Inky Week in Review!

INKY Week in Review Study Guide

INKY Week in Review

INKY Week in Review Study Guide

Built from INKY Support Chat — the questions techs asked, the answers given, and the tips and updates shared by Engineering and Product. Organized by topic so a recurring question gets answered once, here, instead of re-asked in chat every week.

Assumed coverage window: week of Aug 31 – Sept 4, 2026 for week 1; Sept 4–22, 2026 for week 2 (a wider window since that source material was compiled as a single period). Let James know if either range should be dated differently.

2 updates logged 8 topic areas 24 Q&A entries 8 knowledge-check questions

Highlighted content with a NEW badge was added from the Sept 4–22, 2026 update.

Weekly Log

#Week ofFocus areasNotes
1 Aug 31 – Sept 4, 2026 Mail flow ownership, Outlook/link/list questions, security detection gaps, KaseyaOne & domain provisioning, Autotask/Bullhorn integrations First edition — baseline content.
2 Sept 4 – 22, 2026 Authentication/cache issues, domain & tenant migration, Microsoft 365 Groups migration, Threat Center permissions, production-access roles, mail flow/pre-INKY failures, encrypted attachments, sign-in event retention, compliance documentation, license upgrades, API lifecycle, offboarding/uninstall, Google Workspace protection scope Sourced from the Channel Q&A Training Guide (Sept 4–22, 2026). One item (Google Workspace protection scope) is unresolved — flagged for escalation rather than answered with a guess.

A row gets added here after each future update, then the details are folded into the topic sections below — same pattern as the SMTP field guide.

Before You Post — Start Here

Post non-Dev questions in Internal – Inky Inquires first, before pinging engineering directly. Use this format:

Ticket #  |  Reason for swarm  |  Symptoms  |  Specific question

Giving all four up front is what makes a swarm fast — it's the single biggest lever for getting a quick, accurate answer instead of a back-and-forth.

New — Sept 22, 2026

Escalation evidence checklist (applies to any escalation, not just this update's items)

  • Ticket number and business impact
  • INKY team ID, organization ID, region, and affected user or domain
  • Exact error text and timestamp with timezone
  • Message trace, message ID, .eml or headers when mail flow is involved
  • What Support reproduced and what changed between working and failing tests
  • Production access approval when backend or tenant changes may be required
  • A focused question for L2 or Engineering, not only a symptom summary

Topics

Confirming INKY actually processed a message: look for message trace hops and headers such as X-Rerouted-To-Inky and X-IPW-Processed. If those indicators are present, INKY was in the path.

If a rule fired but INKY indicators are absent: the problem is upstream of INKY. Check inbound connectors, disabled rules, custom rule order, and third-party routing before assuming INKY is involved at all.

Attributing a failure after INKY finished: if INKY completed processing cleanly and Exchange then fails during mailbox delivery, treat Microsoft as the likely owner of the issue, not INKY. Week 1's examples included ticket EX1464935 and poison-message errors.

Q: Exchange poison-message errors — what's going on?

Answer The reviewed failure occurred in Microsoft's mailbox delivery, after handoff from INKY — INKY had already completed its part.

First action Use message trace to pinpoint exactly which stage failed, and check Microsoft service health when the failure happens after Microsoft accepted the message.

New — Sept 22, 2026

Q: How can Support determine whether a reported delivery failure is actually caused by INKY?

Confirmed answer Check Microsoft message trace and identify where the failure occurs. If mail fails before it is sent to INKY, the issue is not caused by INKY and would occur even without INKY in the path.

Coaching note Use precise trace evidence before escalating to INKY Engineering.

Source: Sept 21

Tips — mail flow and authentication
  • Don't change INKY-created connectors without evidence that the connector configuration itself is wrong.
  • Different "From" values can be normal: the metadata Mail From is the envelope sender, while the visible From is the header sender. A mismatch can also indicate spoofing — don't assume either way without checking.
  • If a third-party system sends as the customer's own users or domains, working authentication for that traffic matters. If it instead sends from its own domain, Known External Sender may be the more appropriate classification.

Bulk Safe Senders: no supported CSV or bulk-import workflow currently exists — this came up with a request for roughly 1,000 Safe Senders at once. Manual paste may work as a workaround; otherwise, submit a feature request for a real bulk-import path.

Allow-list and link-rewrite changes are not retroactive: they don't cause previously delivered mail to be reprocessed. A confirmed Safe report can still affect click-time protection going forward, but it won't reach back and change what already landed.

