diff --git a/cron/scheduler.py b/cron/scheduler.py
index 876000a89..409ecb847 100644
--- a/cron/scheduler.py
+++ b/cron/scheduler.py
@@ -186,7 +186,14 @@ _SCRIPT_FAILURE_PHRASES = (
     "unable to execute",
     "permission denied",
     "no such file",
+    "no such file or directory",
+    "command not found",
+    "hermes binary not found",
+    "hermes not found",
     "traceback",
+    "ssh: connect to host",
+    "connection timed out",
+    "host key verification failed",
 )
 
 
diff --git a/cron/ssh_dispatch.py b/cron/ssh_dispatch.py
new file mode 100644
index 000000000..7aa6b79ba
--- /dev/null
+++ b/cron/ssh_dispatch.py
@@ -0,0 +1,275 @@
+"""SSH dispatch utilities for VPS agent operations.
+
+Provides validated SSH execution with proper failure detection.
+Used by cron jobs that dispatch work to remote VPS agents.
+
+Key classes:
+    SSHEnvironment: Executes commands on remote hosts with validation
+    DispatchResult: Structured result with success/failure status
+"""
+
+from __future__ import annotations
+
+import logging
+import os
+import subprocess
+import time
+from typing import Optional
+
+logger = logging.getLogger(__name__)
+
+_SSH_TIMEOUT = int(os.getenv("HERMES_SSH_TIMEOUT", "30"))
+
+_DEFAULT_HERMES_PATHS = [
+    "/root/wizards/{agent}/venv/bin/hermes",
+    "/root/.local/bin/hermes",
+    "/usr/local/bin/hermes",
+    "~/.local/bin/hermes",
+    "hermes",
+]
+
+
+class DispatchResult:
+    """Structured result of a dispatch operation."""
+
+    __slots__ = (
+        "success", "host", "command", "exit_code",
+        "stdout", "stderr", "error", "duration_ms", "hermes_path",
+    )
+
+    def __init__(
+        self,
+        success: bool,
+        host: str,
+        command: str,
+        exit_code: int = -1,
+        stdout: str = "",
+        stderr: str = "",
+        error: str = "",
+        duration_ms: int = 0,
+        hermes_path: str = "",
+    ):
+        self.success = success
+        self.host = host
+        self.command = command
+        self.exit_code = exit_code
+        self.stdout = stdout
+        self.stderr = stderr
+        self.error = error
+        self.duration_ms = duration_ms
+        self.hermes_path = hermes_path
+
+    def to_dict(self) -> dict:
+        return {
+            "success": self.success,
+            "host": self.host,
+            "exit_code": self.exit_code,
+            "error": self.error,
+            "duration_ms": self.duration_ms,
+            "hermes_path": self.hermes_path,
+            "stderr_tail": self.stderr[-200:] if self.stderr else "",
+        }
+
+    @property
+    def failure_reason(self) -> str:
+        if self.success:
+            return ""
+        if self.error:
+            return self.error
+        if "No such file" in self.stderr or "command not found" in self.stderr:
+            return f"Hermes binary not found on {self.host}"
+        if self.exit_code != 0:
+            return f"Remote command exited {self.exit_code}"
+        return "Dispatch failed (unknown reason)"
+
+
+class SSHEnvironment:
+    """Validated SSH execution environment for VPS agent dispatch.
+
+    Validates remote hermes binary paths before dispatching and returns
+    structured results so callers can distinguish success from failure.
+    """
+
+    def __init__(
+        self,
+        host: str,
+        agent: str = "",
+        ssh_key: str = "",
+        ssh_port: int = 22,
+        timeout: int = _SSH_TIMEOUT,
+        hermes_path: str = "",
+    ):
+        self.host = host
+        self.agent = agent
+        self.ssh_key = ssh_key
+        self.ssh_port = ssh_port
+        self.timeout = timeout
+        self.hermes_path = hermes_path
+        self._validated_path: str = ""
+
+    def _ssh_base_cmd(self) -> list[str]:
+        cmd = ["ssh", "-o", "StrictHostKeyChecking=accept-new"]
+        cmd.extend(["-o", "ConnectTimeout=10"])
+        cmd.extend(["-o", "BatchMode=yes"])
+        if self.ssh_key:
+            cmd.extend(["-i", self.ssh_key])
+        if self.ssh_port != 22:
+            cmd.extend(["-p", str(self.ssh_port)])
+        cmd.append(self.host)
+        return cmd
+
+    def _resolve_hermes_paths(self) -> list[str]:
+        if self.hermes_path:
+            return [self.hermes_path]
+        paths = []
+        for tmpl in _DEFAULT_HERMES_PATHS:
+            path = tmpl.format(agent=self.agent) if "{agent}" in tmpl else tmpl
+            paths.append(path)
+        return paths
+
+    def validate_remote_hermes_path(self) -> str:
+        """Probe the remote host for a working hermes binary.
+
+        Returns the validated path on success, raises RuntimeError on failure.
+        Caches the result so validation is only done once per instance.
