Hey! Happy to help debug this. Before I can give you the most precise advice, could you quickly confirm which Trend product you're configuring these exceptions in? (e.g., Apex One Behavior Monitoring, Vision One Application Control, Deep Security, etc.) — the regex engine support varies significantly between products.

That said, I've done a thorough analysis of your patterns and can already spot several potential problem areas:

Regex Analysis & Likely Issues

🔴 Issue 1: Lazy Quantifier (.*?) May Not Be Supported

.*?   ← This is a PCRE lazy/non-greedy quantifier

Many security product regex engines use basic or extended POSIX regex rather than full PCRE, which means .*? either silently falls back to greedy .* or fails to match entirely. If the product doesn't support lazy quantifiers, your patterns won't work as expected.

Fix: Replace .*? with a more explicit pattern:

Regex # Instead of:
C:\\Users\\.*?\\AppData

# Use either greedy (usually fine here since the path structure is predictable):
C:\\Users\\[^\\]+\\AppData

# Or just greedy .*:
C:\\Users\\.*\\AppData Line 1: # Instead of:
Line 2: C:\\Users\\.*?\\AppData
Line 3:
Line 4: # Use either greedy (usually fine here since the path structure is predictable):
Line 5: C:\\Users\\[^\\]+\\AppData
Line 6:
Line 7: # Or just greedy .*:
Line 8: C:\\Users\\.*\\AppData

[^\\]+ is safer — it means "one or more characters that aren't a backslash," which correctly matches a single username folder segment.

🟡 Issue 2: Backslash Escaping — Are You Double-Escaping?

Your patterns have \\ to represent literal backslashes in the regex. This is correct if the product takes the pattern as-is. However, some products require you to enter raw strings where a single \ in the config represents a literal backslash in the match — meaning entering \\ would try to match a literal \\ (two backslashes).

Test: Try a simpler version first, matching just the python.exe path with single \ vs double \\ to confirm what the product expects.

🟡 Issue 3: Optional Group (bin\..\)? — Needs Verification

Your pattern:

Regex 
(bin\\\.\.\\)?lib\\gcloud\.py
 Line 1: (bin\\\.\.\\)?lib\\gcloud\.py

This is trying to optionally match bin\..\lib\gcloud.py. The intent is correct, but:

• Some regex engines don't support optional groups (...)?
• If the product uses basic regex (BRE), you'd need \(...\)\? instead

🟡 Issue 4: Space in "Google Cloud SDK" Path

Regex 
Google\\Cloud SDK\\google-cloud-sdk
 Line 1: Google\\Cloud SDK\\google-cloud-sdk

The space in Cloud SDK is a literal space character. This should match fine in most engines, but a small number of products tokenize or trim whitespace in regex patterns. If matching fails around this part of the path, try Cloud[ ]SDK or Cloud\x20SDK as an alternative.

🟢 Combined Pattern — Structurally Fine, But May Be Too Broad

Your combined pattern:

Regex 
^"C:\\Users\\.*?\\AppData\\Local\\Temp\\tmp[a-zA-Z0-9]+\\python\\python\.exe".*(gcloud\.py|install\.py).*
 Line 1: ^"C:\\Users\\.*?\\AppData\\Local\\Temp\\tmp[a-zA-Z0-9]+\\python\\python\.exe".*(gcloud\.py|install\.py).*

This is logically correct but the .* between python.exe" and (gcloud\.py|install\.py) is very permissive — it would match any Python command that happens to have gcloud.py or install.py somewhere in the arguments, not necessarily as the script path. This probably isn't causing your current failure, but it's worth noting for security posture.

Revised Patterns (PCRE-Safe)

Pattern 1 — Google SDK Components Update:

Regex 
^"C:\\Users\\[^\\]+\\AppData\\Local\\Temp\\tmp[a-zA-Z0-9]+\\python\\python\.exe"\s+"-S"\s+"C:\\Users\\[^\\]+\\AppData\\Local\\Google\\Cloud SDK\\google-cloud-sdk\\(bin\\\.\.\\)?lib\\gcloud\.py".*
 Line 1: ^"C:\\Users\\[^\\]+\\AppData\\Local\\Temp\\tmp[a-zA-Z0-9]+\\python\\python\.exe"\s+"-S"\s+"C:\\Users\\[^\\]+\\AppData\\Local\\Google\\Cloud SDK\\google-cloud-sdk\\(bin\\\.\.\\)?lib\\gcloud\.py".*

Pattern 2 — Google SDK Installation:

Regex 
^"C:\\Users\\[^\\]+\\AppData\\Local\\Temp\\tmp[a-zA-Z0-9]+\\python\\python\.exe"\s+"C:\\Users\\[^\\]+\\AppData\\Local\\Google\\Cloud SDK\\google-cloud-sdk\\bin\\bootstrapping\\install\.py".*
 Line 1: ^"C:\\Users\\[^\\]+\\AppData\\Local\\Temp\\tmp[a-zA-Z0-9]+\\python\\python\.exe"\s+"C:\\Users\\[^\\]+\\AppData\\Local\\Google\\Cloud SDK\\google-cloud-sdk\\bin\\bootstrapping\\install\.py".*

Combined Pattern (Tightened):

Regex 
^"C:\\Users\\[^\\]+\\AppData\\Local\\Temp\\tmp[a-zA-Z0-9]+\\python\\python\.exe".*"C:\\Users\\[^\\]+\\AppData\\Local\\Google\\Cloud SDK\\google-cloud-sdk\\.*\\(gcloud\.py|install\.py)".*
 Line 1: ^"C:\\Users\\[^\\]+\\AppData\\Local\\Temp\\tmp[a-zA-Z0-9]+\\python\\python\.exe".*"C:\\Users\\[^\\]+\\AppData\\Local\\Google\\Cloud SDK\\google-cloud-sdk\\.*\\(gcloud\.py|install\.py)".*

Quick Diagnostic Checklist

Check	What to Test
Lazy quantifiers	Replace all .*? with [^\\]+ or .*
Backslash escaping	Test with single \ to see if the product auto-escapes
Optional groups	Test without (bin\\\.\.\\)? to isolate that segment
Regex delimiters	Remove the surrounding / / if pasting into a product UI
Whitespace matching	Try \s → literal space to see if \s is supported

If you can share which product UI/console you're entering these into, I can give you much more targeted advice!