Classic Outlook flagging grammar in the banner: traced to Microsoft Editor (Classic Outlook's newer grammar engine) evaluating the banner and quoted text as if it were the user's own writing, rather than skipping it.

Q: Outlook flags banner grammar — how do we fix it?

Answer Classic Outlook's newer Microsoft Editor can evaluate banner and quoted text for grammar, which it shouldn't.

First action Apply a no-proofing style manually or via VBA. New Outlook was reported to behave correctly, so switching clients is also a valid workaround.

Q: An existing/already-delivered link is still blocked — why won't it clear?

Answer Allow-list and Link Rewrite Exception changes are not retroactive, and they do not automatically extend to subdomains.

First action Add the exact host to the exception list, and separately confirm a Safe report on the already-delivered link, since the exception alone won't touch mail already in the inbox.

Q: How do we bulk-load Safe Senders?

Answer No supported CSV or bulk-import workflow was identified.

First action Paste properly formatted entries manually if the volume is workable; submit a feature request for true bulk import if not.

Tips — reports, policies, and exceptions
  • Have recipients report questionable messages through the banner — reviewing the reported variations is how detection actually improves over time.
  • Allow lists can suppress detections outright. If a suspicious message comes back with a weaker verdict than expected, review existing allow rules before looking anywhere else.
  • Link Rewrite Exceptions only affect in-flight mail — they can't "un-rewrite" a link that was already delivered, and subdomains may need their own explicit entries.
  • Learning Mode does not remove the banner. What it actually does is suppress the First Time Sender warning specifically — worth clarifying with customers who expect it to turn banners off entirely.

Compromised internal senders: treat as an account-takeover scenario. Reset the account, strengthen MFA, enable ATO (Account Takeover) detection where appropriate, and make sure affected messages get reported through the banner so the sample feeds back into detection.

Known gap — "Potential Fake Conversation": this detection did not trigger on a fabricated invoice thread in week 1. It remains an open Engineering/Product review item and a possible real detection gap, not just a one-off miss.

Q: Internal phishing is reaching the Inbox — what do we do?

Answer Treat internal malicious mail as a possible account compromise, not just a detection miss.

First action Disable the account, reset credentials, require strong MFA, review ATO Detection settings, and report the messages so they're captured for analysis.

Q: A new phishing-simulation provider isn't being recognized — how do we get it added?

Answer Engineering needs actual reported samples and raw details from the messages to evaluate what makes that provider's simulations identifiable.

First action Report the sample messages as Safe, provide the supporting evidence, and escalate to development for evaluation.

New — Sept 22, 2026

Q: Can INKY detect malicious content inside a password-protected or encrypted attachment?

Confirmed answer If INKY cannot access the password, it generally cannot fully analyze the encrypted contents. In some cases, if the password can be identified from the message, it may be used for analysis. Otherwise, INKY may only warn that the attachment could not be fully analyzed.

Coaching note Set expectations carefully: encrypted content limits inspection depth.

Source: Sept 17

Tips — phishing simulations and integrations
  • For a new simulation provider, report several sample messages and include raw data so engineering can determine the provider's identifying signals — one sample usually isn't enough to build a reliable pattern.
  • A recognized phishing simulation should not be blocked by Link Protection. If it is, capture the exact Observation URL and verify settings at the time of analysis — don't assume it's expected behavior.
  • Whether a provider can get a reusable, standing exception depends on whether its identification is consistent across customers; tenant-specific IPs or on-prem appliances may need custom, per-tenant setup instead.

KaseyaOne identity-provider login errors: resolved in several cases in week 1 simply by clearing cached authentication data and retesting — worth trying before escalating.

Partner IDs are permanent: they're fixed internal identifiers and cannot be renamed once provisioned. (Consistent with how INKY org IDs work more broadly — see the SMTP field guide's Kaseya One topic.)

.onmicrosoft.com license failures: can trace back to missing MX records, incomplete Exchange Online setup, or simply a new tenant that's still propagating. Don't assume the license itself is broken before checking those three.

Releasing inactive-team domains: can be done after validation, so the domain can then be onboarded to the correct team cleanly.

Q: Tenant address discovery is failing — where do we look?

Answer The reviewed .onmicrosoft.com domain had no MX result and may not have had Exchange Online fully configured yet.

First action Verify MX records, Exchange service setup, and DNS propagation before retrying licensing.

Q: KaseyaOne authentication error — what's the fix?

Answer Similar identity-provider errors were resolved in week 1 after backend cache clearing.

