diff --git a/CHANGELOG.md b/CHANGELOG.md
index cc2e71b..c2a9eb4 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -5,6 +5,7 @@ All notable changes to ShellClaw are documented here. Format follows [Keep a Cha
 ## [Unreleased]
 
 ### Fixed
+- Unsandboxed `shell` no longer blocks forever in `waitpid` after the output cap fills; leftover children (including background grandchildren) are SIGKILL'd via the command process group, and truncated capture is NUL-terminated (#69).
 - `write_file` maps to the intended path instead of the first existing ancestor, so a nested path cannot truncate a workspace file treated as a directory or overwrite a same-named file in a parent (#67). Leaf workspace symlinks (dangling or an in-workspace alias) are rejected (`lstat` + `O_NOFOLLOW`) instead of creating host files outside the workspace (#90).
 - `write_file` persists via unique temp (`mkstemp`)+fsync+rename so a failed write cannot wipe an existing workspace file and a sibling `path.tmp` is not truncated (#78).
 - Camera capture fails closed when `workspace_only` is on with an empty `workspace_path`, and rejects leaf symlink outputs (#91, #90).
diff --git a/src/tools/shell.c b/src/tools/shell.c
index 89f125d..5638e59 100644
--- a/src/tools/shell.c
+++ b/src/tools/shell.c
@@ -19,12 +19,14 @@
 #include "sandbox/sandbox.h"
 #include "sandbox/allowlist.h"
 #include "cJSON.h"
+#include <errno.h>
 #include <poll.h>
 #include <signal.h>
 #include <stdio.h>
 #include <stdlib.h>
 #include <string.h>
 #include <sys/wait.h>
+#include <time.h>
 #include <unistd.h>
 
 #define DEFAULT_TIMEOUT_SEC 60
@@ -56,6 +58,50 @@ static int fallback_is_blocked(const char *cmd)
 
 static const config_t *g_shell_cfg;
 
+static void kill_command_tree(pid_t pid)
+{
+	if (kill(-pid, SIGKILL) != 0)
+		(void)kill(pid, SIGKILL);
+}
+
+/* Always SIGKILL the process group first so background grandchildren cannot
+ * leak after the shell has already exited (SIGPIPE, or `cmd &`). Then reap
+ * the tracked pid. Matching the hang fix for #69 / #96. */
+static int reap_running_child(pid_t pid)
+{
+	int status = 0;
+	int wr;
+	int retries;
+	struct timespec ts;
+	kill_command_tree(pid);
+	wr = waitpid(pid, &status, WNOHANG);
+	if (wr != 0)
+		return 0;
+	for (retries = 0; retries < 40; retries++) {
+		wr = waitpid(pid, &status, WNOHANG);
+		if (wr != 0)
+			return 1;
+		ts.tv_sec = 0;
+		ts.tv_nsec = 50 * 1000 * 1000;
+		(void)nanosleep(&ts, NULL);
+	}
+	(void)waitpid(pid, &status, 0);
+	return 1;
+}
+
+static void append_unsandboxed_output(char *result_buf, size_t max_len, size_t *total,
+                                      const char *chunk, size_t n)
+{
+	size_t add = n;
+	if (*total + add >= max_len - 1)
+		add = max_len - 1 - *total;
+	if (add == 0)
+		return;
+	memcpy(result_buf + *total, chunk, add);
+	*total += add;
+	result_buf[*total] = '\0';
+}
+
 /* ------------------------------------------------------------------ */
 /* Unsandboxed execution (fork + poll + waitpid)                        */
 /* ------------------------------------------------------------------ */
@@ -68,7 +114,6 @@ static int run_unsandboxed(const char *command, int timeout_sec,
 	size_t total = 0;
 	int timed_out = 0;
 	int elapsed_ms = 0;
-	int status;
 	char buf[256];
 	if (pipe(pipefd) != 0) {
 		snprintf(result_buf, max_len, "{\"error\":\"pipe failed\"}");
@@ -86,9 +131,11 @@ static int run_unsandboxed(const char *command, int timeout_sec,
 		dup2(pipefd[1], STDOUT_FILENO);
 		dup2(pipefd[1], STDERR_FILENO);
 		close(pipefd[1]);
+		(void)setpgid(0, 0);
 		execl("/bin/sh", "sh", "-c", command, (char *)NULL);
 		_exit(127);
 	}
+	(void)setpgid(pid, pid);
 	close(pipefd[1]);
 	result_buf[0] = '\0';
 	while (total < max_len - 1 && elapsed_ms < timeout_sec * 1000) {
@@ -102,28 +149,27 @@ static int run_unsandboxed(const char *command, int timeout_sec,
 		rem = timeout_sec * 1000 - elapsed_ms;
 		if (rem > 5000) rem = 5000;
 		r = poll(&pfd, 1, rem);
-		if (r < 0) break;
+		if (r < 0) {
+			if (errno == EINTR) continue;
+			break;
+		}
 		if (r == 0) {
 			elapsed_ms += rem;
 			if (elapsed_ms >= timeout_sec * 1000) {
 				timed_out = 1;
-				kill(pid, SIGKILL);
+				kill_command_tree(pid);
 				break;
 			}
 			continue;
 		}
-		n = read(pipefd[0], buf, sizeof(buf) - 1);
+		n = read(pipefd[0], buf, sizeof(buf));
 		if (n <= 0) break;
-		buf[n] = '\0';
-		{
-			size_t add = (size_t)n;
-			if (total + add >= max_len - 1) add = max_len - 1 - total;
-			memcpy(result_buf + total, buf, add + 1);
-			total += add;
-		}
+		append_unsandboxed_output(result_buf, max_len, &total, buf, (size_t)n);
 	}
+	result_buf[total] = '\0';
 	close(pipefd[0]);
-	waitpid(pid, &status, 0);
+	if (reap_running_child(pid))
+		timed_out = 1;
 	if (timed_out && total < max_len - 32)
 		snprintf(result_buf + total, max_len - total, "\n[Command timed out]");
 	return 0;
diff --git a/tests/test_shell.c b/tests/test_shell.c
index 8b43d94..ceb9551 100644
--- a/tests/test_shell.c
+++ b/tests/test_shell.c
@@ -2,12 +2,20 @@
  * @file test_shell.c
  * @brief Unit tests for shell tool: safe commands, blocklist, timeout.
  */
+#define _POSIX_C_SOURCE 200809L
 
