diff --git a/gateway/run.py b/gateway/run.py
index bed0cbff762c..c5b5516cd6f9 100644
--- a/gateway/run.py
+++ b/gateway/run.py
@@ -1589,6 +1589,18 @@ if _config_path.exists():
             _trust_recent_seconds = _gateway_cfg.get("trust_recent_files_seconds")
             if _trust_recent_seconds is not None:
                 os.environ["HERMES_MEDIA_TRUST_RECENT_SECONDS"] = str(_trust_recent_seconds)
+            # Bridge gateway.platform_connect_timeout → the internal env var the
+            # connect path + Discord adapter ready-wait both read (#19776).
+            # Unlike the agent.*/display.* bridges above (config-authoritative),
+            # this env var is the manual-override escape hatch, so it WINS if
+            # already set explicitly; otherwise config.yaml supplies the value.
+            if (
+                "platform_connect_timeout" in _gateway_cfg
+                and not os.environ.get("HERMES_GATEWAY_PLATFORM_CONNECT_TIMEOUT", "").strip()
+            ):
+                os.environ["HERMES_GATEWAY_PLATFORM_CONNECT_TIMEOUT"] = str(
+                    _gateway_cfg["platform_connect_timeout"]
+                )
     except Exception as _bridge_err:
         # Previously this was silent (`except Exception: pass`), which
         # hid partial bridge failures and let .env defaults shadow
diff --git a/hermes_cli/config.py b/hermes_cli/config.py
index 5c568fd24fd2..5b2ad0fd9270 100644
--- a/hermes_cli/config.py
+++ b/hermes_cli/config.py
@@ -2686,6 +2686,17 @@ DEFAULT_CONFIG = {
     # Gateway settings — control how messaging platforms (Telegram, Discord,
     # Slack, etc.) deliver agent-produced files as native attachments.
     "gateway": {
+        # Seconds the gateway waits for a single messaging platform to finish
+        # connecting during startup (and on reconnect). Discord in particular
+        # can blow past the old fixed 30s when an account has many slash
+        # commands to sync (#19776: 90-173 skills → ~28-31s sync). Raise this
+        # if your gateway hits "discord connect timed out" / "Timeout waiting
+        # for connection to Discord" restart loops. ``0`` or negative disables
+        # the timeout entirely (wait indefinitely). Bridged at startup to the
+        # internal HERMES_GATEWAY_PLATFORM_CONNECT_TIMEOUT env var, which still
+        # works as a manual override and wins if set explicitly.
+        "platform_connect_timeout": 30,
+
         # Scale-to-zero idle detection (Phase 0). The gateway watches for idle
         # and, when an instance is opted in via the NAS "Labs" toggle (carried as
         # the HERMES_SCALE_TO_ZERO env stamp) AND messaging is relay-only/absent
diff --git a/tests/gateway/test_config_env_bridge_authority.py b/tests/gateway/test_config_env_bridge_authority.py
index a82beb397b9d..f5e10408e4a5 100644
--- a/tests/gateway/test_config_env_bridge_authority.py
+++ b/tests/gateway/test_config_env_bridge_authority.py
@@ -46,6 +46,7 @@ def _run_gateway_import(hermes_home: Path, initial_env: dict[str, str]) -> dict[
             "HERMES_AGENT_TIMEOUT_WARNING",
             "HERMES_GATEWAY_BUSY_INPUT_MODE",
             "HERMES_GATEWAY_BUSY_TEXT_MODE",
+            "HERMES_GATEWAY_PLATFORM_CONNECT_TIMEOUT",
             "HERMES_TIMEZONE",
         ):
             v = os.environ.get(k)
@@ -81,13 +82,15 @@ def _run_gateway_import(hermes_home: Path, initial_env: dict[str, str]) -> dict[
 
 
 def _write_config(home: Path, agent_cfg: dict | None = None, display_cfg: dict | None = None,
-                  timezone: str | None = None) -> None:
+                  timezone: str | None = None, gateway_cfg: dict | None = None) -> None:
     import yaml
     cfg: dict = {}
     if agent_cfg:
         cfg["agent"] = agent_cfg
     if display_cfg:
         cfg["display"] = display_cfg
+    if gateway_cfg:
+        cfg["gateway"] = gateway_cfg
     if timezone:
         cfg["timezone"] = timezone
     (home / "config.yaml").write_text(yaml.safe_dump(cfg))
@@ -174,3 +177,29 @@ def test_env_value_survives_when_config_omits_key(hermes_home: Path) -> None:
     env = _run_gateway_import(hermes_home, initial_env={})
 
     assert env.get("HERMES_MAX_ITERATIONS") == "123"
+
+
+def test_config_platform_connect_timeout_supplies_env_when_unset(hermes_home: Path) -> None:
+    """config.yaml:gateway.platform_connect_timeout supplies the env var when
+    it isn't already set (#19776 — config surface for the Discord connect
+    timeout, replacing the undocumented env-var-only workaround)."""
