Web server pentesting performing under 3 major category which is identity, Analyse, Report Vulnerabilities such as authentication weakness, configuration errors, protocol Relation vulnerabilities.

1. “Conduct a serial of methodical and Repeatable tests “ is the best way to test the web server along with this to work through all of the different application Vulnerabilities.

2. “Collecting as Much as Information” about an organization Ranging from operation environment is the main area to concentrate on the initial stage of web server Pen testing.

3. Performing web server Authentication Testing, use Social engineering techniques to collect the information about the Human Resources, Contact Details, and other Social Related information.

4. Gathering Information about Target, use whois database query tools to get the Details such as Domain name, IP address, Administrative Details, autonomous system number, DNS etc.

5. Fingerprint webserver to gather information such as server name, server type, operating systems, an application running on the server etc use fingerprint scanning tools such as, Netcraft, HTTPrecon, ID Serve.

6. Crawel Website to gather Specific information from web pages, such as email addresses

7. Enumerate web server Directories to extract important information about web functionalities, login forms etc.

8. Perform Directory traversal Attack to access Restricted Directories and execute the command from outside of the Web server root directories.

9. 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.

10. Perform we cache poisoning attack to force the web server’s cache to flush its actual cache content and send a specifically crafted request which will be stored in the cache.

11. Performing HTTP response splitting attack to pass malicious data to a vulnerable application that includes the data in an HTTP response header.

12. Bruteforce SSH ,FTP , and other services login credentials to gain unauthorized access.13. Perform session hijacking to capture valid session cookies and ID’s ,use tools such as Burb suite , Firesheep , jhijack to automated session hijacking.

14. Performing a MITM attack to access sensitive information by intercepting the communications between the end-users and web servers.

15. Use tools such as Webalizer, AWStats to examine the web server logs .

Important Checklist Suggested by Microsoft

Services

Unnecessary Windows services are disabled.

Services are running with least-privileged accounts.

FTP, SMTP, and NNTP services are disabled if they are not required.

Telnet service is disabled.

Protocols

WebDAV is disabled if not used by the application OR it is secured if it is required.

TCP/IP stack is hardened

NetBIOS and SMB are disabled (closes ports 137, 138, 139, and 445).

Accounts

Unused accounts are removed from the server.

Guest account is disabled.

IUSR_MACHINE account is disabled if it is not used by the application.

If your applications require anonymous access, a custom least-privileged anonymous account is created.

The anonymous account does not have write access to Web content directories and cannot execute command-line tools.

Strong account and password policies are enforced for the server.

Remote logons are restricted. (The “Access this computer from the network” user-right is removed from the Everyone group.)

Accounts are not shared among administrators.

Null sessions (anonymous logons) are disabled.

Approval is required for account delegation.

Users and administrators do not share accounts.

No more than two accounts exist in the Administrators group.

Administrators are required to log on locally OR the remote administration solution is secure.

Files and Directories

Files and directories are contained on NTFS volumes

Web site content is located on a non-system NTFS volume.

Log files are located on a non-system NTFS volume and not on the same volume where the Web site content resides.

The Everyone group is restricted (no access to \WINNT\system32 or Web directories).

Web site root directory has denied write ACE for anonymous Internet accounts.

Content directories have deny write ACE for anonymous Internet accounts.

Remote administration application is removed

Resource kit tools, utilities, and SDKs are removed.

Sample applications are removed

Shares

All unnecessary shares are removed (including default administration shares).

Access to required shares is restricted (the Everyone group does not have access).

Administrative shares (C$ and Admin$) are removed if they are not required (Microsoft Management Server (SMS) and Microsoft Operations Manager (MOM) require these shares).

Ports

Internet-facing interfaces are restricted to port 80 (and 443 if SSL is used)

Intranet traffic is encrypted (for example, with SSL) or restricted if you do not have a secure data center infrastructure.

Registry

Remote registry access is restricted.

SAM is secured (HKLM\System\CurrentControlSet\Control\LSA\NoLMHash).

Auditing and Logging

Failed logon attempts are audited.

IIS log files are relocated and secured.

Log files are configured with an appropriate size depending on the application security requirement.

Log files are regularly archived and analyzed.

Access to the Metabase.bin file is audited.

IIS is configured for W3C Extended log file format auditing.

Server Certificates

Ensure certificate date ranges are valid.

Only use certificates for their intended purpose (For example, the server certificate is not used for e-mail).

Ensure the certificate’s public key is valid, all the way to a trusted root authority.

Confirm that the certificate has not been revoked.

Also Read Penetration testing Android Application checklist

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