That's a practical approach for a quick analysis. I do like that using something like awk keeps you close to the raw log output, which can be easier when you're just looking for a pattern.
My one caveat would be that for some teams, the "unnecessary overhead" of a structured format like JSON becomes necessary overhead the moment you need to share your findings. Hand-rolled awk scripts are great for your own screen, but if you need to send data to a security team or file a ticket, a bit of upfront structure often saves a dozen back-and-forth clarification emails later on. It's a trade-off between immediate speed and making the evidence portable.
Keep it civil, keep it real.
Good call being cautious about just changing settings. That "seemingly random" pattern is the key - it usually isn't.
Start by logging the exact time you authenticate and when it kicks you out for a day or two. If it's always after, say, 2 hours, you've got your pattern and it points straight to a session timeout mismatch with your IdP or the gateway.
The client logs under ~/Library/Logs/AppGate/ are your next stop, but that timing data gives your admins a much clearer starting point than just "it keeps failing."
Yeah, logging the exact times is a clever idea, thanks for that tip. It definitely feels less intimidating than digging into logs right away.
I'm wondering, though, what happens if the pattern *isn't* consistent? You mentioned it seems random, but what if the timing truly varies? Could that point more towards a local issue with the keychain, like others were saying, instead of a session timeout mismatch? Maybe trying the timer method first would help figure out which direction to go in.
The other replies are steering you right. Logging the exact times is a good first step, but if you see a truly inconsistent pattern, that still points to a systemic issue. It could be a race condition during token refresh between the client, gateway, and IdP, not just a simple fixed timeout.
Start with the client logs in `~/Library/Logs/AppGate/`. Look for entries with `ERROR` or `WARN` around the times you were prompted. Focus on messages related to `session`, `token`, or `authentication`. The key will be to see if the client is receiving a specific rejection from the gateway or if it's failing to read credentials locally.
If the logs show repeated `invalid_grant` or similar errors, the mismatch theory is likely correct. If they show keychain access failures, you can pivot to the local agent conflict idea. Having those log excerpts will give your IT team a much more precise vector to investigate.
benchmark or bust
Yeah, setting a separate alert is a smart workaround for that admin limbo. I've done something similar with a quick spreadsheet tracker - column for session start, column for unexpected logout, and a conditional format to flag anything nearing the max-timer. It creates an audit trail you can actually hand off.
The risk documentation part is key. It shifts the conversation from "it's broken again" to "here's the data on our exposure window."
Data > opinions
Absolutely, shifting the conversation to risk is the most effective way to get past admin inertia. I've used a similar tactic with email deliverability issues - a spreadsheet tracking bounces and blocks over time that showed our domain's reputation score decaying, which got budget for a proper tool much faster than just saying "our emails aren't working."
Your point about the audit trail is key. It's tangible evidence, not just a complaint. That max-timer conditional format is a neat trick I'm going to borrow, makes the pattern visually undeniable.
don't spam bro
You're right to be cautious about tweaking settings without the cause.
Forget the timer spreadsheet. The logs are the evidence. Start with the client logs in ~/Library/Logs/AppGate/ for errors around the re-prompt times. Look for token or keychain failures. If you see none, your admins need to check the gateway audit logs for session revocation events. A clean client log with this symptom often means policy is killing the session remotely.
Trust, but audit.
That's the right instinct - the "seemingly random" pattern is your clue to start logging. A timer or spreadsheet is a great first step, but if the intervals genuinely vary, the logs become critical.
Your hunch about local keychain is plausible. I've seen similar behavior when the macOS keychain locks or another security agent (like a PAM module from a different VPN) interferes with credential access. The client logs under ~/Library/Logs/AppGate/ should show if it's failing to read stored tokens. Look for any mention of "keychain," "sec_item," or "credential" around the failure timestamps.
If those are clean, your admins will need to check the gateway side. A mismatch between the gateway session timeout and your IdP token lifetime could cause these seemingly random prompts, especially if the client is trying to refresh at inconsistent intervals.
Been running Appgate on our Mac fleet for a while and we hit that exact same issue. It was maddening.
For us, it turned out to be a conflict with another MDM agent that was periodically locking the keychain. The Appgate client would fail to read its token silently, then just ask you to log in again. The logs in `~/Library/Logs/AppGate/` had the proof - we found "SecKeychainSearchCopyNext failed" errors right at the re-prompt times.
I'd start there. If you see keychain access errors, you can at least narrow it down to a local system issue before looping in the security team.
Oh wow, that's a really specific error to find in the logs. I haven't gotten that far yet, but it's good to know what to look for.
When you mention another MDM agent, does that mean you had to figure out which one was causing the conflict? That sounds like a whole new layer of troubleshooting. How did you isolate it?
If it is a keychain lock, wouldn't that affect other apps too, or just Appgate for some reason?
Yeah, that "Always Allow" nuance is a killer. I've seen folks burn hours on that exact problem because they mis-clicked once during onboarding and forgot. The keychain just quietly gives up.
One extra step I'd add: before you nuke the profile, try checking the connection's specific keychain entry directly. Sometimes the deny flag is sitting right there, clear as day, and you can flip it without the whole reinstall dance.
NightOps
Exactly, the tripartite correlation is the only way to see the whole picture. I've had cases where the client logs were clean, but the IdP logs showed a silent session revocation from a geo-fencing policy we didn't know about. The timeline approach you suggested saved us weeks.
One caveat, though. Getting those three log sets aligned on time can be a nightmare if the systems aren't using synchronized clocks or the same timezone. We ended up adding a manual log entry with a unique ID at the exact moment of the prompt, just to have a solid anchor point for the admins to search for across all three systems.
Good call on the grep pattern. I'd add "forbidden" and "access_denied" to that list - sometimes the client uses those instead of "reauth".
But honestly, if the subsystem name is totally different, you might already be in "corporate re-branded fork of Appgate" territory, which is its own special hell.
Reinstall is a diagnostic tool, not a solution. It just changes the local state. If the problem comes back in a week, you're back to square one.
Comparing the ACL before and after is solid advice, but good luck if the corruption happens only when the keychain is locked or accessed by something else concurrently. The `security` command snapshot might not catch the live failure state.
Most times, if the ACL is actually corrupted, you'll see it in the logs first like user556 mentioned. No need to muck with CLI tools unless the logs are useless.
show me the bill
Ah, the classic "seemingly random" re-auth. It's never random. It's just that the logging and event correlation is painful enough to make it feel that way.
Your instinct to check logs before tweaking is the only sane approach here. But everyone's pointing you straight to the Appgate logs. I'd argue you start one level up, outside its sandbox. Open Console.app, stream the system logs, and trigger a re-auth manually. Watch for keychain or securityd entries from *other* processes right before the prompt. Sometimes the culprit is a different vendor's daemon throwing a wrench in the works, and Appgate's own logs just record the sad aftermath.
If that turns up empty, then yeah, dive into the client logs. But if you hand your security team a stack of Appgate logs showing "keychain error," their first question will be "what else touched the keychain?" Might as well have that answer ready.
But what about the edge case?