First action Clear cache, retry sign-in, and confirm the result before escalating further.

Tips — tenant, team, and onboarding notes
  • Team IDs cannot be reused or edited once provisioned; the team name, by contrast, remains customizable at any time.
  • When moving a domain off an inactive team: confirm the domain has actually been removed in Microsoft first, then release it from the old INKY team before onboarding it elsewhere — order matters here.
  • For a fully defunct team, the preferred approach is the partner's built-in self-service reset/offboarding flow, with backend cleanup only when needed on top of that.
  • A newly verified domain may still be missing Exchange service setup, or may simply still be propagating — don't treat either as a failure yet.

Autotask mappings that save and then revert: should be escalated for development review. Confirmed in week 1: the integration itself does not determine the destination queue, so a reverting mapping points to a bug, not a config mistake.

Bullhorn false positives: require checking authentication, source/origin, auto-forwarding behavior, and the INKY result together — no single field tells the whole story.

INKY Setup & Maintenance app permissions: needs elevated access during initial setup. If a customer's security team raises audit questions about this, point them to the documented enterprise-app purpose and the approved post-setup permission guidance rather than improvising an answer.

Q: Bullhorn mail is going to Junk — why?

Answer Check origin and authentication together. The specific case reviewed in week 1 showed an auto-forward with no authentication, while an allow list was separately suppressing internal-name scoring — two contributing factors, not one.

First action Require valid authentication when mail is sent as customer domains; consider Known External Sender when Bullhorn is sending from its own domain instead.

Q: How much access does the Setup & Maintenance app actually need?

Answer Global Admin is needed during setup. That can be reduced afterward.

First action Reduce the app's access to Exchange Administrator once setup is complete, where appropriate for the tenant.

Fast triage questions — work through these before escalating
  • Did the message actually traverse INKY?
  • Are connectors and transport rules enabled and ordered correctly?
  • Did Microsoft fail after INKY returned the message?
  • Is the behavior future-only, rather than retroactive?
  • Is this documentation, configuration, a backend action, product behavior, or a potential bug?

What to capture for fast triage, every time: the exact tenant/team, message ID or Observation URL, trace, authentication results, screenshots, and the raw sample. Having these ready up front is what turns a slow back-and-forth into a same-day answer.

Escalation package — what L2/engineering will ask for: ticket summary, tenant/team, exact symptom, expected vs. actual behavior, timestamps, message ID, Observation URL, trace, screenshots, raw message, and the steps already completed. See also the Escalation Evidence Checklist under "Before You Post" above.

Tips — investigation essentials
  • For detection or analysis issues, get a reported message or the specific Observation URL before doing anything else — it makes the investigation materially faster than working from a description alone.
  • Ask for the exact INKY team, time period, and message ID before concluding whether encryption, routing, or analysis was actually involved.
  • Use Microsoft message trace to determine where a failure happened: before INKY, during INKY processing, or after Microsoft accepted the message. This single check resolves most "whose fault is it" questions.
Tips — partner handling and escalation
  • Document troubleshooting and evidence in the ticket before requesting an L2 or engineering swarm — see the Start Here format above.
  • A partner request alone does not guarantee an immediate L2 call. Set expectations with the partner and route follow-up through the original ticket.
  • When Microsoft trace shows INKY completed processing and Microsoft failed at delivery, avoid presenting the issue to the customer as an INKY outage without further evidence — that framing is usually wrong and hard to walk back.
New — Sept 22, 2026

All of Topic 7 is new this update, sourced from the Sept 4–22 Channel Q&A Training Guide.

Q: A user receives "Unexpected error when authenticating with identity provider" when signing in to INKY. What should Support do?

Confirmed answer A backend cache clear may be required. After the cache is cleared, have the user retry authentication. If the error persists, capture the user email, team or organization, login path, timestamp, and whether other KaseyaOne modules work.

Coaching note Do not present browser-cache clearing as the confirmed fix when the pattern points to an INKY-side login cache.

Source: Sept 22

Q: Does an ATO Enforcement Approver also need a Policy Admin or Super Admin role?

Confirmed answer Yes. The approver currently needs Policy Admin or higher to view or act on enforcements.

Coaching note If an org-level role does not grant expected team access, the behavior may be unintended. Group-based role updates can take up to 10 minutes for cache refresh.

Source: Sept 21

Q: A partner owner is a Policy Admin but needs to perform all MSP actions. Should Support uninstall for them or change the role?

