diff --git a/content/manuals/ai/governance/local/network-rules.md b/content/manuals/ai/governance/local/network-rules.md
index 632f135ce34a..05179f5806f0 100644
--- a/content/manuals/ai/governance/local/network-rules.md
+++ b/content/manuals/ai/governance/local/network-rules.md
@@ -79,6 +79,10 @@ Write the host without a scheme, such as `api.github.com` rather than
 include a port, but it must be a hostname. To match an IP address or a CIDR
 range, use a network rule without `--method` or `--path`.
 
+Paths and query parameter names and values ignore ASCII letter case. For
+examples and wildcard behavior, see
+[HTTP rules](../reference/network-rules.md#http-method-and-path).
+
 ### Choose methods
 
 Pass several methods as a comma-separated list, or `ANY` to match every
diff --git a/content/manuals/ai/governance/organization/policies/filesystem.md b/content/manuals/ai/governance/organization/policies/filesystem.md
index b24ac2037782..be98c6d8a4d8 100644
--- a/content/manuals/ai/governance/organization/policies/filesystem.md
+++ b/content/manuals/ai/governance/organization/policies/filesystem.md
@@ -36,7 +36,10 @@ Each filesystem mount rule allows or denies `read`, `write`, or both on the
 host paths it lists. A read-only workspace needs only `read`, and a writable
 workspace needs both. Paths can use wildcards, and `~` expands to each user's
 home directory, so a single `~/**` rule matches every developer's home tree.
-For the path formats on each operating system and how wildcards match, see
+
+POSIX path matching is case-sensitive, including on macOS. Windows drive paths
+and UNC paths, including WSL UNC paths, match without regard to case. For path
+formats and matching details, see
 [Filesystem mount rule syntax](../../reference/filesystem-rules.md).
 
 ## When changes take effect
diff --git a/content/manuals/ai/governance/reference/filesystem-rules.md b/content/manuals/ai/governance/reference/filesystem-rules.md
index e2291f67698f..094c8fb73c66 100644
--- a/content/manuals/ai/governance/reference/filesystem-rules.md
+++ b/content/manuals/ai/governance/reference/filesystem-rules.md
@@ -36,6 +36,14 @@ location that several platforms share needs a rule for each:
 On Windows, `*:` matches any drive letter, so `*:\data\**` matches the path on
 any drive.
 
+Case sensitivity depends on the path format:
+
+- POSIX paths on macOS and Linux are case-sensitive: `/data/Project/**` doesn't
+  match `/data/project/file`. Use the directory names' capitalization on disk,
+  even on a case-insensitive macOS volume.
+- Windows drive paths and UNC paths, including WSL UNC paths, are
+  case-insensitive: `C:\Data\Project\**` matches `c:\data\project\file`.
+
 Wildcards behave the same way in every path format:
 
 | Pattern            | Example    | Matches                                                    |
diff --git a/content/manuals/ai/governance/reference/network-rules.md b/content/manuals/ai/governance/reference/network-rules.md
index 5d26fbfde857..fa4c97f48ca2 100644
--- a/content/manuals/ai/governance/reference/network-rules.md
+++ b/content/manuals/ai/governance/reference/network-rules.md
@@ -42,7 +42,11 @@ for an organization policy and
 [Allow or block HTTP methods and paths](../local/network-rules.md#allow-or-block-http-methods-and-paths)
 for a local one.
 
-Path patterns follow the same wildcard rules as filesystem paths, where `*`
+HTTP path matching ignores ASCII letter case: `/API/**` matches `/api/items`.
+Non-ASCII characters remain case-sensitive. This applies to both allow and deny
+rules.
+
+Path patterns use the same wildcards as filesystem paths, where `*`
 matches within one path segment and `**` matches any depth. A pattern without a
 wildcard matches that path exactly, so `/repos` matches `/repos` and nothing
 below it. Every pattern must start with `/` and can't contain a query string, a
@@ -56,7 +60,8 @@ An HTTP rule can also restrict query parameters independently of the path.
 
 Use exact parameter names and values, or a single `*` at the start or end of a
 value to match a suffix or prefix. A value of `*` matches any value, including
-an empty one. Names cannot contain wildcards. Names and values are
+an empty one. Names cannot contain wildcards. Names and values ignore ASCII
+letter case, so `Tag=PROD` matches `tag=prod`. Non-ASCII characters remain
 case-sensitive.
 
 For rules created with `--query`, every specified parameter must match.
@@ -103,6 +108,8 @@ ICMP is blocked.
 
 ### Hostname patterns
 
+Hostname matching is case-insensitive: `EXAMPLE.com` matches `example.com`.
+
 | Pattern               | Example           | Matches                                                      |
 | --------------------- | ----------------- | ------------------------------------------------------------- |
 | Exact hostname        | `example.com`     | `example.com` on any port, not subdomains                     |
diff --git a/content/manuals/ai/governance/troubleshooting.md b/content/manuals/ai/governance/troubleshooting.md
index 8cc6ec16a173..21c8f0ecd5b3 100644
--- a/content/manuals/ai/governance/troubleshooting.md
+++ b/content/manuals/ai/governance/troubleshooting.md
@@ -115,7 +115,8 @@ details, see
 If a sandbox fails to mount with a `mount policy denied` error, an organization
 filesystem policy doesn't allow the path. Check that the filesystem allow rule
 uses `**` rather than `*`. A single `*` doesn't match across directory
-separators. For more details, see
+separators. For macOS and Linux paths, also check that the rule matches the
+directory names' capitalization on disk. For more details, see
 [Organization filesystem access policies](organization/policies/filesystem.md).
 
 ## Organization policy changes aren't taking effect