+        """
+        if self._validated_path:
+            return self._validated_path
+
+        candidates = self._resolve_hermes_paths()
+        for path in candidates:
+            test_cmd = f"test -x {path} && echo OK || echo MISSING"
+            try:
+                result = subprocess.run(
+                    self._ssh_base_cmd() + [test_cmd],
+                    capture_output=True, text=True, timeout=self.timeout,
+                )
+                if result.returncode == 0 and "OK" in (result.stdout or ""):
+                    logger.info("SSH %s: hermes validated at %s", self.host, path)
+                    self._validated_path = path
+                    return path
+            except subprocess.TimeoutExpired:
+                logger.warning("SSH %s: timeout probing %s", self.host, path)
+                continue
+            except Exception as exc:
+                logger.debug("SSH %s: probe %s failed: %s", self.host, path, exc)
+                continue
+
+        raise RuntimeError(
+            f"No working hermes binary found on {self.host}. "
+            f"Checked: {', '.join(candidates)}."
+        )
+
+    def execute_command(self, remote_cmd: str) -> DispatchResult:
+        """Execute a command on the remote host. Returns DispatchResult."""
+        t0 = time.monotonic()
+        full_cmd = self._ssh_base_cmd() + [remote_cmd]
+        try:
+            result = subprocess.run(
+                full_cmd, capture_output=True, text=True, timeout=self.timeout,
+            )
+            elapsed = int((time.monotonic() - t0) * 1000)
+            stderr = (result.stderr or "").strip()
+            stdout = (result.stdout or "").strip()
+
+            if result.returncode != 0:
+                return DispatchResult(
+                    success=False, host=self.host, command=remote_cmd,
+                    exit_code=result.returncode, stdout=stdout, stderr=stderr,
+                    error=stderr.split("\n")[0] if stderr else f"exit code {result.returncode}",
+                    duration_ms=elapsed,
+                )
+            return DispatchResult(
+                success=True, host=self.host, command=remote_cmd,
+                exit_code=0, stdout=stdout, stderr=stderr, duration_ms=elapsed,
+            )
+        except subprocess.TimeoutExpired:
+            elapsed = int((time.monotonic() - t0) * 1000)
+            return DispatchResult(
+                success=False, host=self.host, command=remote_cmd,
+                error=f"SSH timed out after {self.timeout}s", duration_ms=elapsed,
+            )
+        except Exception as exc:
+            elapsed = int((time.monotonic() - t0) * 1000)
+            return DispatchResult(
+                success=False, host=self.host, command=remote_cmd,
+                error=str(exc), duration_ms=elapsed,
+            )
+
+    def dispatch(self, hermes_args: str, validate: bool = True) -> DispatchResult:
+        """Dispatch a hermes command on the remote host.
+
+        Args:
+            hermes_args: Arguments to pass to hermes (e.g. "cron tick").
+            validate: If True, validate the hermes binary exists first.
+
+        Returns DispatchResult. Only success=True if command actually ran.
+        """
+        if validate:
+            try:
+                hermes_path = self.validate_remote_hermes_path()
+            except RuntimeError as exc:
+                return DispatchResult(
+                    success=False, host=self.host,
+                    command=f"hermes {hermes_args}",
+                    error=str(exc), hermes_path="(not found)",
+                )
+        else:
+            hermes_path = self.hermes_path or "hermes"
+
+        remote_cmd = f"{hermes_path} {hermes_args}"
+        result = self.execute_command(remote_cmd)
+        result.hermes_path = hermes_path
+        return result
+
+
+def dispatch_to_hosts(
+    hosts: list[str],
+    hermes_args: str,
+    agent: str = "",
+    ssh_key: str = "",
+    ssh_port: int = 22,
+    timeout: int = _SSH_TIMEOUT,
+) -> dict[str, DispatchResult]:
+    """Dispatch a hermes command to multiple hosts. Returns host -> DispatchResult."""
+    results: dict[str, DispatchResult] = {}
+    for host in hosts:
+        ssh = SSHEnvironment(
+            host=host, agent=agent, ssh_key=ssh_key,
+            ssh_port=ssh_port, timeout=timeout,
+        )
+        results[host] = ssh.dispatch(hermes_args)
+        logger.info(
+            "Dispatch %s: %s", host,
+            "OK" if results[host].success else results[host].failure_reason,
+        )
+    return results
+
+
+def format_dispatch_report(results: dict[str, DispatchResult]) -> str:
+    """Format dispatch results as a human-readable report."""
+    lines = []
+    ok = [r for r in results.values() if r.success]
+    failed = [r for r in results.values() if not r.success]
+
+    lines.append(f"Dispatch report: {len(ok)} OK, {len(failed)} failed")
+    lines.append("")
+    for host, result in results.items():
+        status = "OK" if result.success else "FAILED"
+        line = f"  {host}: {status}"
+        if not result.success:
+            line += f" -- {result.failure_reason}"
+        if result.duration_ms:
+            line += f" ({result.duration_ms}ms)"
+        lines.append(line)
+
+    if failed:
+        lines.append("")
+        lines.append("Failed dispatches:")
+        for host, result in results.items():
+            if not result.success:
+                lines.append(f"  {host}: {result.failure_reason}")
+                if result.stderr:
+                    lines.append(f"    stderr: {result.stderr[-150:]}")
+
+    return "\n".join(lines)