Purview auto-apply retention label policies enabled in Enforce mode but never stamping labels on validated content (E5 Developer tenant)

Question

Summary

I have multiple Microsoft Purview auto-apply retention label policies that are Enabled in Enforce mode but are not stamping labels on qualifying SharePoint content. A separate policy has been stuck in simulation at "0 of 1 locations scanned" for over 5 days. All customer-side configuration has been validated end-to-end. Looking for guidance on what service-side conditions could cause this or how to diagnose further.

Environment

• Tenant SKU: Microsoft 365 E5 Developer Trial (without Windows and Audio Conferencing)
• Test user licensing: E5 Developer assigned; "Information Protection for Office 365 – Premium" service plan enabled
• Test site: Single SharePoint communication site (POV_test)
• Auto-label scope: Static, one explicit site included

Policies in play

| Policy | Type | Status | Condition |

|---|---|---|---|

| Auto-label Policy - Retain 10 Years (2ndtry) | Auto-apply | Enabled (Enforce) | RefinableString00:"10 year" |

| Auto-label Policy - Test Document | Auto-apply | Enabled (Enforce) | keyword "Test Document" |

| RetentionAuto-labelingPolicy | Auto-apply | Stuck In simulation, 0 of 1 locations scanned, 5+ days | — |

| Auto-label Policy - RT (diagnostic) | Auto-apply | Enabled (Enforce) | RefinableString00:test |

| PublishTest | Publish | Enabled (Static) | — |

Retention label: Retain 10 Years — retain 10 years → delete → based on when last modified.

What I've validated / ruled out

• ✅ Custom document property written to Office file, promoted to SharePoint library column
• ✅ Crawled property ows_Retention present in Search Schema; mapped to managed property RefinableString00
• ✅ SharePoint Search query RefinableString00:"10 year" returns the correct file today (confirmed after multiple reindex cycles)
• ✅ Retention label configuration verified
• ✅ Publish policy Enabled, Static, explicit site scope
• ✅ Auto-label policy scope type = Static (verified via Edit wizard)
• ✅ Auto-label policy locations = SharePoint classic and communication sites only, 1 explicit site
• ✅ Auto-label policy label and Mode = Enforce (verified on Review/Finish page)
• ✅ Licensing (E5 with IP for Office 365 – Premium enabled)
• ✅ Orphaned "Auto Apply - Retain 10 Years" retention policy showing "Settings not found" has been deleted
• ✅ Test documents modified after both policies were enabled
• ✅ SharePoint tokenizer treats 10 year and 10year identically (rules out any space/word-break hypothesis)
• ✅ Fresh diagnostic policy created against a fresh file with a single-token metadata value (Retention=test) validated in SharePoint Search — same result (no label stamped)
• ✅ Admin account added to Records Management, Compliance Administrator, Compliance Data Administrator role groups

Current symptom

For the target file (Test Doc - Class4 -10year.docx):

• Compliance Details: Label Status: None, "This item is not subject to a retention policy"
• Retention Label column: blank
• No stamping observed 5+ days after policy enablement

Question

Given all customer-side prerequisites appear validated — KQL condition works in SharePoint Search, licensing is correct, publish + auto-label policies are Enabled in Enforce mode, site scope is explicit — what service-side conditions or diagnostics would explain an auto-apply policy being Enabled but never processing content in a specific SharePoint site?

Answer 1

Hi @CH-SolutionsEngineer,
Based on the information you've shared, you've already validated most of the common customer-side prerequisites, including search indexing, managed property mapping, policy scope, licensing, publish policy, and auto-apply policy configuration.

If the KQL query is returning the expected document, the policies are enabled in Enforce mode, and the site is explicitly included, the remaining possibilities are generally service-side, such as:

• The auto-labeling processing pipeline hasn't yet picked up the policy or queued the SharePoint site for evaluation.
• The policy evaluation job is delayed or stalled, which could also explain why the simulation policy has remained at 0 of 1 locations scanned for more than five days.
• The compliance processing service hasn't synchronized the latest search index or policy changes for the targeted site.
• A tenant-specific issue affecting the auto-labeling workload, particularly if the behavior is isolated to this tenant.

Before concluding that this is a service-side issue, I'd recommend a few additional checks:

1. Wait at least 7 days after enabling the auto-apply policy, as policy processing isn't immediate and can take several days, especially in test environments.
2. Create a brand-new test document after the policy is already in Enforce mode, place it in the same site, and verify whether it gets labeled. This helps rule out documents that weren't picked up during an earlier processing cycle.
3. Test a simpler auto-apply condition, such as a keyword that appears in the document content instead of a managed property, to determine whether the issue is specific to managed property evaluation or whether no auto-labeling jobs are processing at all.
4. Review the Microsoft Purview audit log, if available, for any retention label events. If there are no auto-labeling or retention label actions recorded for the test document, it would suggest the policy evaluation isn't reaching the document.

One additional question: have you observed the same auto-labeling configuration working in any other production or non-developer tenant, or is this only occurring in your Microsoft 365 E5 Developer tenant?

The answer will help determine whether this is a tenant-specific processing issue or something related to the environment itself.