Hi @Pratik Vaidya ,
Please check your IIS Compression module, make sure that dynamic content and static content all enabled.
If you enable failed request tracing to check compression, you will find that static compression won't work when a static file didnot get hit frequently.
If you rely this request doezens times, the header will appear.
Another thing, there's a limit for minimum file size for compression. You can modify that value according to your application.
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Best regards,
Bruce Zhang