 #include "tools/tool.h"
 #include "tools/shell.h"
 #include "core/config.h"
+#include <ctype.h>
+#include <dirent.h>
+#include <fcntl.h>
+#include <signal.h>
 #include <stdio.h>
+#include <stdlib.h>
 #include <string.h>
+#include <time.h>
+#include <unistd.h>
 
 static int tests_run = 0;
 static int tests_failed = 0;
@@ -68,6 +76,195 @@ static void test_shell_missing_command(void)
 	MU_ASSERT(r == -1, "missing command returns -1");
 }
 
+static void output_cap_hang_watchdog(int sig)
+{
+	(void)sig;
+	fprintf(stderr, "FAIL: unsandboxed shell hung after filling the output cap\n");
+	_exit(2);
+}
+
+static int buf_has_nul(const char *buf, size_t n)
+{
+	size_t i;
+	for (i = 0; i < n; i++) {
+		if (buf[i] == '\0')
+			return 1;
+	}
+	return 0;
+}
+
+static int argv0_is_sleep(const char *arg0)
+{
+	const char *base;
+	if (!arg0 || !arg0[0])
+		return 0;
+	base = strrchr(arg0, '/');
+	base = base ? base + 1 : arg0;
+	return strcmp(base, "sleep") == 0;
+}
+
+static int cmdline_is_sleep_marker(const char *buf, size_t n, const char *marker)
+{
+	size_t i = 0;
+	const char *arg1;
+	if (n == 0 || !marker)
+		return 0;
+	while (i < n && buf[i] != '\0')
+		i++;
+	if (i >= n || i + 1 >= n)
+		return 0;
+	if (!argv0_is_sleep(buf))
+		return 0;
+	arg1 = buf + i + 1;
+	return strcmp(arg1, marker) == 0;
+}
+
+static int count_sleep_argv_proc(const char *marker)
+{
+	DIR *dir;
+	struct dirent *ent;
+	int count = 0;
+	dir = opendir("/proc");
+	if (!dir)
+		return -1;
+	while ((ent = readdir(dir)) != NULL) {
+		char path[64];
+		char buf[256];
+		ssize_t n;
+		int fd;
+		if (!isdigit((unsigned char)ent->d_name[0]))
+			continue;
+		if (snprintf(path, sizeof(path), "/proc/%s/cmdline", ent->d_name)
+		    >= (int)sizeof(path))
+			continue;
+		fd = open(path, O_RDONLY);
+		if (fd < 0)
+			continue;
+		n = read(fd, buf, sizeof(buf) - 1);
+		close(fd);
+		if (n <= 0)
+			continue;
+		buf[n] = '\0';
+		if (cmdline_is_sleep_marker(buf, (size_t)n + 1, marker))
+			count++;
+	}
+	closedir(dir);
+	return count;
+}
+
+static int ps_line_is_sleep_marker(char *line, const char *marker)
+{
+	char *s = line;
+	char *nl;
+	char *base;
+	size_t marker_len;
+	nl = strchr(line, '\n');
+	if (nl)
+		*nl = '\0';
+	while (*s == ' ' || *s == '\t')
+		s++;
+	base = strrchr(s, '/');
+	base = base ? base + 1 : s;
+	marker_len = strlen(marker);
+	if (strncmp(base, "sleep ", 6) != 0)
+		return 0;
+	return strcmp(base + 6, marker) == 0 && marker_len > 0;
+}
+
+static int count_sleep_argv_ps(const char *marker)
+{
+	FILE *fp;
+	char line[256];
+	int count = 0;
+	fp = popen("ps -axo args=", "r");
+	if (!fp)
+		return -1;
+	while (fgets(line, sizeof(line), fp) != NULL) {
+		if (ps_line_is_sleep_marker(line, marker))
+			count++;
+	}
+	(void)pclose(fp);
+	return count;
+}
+
+/* Linux CI: /proc cmdline. Darwin (no /proc): ps args. argv0 must be sleep. */
+static int count_sleep_argv(const char *marker)
