 ]
+    [ "${lookups[0]}" = "timeout" ]
+    [ "$(cat "$counter_file")" = "3" ]
+}
+
+@test "std_run fallback timeout returns 1 when marker creation fails" {
+    local fake_bin="$TEST_TMPDIR/no-timeout-bin"
+    local stderr_file="$TEST_TMPDIR/timeout-marker-failure.err"
+    local rc
+
+    mkdir -p "$fake_bin"
+
+    eval "$(declare -f std_make_temp_file | sed '1s/std_make_temp_file/__orig_std_make_temp_file/')"
+    std_make_temp_file() {
+        return 1
+    }
+
+    if PATH="$fake_bin" std_run --no-exit --quiet --timeout 5 /bin/echo fallback 2>"$stderr_file"; then
+        rc=0
+    else
+        rc=$?
+    fi
+    unset -f std_make_temp_file __orig_std_make_temp_file
+
+    [ "$rc" -eq 1 ]
+}
+
+@test "std_run fallback timeout kills timer with SIGKILL after command exits" {
+    local fake_bin="$TEST_TMPDIR/no-timeout-bin"
+    local kill_log="$TEST_TMPDIR/timeout-kill.log"
+    local output_file="$TEST_TMPDIR/timeout-kill-output.txt"
+    local rc
+
+    mkdir -p "$fake_bin"
+    ln -s "$(command -v mktemp)" "$fake_bin/mktemp"
+    ln -s "$(command -v rm)" "$fake_bin/rm"
+    ln -s "$(command -v sleep)" "$fake_bin/sleep"
+
+    kill() {
+        printf '%s\n' "$*" >> "$kill_log"
+        builtin kill "$@"
+    }
+
+    PATH="$fake_bin" std_run --no-exit --quiet --timeout 5 /bin/echo fallback > "$output_file"
+    rc=$?
+    unset -f kill
+
+    [ "$rc" -eq 0 ]
+    [ "$(cat "$output_file")" = "fallback" ]
+    [[ "$(cat "$kill_log")" == *"-KILL "* ]]
+}
+
 @test "std_run rejects invalid execution policy options" {
     local stderr_file="$TEST_TMPDIR/run-policy-invalid.err"
     local rc