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Gathering Information about the Target, use whois database query tools to get the
Details such as Domain name, IPaddress, Administrative Details, autonomous
system number, DNS etc.
Fingerprint web server to gather information such as server name, server type,
operating systems, application running on the server etc use fingerprint scanning
tools such as , Netcraft, HTTPrecon , ID Serve .
Crawel Website to gather Specific information from web pages, such as email addresses
Perform Directory Traversal Attack to access Restricted Directories and execute the
command from outside of the Web server root directories.
Performing vulnerability scanning to identify the weakness in the network use the
vulnerability scanning tools such as HPwebinspect, Nessus. and determine if the system
can be exploited.
Perform we cache poisoning attack to force the web servers cache to flush its actual
cache content and send a specifically crafted request which will be stored in the cache.
Perform session hijacking to capture valid session cookies and IDs,use tools such
as Burb suite , Firesheep ,jhijack to automated session hijacking.
Performing MITM attack to access the sensitive information by intercepting the altering
the communications between the end users and web servers.
Use tools such as webalizer, AWStats to examine the web server logs .
Source: https://gbhackers.com/web-server-penetration-testing-checklist/