diff --git a/ROADMAP.md b/ROADMAP.md
index a748325f..ee19ca54 100644
--- a/ROADMAP.md
+++ b/ROADMAP.md
@@ -2188,7 +2188,7 @@ ear], /color [scheme], /effort [low|medium|high], /fast, /summary, /tag [label],
 
    **Source.** Jobdori dogfood 2026-04-18 against `/tmp/cdK` on main HEAD `8db8e49` in response to Clawhip pinpoint nudge at `1494751832399024178`. A partial regression of ROADMAP #39 / #54 — the filter was applied to the primary slash-command listing and to REPL completions, but the `--help` Resume-safe one-liner was overlooked. New stubs added to `STUB_COMMANDS` since those filings keep propagating to this section. Sibling to #78 (`claw plugins` CLI route wired but never constructed): both are "surface advertises something that doesn't work at runtime" gaps in `--help` / parser coverage. Distinct from the truth-audit / discovery-overreach / reporting-surface clusters — this is a self-contradicting help surface, not a runtime-state or config-hygiene bug.
 
-97. **`--allowedTools ""` and `--allowedTools ",,"` silently yield an empty allow-set that blocks every tool, with no error, no warning, and no trace of the active tool-restriction anywhere in `claw status` / `claw doctor` / `claw --output-format json` surfaces — compounded by `allowedTools` being a *rejected unknown key* in `.claw.json`, so there is no machine-readable way to inspect or recover what the current active allow-set actually is** — dogfooded 2026-04-18 on main HEAD `3ab920a` from `/tmp/cdL`. `--allowedTools "nonsense"` correctly returns a structured error naming every valid tool. `--allowedTools ""` silently produces `Some(BTreeSet::new())` and all subsequent tool lookups fail `contains()` because the set is empty. Neither `status` JSON nor `doctor` JSON exposes `allowed_tools`, so a claw that accidentally restricted itself to zero tools has no observable signal to recover from.
+97. **DONE — `--allowedTools ""` and `--allowedTools ",,"` silently yield an empty allow-set that blocks every tool, with no error, no warning, and no trace of the active tool-restriction anywhere in `claw status` / `claw doctor` / `claw --output-format json` surfaces — compounded by `allowedTools` being a *rejected unknown key* in `.claw.json`, so there is no machine-readable way to inspect or recover what the current active allow-set actually is** — dogfooded 2026-04-18 on main HEAD `3ab920a` from `/tmp/cdL`. `--allowedTools "nonsense"` correctly returns a structured error naming every valid tool. `--allowedTools ""` silently produces `Some(BTreeSet::new())` and all subsequent tool lookups fail `contains()` because the set is empty. Neither `status` JSON nor `doctor` JSON exposes `allowed_tools`, so a claw that accidentally restricted itself to zero tools has no observable signal to recover from.
 
     **Concrete repro.**
     ```
diff --git a/rust/crates/rusty-claude-cli/src/main.rs b/rust/crates/rusty-claude-cli/src/main.rs
index 6a3640a9..cc2021c1 100644
--- a/rust/crates/rusty-claude-cli/src/main.rs
+++ b/rust/crates/rusty-claude-cli/src/main.rs
@@ -3131,6 +3131,17 @@ fn parse_system_prompt_args(
                     "missing_flag_value: missing value for --cwd.\nUsage: --cwd <path>".to_string()
                 })?;
                 cwd = PathBuf::from(value);
+                // #99: validate --cwd path exists and is a directory
+                if !cwd.exists() {
+                    return Err(format!(
+                        "invalid_cwd: path '{value}' does not exist.\nUsage: claw system-prompt --cwd <existing-directory>"
+                    ));
+                }
+                if !cwd.is_dir() {
+                    return Err(format!(
+                        "invalid_cwd: path '{value}' is not a directory.\nUsage: claw system-prompt --cwd <existing-directory>"
+                    ));
+                }
                 index += 2;
             }
             "--date" => {
@@ -3138,9 +3149,22 @@ fn parse_system_prompt_args(
                     "missing_flag_value: missing value for --date.\nUsage: --date <YYYY-MM-DD>"
                         .to_string()
                 })?;
+                // #99: validate --date is a plausible date string (no newlines, reasonable length)
+                if value.contains('\n') || value.contains('\r') {
+                    return Err(format!(
+                        "invalid_flag_value: --date value contains invalid characters.\nUsage: --date <YYYY-MM-DD>"
+                    ));
+                }
+                if value.len() > 20 {
+                    return Err(format!(
+                        "invalid_flag_value: --date value is too long ({len} chars, expected YYYY-MM-DD).\nUsage: --date <YYYY-MM-DD>",
+                        len = value.len()
+                    ));
+                }
                 date.clone_from(value);
                 index += 2;
             }
+
             other => {
                 // #152: hint `--output-format json` when user types `--json`.
                 // #790: use unknown_option: prefix + \n hint so classify_error_kind returns