Confirmed answer The preferred option was to change the partner owner from Policy Admin to Super Admin so the partner can perform the work directly. Production access approval is required for Support to make the role change.

Coaching note Support should avoid performing partner actions when the partner can be enabled to complete them safely.

Source: Sept 16

New — Sept 22, 2026

All of Topic 8 is new this update, sourced from the Sept 4–22 Channel Q&A Training Guide.

Q: A domain was moved to a different Microsoft 365 tenant but is still attached to the original INKY team. Can it be released without offboarding the original team?

Confirmed answer Yes. First verify that the domain is now associated with a different Microsoft tenant, then remove only that domain from the original INKY team. Keep the remaining active team unchanged.

Coaching note A public tenant-ID lookup was cited as a way to compare the Microsoft tenant IDs before removal.

Source: Sept 8 and Sept 14

Q: Microsoft 365 Groups migration returns "Migrate groups failed." What does this usually indicate?

Confirmed answer The observed failure looked like a timeout while INKY was updating rules with newly created group names before Microsoft had fully surfaced the groups. Review the migration logs. The recommended recovery was to uninstall and reinstall so the latest rules are created for the new groups.

Coaching note Use the available logs before classifying the issue. The generic UI error alone is not enough.

Source: Sept 16

Q: How long are Microsoft 365 sign-in events retained in the INKY Sign-In Events dashboard?

Confirmed answer The answer provided in the channel was 30 days.

Coaching note Confirm against current product documentation if a partner needs a contractual or compliance statement.

Source: Sept 14

Q: Who can provide INKY SOC 2 or ISO documentation when normal channels are not responding?

Confirmed answer The INKY Product Manager stated that they could share the SOC 2 report directly and moved the exchange to a one-to-one conversation.

Coaching note Do not attach controlled compliance reports to open channels. Route through the approved owner.

Source: Sept 11

Q: How is an INKY Advanced-to-Pro upgrade handled?

Confirmed answer The Account Manager is involved in obtaining the license. For an MSP, Support may need to modify the INKY selection after permission is granted. For a client tenant, the MSP can generally make the change.

Coaching note A control can appear visually grayed out while still being selectable. Verify by clicking and confirm the Salesforce or subscription entitlement before treating it as a UI defect.

Source: Sept 17

Q: Can Support provide an API key for a Cork integration?

Confirmed answer An existing API approach was described as being deprecated. Cork will need to move to the new API after general availability, while the beta was described as limited launch.

Coaching note Avoid promising general-availability dates beyond the explicitly communicated roadmap.

Source: Sept 17

Q: A partner removed the Microsoft 365 integration before uninstalling INKY. What is the recovery path?

Confirmed answer Regrant API access from the INKY dashboard, then run the normal uninstall before removing the Microsoft applications. If access cannot be restored, the partner must manually remove INKY rules and connectors; Support can then coordinate the license reset after the cleanup is confirmed.

Coaching note Sequence matters: uninstall first, remove Microsoft applications afterward.

Source: Sept 21–22

Q: Why can an uninstall fail after a customer domain moves to another Microsoft 365 tenant?

Confirmed answer The original onmicrosoft.com or certificate domain may remain tied to the first tenant while the custom domain has moved to a different tenant. INKY may still need access to the original tenant to remove the installed artifacts.

Coaching note Capture both Microsoft tenant IDs and determine where the certificate domain and original installation remain.

Source: Sept 22

Q: Can a Google Workspace tenant protect and bill for only one user by temporarily adding several users and later removing them?

Confirmed answer Unresolved. The channel contained the question but no confirmed answer in the available result set. Treat this as unresolved and escalate for product confirmation before advising on billing or protection behavior.

Coaching note Never convert an unconfirmed workaround into standard practice.

Source: Sept 22

Knowledge Check

Quick self-test — try answering before revealing each one.

1. Which headers prove INKY processing?

2. Do exceptions (allow-list, link-rewrite) apply retroactively?

3. What points to Microsoft ownership of a failure, rather than INKY's?

4. When is clearing cached auth data the appropriate fix?

5. What belongs in the Internal – Inky Inquires triage post?

6. New What role does an ATO Enforcement Approver need, at minimum, to act on enforcements?

7. New Can a password-protected attachment be fully analyzed by INKY?

8. New When a Microsoft 365 Groups migration fails, what's the recommended recovery?

Internal reference — INKY Support Chat weekly study guide. Built from chat activity; update after each week rather than starting a new document, same as the SMTP field guide.

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