+    _write_config(hermes_home, gateway_cfg={"platform_connect_timeout": 90})
+
+    env = _run_gateway_import(hermes_home, initial_env={})
+
+    assert env.get("HERMES_GATEWAY_PLATFORM_CONNECT_TIMEOUT") == "90"
+
+
+def test_env_platform_connect_timeout_wins_over_config(hermes_home: Path) -> None:
+    """Unlike the agent.*/display.*/timezone bridges (config-authoritative),
+    HERMES_GATEWAY_PLATFORM_CONNECT_TIMEOUT is the manual-override escape hatch:
+    an explicitly-set env var WINS over config.yaml. This divergence is
+    intentional (#19776) — the env var is the operator's emergency knob."""
+    _write_config(hermes_home, gateway_cfg={"platform_connect_timeout": 90})
+
+    env = _run_gateway_import(
+        hermes_home,
+        initial_env={"HERMES_GATEWAY_PLATFORM_CONNECT_TIMEOUT": "120"},
+    )
+
+    assert env.get("HERMES_GATEWAY_PLATFORM_CONNECT_TIMEOUT") == "120"
diff --git a/website/docs/reference/environment-variables.md b/website/docs/reference/environment-variables.md
index 1f42397ea229..35b34217cbab 100644
--- a/website/docs/reference/environment-variables.md
+++ b/website/docs/reference/environment-variables.md
@@ -686,7 +686,7 @@ Advanced per-platform knobs for throttling the outbound message batcher. Most us
 | `HERMES_VISION_DOWNLOAD_TIMEOUT` | Timeout in seconds for downloading an image before handing it to vision models (default: `30`). |
 | `HERMES_VISION_MAX_CONCURRENCY` | Max concurrent image **encode/resize** bursts across the whole process (override for `auxiliary.vision.max_concurrency`; default: host CPU core count, no ceiling). Bounds only the CPU-bound encode step so a video-frame fan-out can't saturate every core and starve the event loop — the LLM calls stay fully concurrent. Values `< 1` are ignored. |
 | `HERMES_RESTART_DRAIN_TIMEOUT` | Gateway: seconds to wait for active runs to drain on `/restart` before forcing the restart (default: `900`). |
-| `HERMES_GATEWAY_PLATFORM_CONNECT_TIMEOUT` | Per-platform connect timeout during gateway startup (seconds). |
+| `HERMES_GATEWAY_PLATFORM_CONNECT_TIMEOUT` | Per-platform connect timeout during gateway startup and reconnect (seconds; `0`/negative waits indefinitely). Applies to the connect attempt *and* the Discord adapter's ready-wait, so accounts with many slash commands to sync don't get killed mid-startup. Bridged from `gateway.platform_connect_timeout` in `config.yaml` (default `30`); this env var is the manual override and wins if set explicitly. |
 | `HERMES_GATEWAY_BUSY_INPUT_MODE` | Default gateway busy-input behavior: `queue`, `steer`, or `interrupt`. Can be overridden per chat with `/busy`. |
 | `HERMES_GATEWAY_BUSY_ACK_ENABLED` | Whether the gateway sends an acknowledgment message (⚡/⏳/⏩) when a user sends input while the agent is busy (default: `true`). Set to `false` to suppress these messages entirely — the input is still queued/steered/interrupts as normal, only the chat reply is silenced. Bridged from `display.busy_ack_enabled` in `config.yaml`. |
 | `HERMES_GATEWAY_NO_SUPERVISE` | Inside the s6-overlay Docker image, opt out of auto-supervision when running `hermes gateway run` and use pre-s6 foreground semantics (no auto-restart, gateway is the container's main process). Truthy values: `1`, `true`, `yes`. Equivalent to the `--no-supervise` CLI flag. No-op outside the s6 image. |