+{
+	int n = count_sleep_argv_proc(marker);
+	if (n >= 0)
+		return n;
+	return count_sleep_argv_ps(marker);
+}
+
+static int sleep_argv_did_not_grow(const char *marker, int before)
+{
+	struct timespec ts;
+	int i;
+	for (i = 0; i < 20; i++) {
+		int now = count_sleep_argv(marker);
+		if (now >= 0 && now <= before)
+			return 1;
+		ts.tv_sec = 0;
+		ts.tv_nsec = 50 * 1000 * 1000;
+		(void)nanosleep(&ts, NULL);
+	}
+	return 0;
+}
+
+static void test_shell_caps_output_without_hanging(void)
+{
+	const tool_t *t = tool_shell_get();
+	char buf[64];
+	int r;
+	int before;
+	tool_shell_set_config(NULL);
+	memset(buf, 'B', sizeof(buf));
+	before = count_sleep_argv("9999");
+	MU_ASSERT(before >= 0, "can count sleep 9999 processes");
+	signal(SIGALRM, output_cap_hang_watchdog);
+	alarm(5);
+	/* Fill the 64-byte cap, then sleep so the child stays alive without
+	 * writing (SIGPIPE will not reap it). Unsandboxed waitpid used to block
+	 * forever on this path (#69).
+	 */
+	r = t->execute("{\"command\":\"printf '%080d' 0; sleep 9999\"}", buf,
+	               sizeof(buf));
+	alarm(0);
+	signal(SIGALRM, SIG_DFL);
+	MU_ASSERT(r == 0, "capped shell command returns");
+	MU_ASSERT(buf[0] == '0', "capped output starts with truncated zeros");
+	MU_ASSERT(buf_has_nul(buf, sizeof(buf)), "capped output is NUL-terminated");
+	MU_ASSERT(sleep_argv_did_not_grow("9999", before),
+	          "sequential sleep 9999 did not leak");
+}
+
+static void test_shell_caps_output_kills_background_sleep(void)
+{
+	const tool_t *t = tool_shell_get();
+	char buf[64];
+	int r;
+	int before;
+	tool_shell_set_config(NULL);
+	memset(buf, 'B', sizeof(buf));
+	before = count_sleep_argv("9998");
+	MU_ASSERT(before >= 0, "can count sleep 9998 processes");
+	signal(SIGALRM, output_cap_hang_watchdog);
+	alarm(5);
+	/* Shell can exit after printf while the background sleep stays in the
+	 * process group. Skipping kill_command_tree when waitpid already reaped
+	 * the shell leaked that grandchild (#96).
+	 */
+	r = t->execute("{\"command\":\"trap '' HUP; sleep 9998 & printf '%080d' 0\"}",
+	               buf, sizeof(buf));
+	alarm(0);
+	signal(SIGALRM, SIG_DFL);
+	MU_ASSERT(r == 0, "background capped shell command returns");
+	MU_ASSERT(buf[0] == '0', "background capped output is truncated zeros");
+	MU_ASSERT(buf_has_nul(buf, sizeof(buf)), "background capped output is NUL-terminated");
+	MU_ASSERT(sleep_argv_did_not_grow("9998", before),
+	          "background sleep 9998 did not leak");
+}
+
 int main(void)
 {
 	MU_RUN(test_shell_blocked_rm_rf);
@@ -75,6 +272,8 @@ int main(void)
 	MU_RUN(test_shell_ls_succeeds);
 	MU_RUN(test_shell_invalid_json);
 	MU_RUN(test_shell_missing_command);
+	MU_RUN(test_shell_caps_output_without_hanging);
+	MU_RUN(test_shell_caps_output_kills_background_sleep);
 	printf("%d tests run, %d failed\n", tests_run, tests_failed);
 	return tests_failed ? 1 : 0;
 }