Home > Articles > Microsoft > MCSE

VPNs: Dial "T" for Troubleshooting

Rebecca Rohan continues her discussion of how to create a virtual private network without having a virtual nervous breakdown. Just because the thing is built, that doesn't mean that you're done: Next comes a little phase called "troubleshooting."
Like this article? We recommend ***Production codes: - Title Page

In our last episode (part 1 of this series), IT superheroes learned to avert major disasters by planning the company VPN with uncanny forethought. Yet, even if you've done everything right (and that's a lot), you can still be confronted with problems. Users will louse things up with patches, new software, or just plain fiddling that overwrites your careful configurations on their end, from modem settings to WINS. There are firewalls that won't allow GRE packets and ISPs that block ports—and all that can change on someone else's whim. In short: Don't retire that red cape just yet.

Still, you don't have to fly around the world backward to fix VPN problems. We'll show you how simple many fixes can be, when you know how to look for the easy things first.

Your virtual private network is in place, and workers are attempting to tunnel in securely to perform their jobs. What's that you hear—a cry for help? In one of our favorite books on the topic, Implementing and Administering Security in a Windows 2000 Network Exam Cram 2 (Exam 70-214) (Que, 2003, ISBN 0789729512), authors Roberta Bragg and Ed Tittle say that when VPN connections aren't working, one simple test will probably rule out 50% of the rest of your entire VPN troubleshooting checklist: Simply find out whether other (presumably non–VPN) clients can connect to the server. Well done! It's much simpler to diagnose a VPN if you're not looking for something esoteric on both sides of a network connection—or analyzing the connection itself.

That's the kind of superhero you want to be—swoop in and point out a simple way to eliminate one huge vat of kryptonite, and then another. Point a finger at the server, and villains may fall out of its power supply vent and run cursing, "Drat! Foiled again!" when it can't perform normal tasks. Or it may be the client, which can't reach its ISP on a normal dial-up basis, let alone tunnel to work.

Match Game

Part 1 of this series talked about the buying decision between VPN products with IPsec or PPTP security protocols (or both), since protocols at the user's end and the company's end have to match. If the user is in trouble, does he have the security protocol that's configured at the server? Obviously, users need to match servers on network protocols (IPX or NetBEUI) and on the level of encryption, and you should have WINS enabled on both sides of the tunnel.

All these match points are places to recheck when things don't work correctly, but there are other spots to check for mismatches, including the authentication method for IPsec. AH and ESP encryption and authentication headers also have to match under IPsec. A roundabout "match": PPTP tunnels require MPPE encryption, so PPTP clients must be configured to use MS-CHP, MSCHAPv2, or EAP/TLS.

In Virtual Private Networks, Second Edition (O'Reilly, 1998), Mike Erwin, Charlie Scott, and Paul Wolfe remind IT superheroes of the simplest mismatch of all: "A mismatched username or password, which occurs when either the connecting machine or the far end thinks that the username or password is something other than what it is. This is sometimes caused by a simple typographical error." Lots of words for a short picture. This could also be the effect of a rollback on the user's machine due to a System Restore, so the login doesn't match information on the server. (See my article "Taking Advantage of Windows XP's System Restore," right here on Inform IT.) Just another non–VPN problem that can be isolated and fixed quickly by turning your x-ray vision on the ordinary problems first.

Any time technologies compound and become potential troubleshooting nightmares, the first principle of problem solving should always be going back to the source-and-buggy checklist that starts with questions like, "Is it plugged in?"

Pearson IT Certification Promotional Mailings & Special Offers

I would like to receive exclusive offers and hear about products from Pearson IT Certification and its family of brands. I can unsubscribe at any time.


Pearson Education, Inc., 221 River Street, Hoboken, New Jersey 07030, (Pearson) presents this site to provide information about Pearson IT Certification products and services that can be purchased through this site.

This privacy notice provides an overview of our commitment to privacy and describes how we collect, protect, use and share personal information collected through this site. Please note that other Pearson websites and online products and services have their own separate privacy policies.

Collection and Use of Information

To conduct business and deliver products and services, Pearson collects and uses personal information in several ways in connection with this site, including:

Questions and Inquiries

For inquiries and questions, we collect the inquiry or question, together with name, contact details (email address, phone number and mailing address) and any other additional information voluntarily submitted to us through a Contact Us form or an email. We use this information to address the inquiry and respond to the question.

Online Store

For orders and purchases placed through our online store on this site, we collect order details, name, institution name and address (if applicable), email address, phone number, shipping and billing addresses, credit/debit card information, shipping options and any instructions. We use this information to complete transactions, fulfill orders, communicate with individuals placing orders or visiting the online store, and for related purposes.


Pearson may offer opportunities to provide feedback or participate in surveys, including surveys evaluating Pearson products, services or sites. Participation is voluntary. Pearson collects information requested in the survey questions and uses the information to evaluate, support, maintain and improve products, services or sites; develop new products and services; conduct educational research; and for other purposes specified in the survey.

Contests and Drawings

Occasionally, we may sponsor a contest or drawing. Participation is optional. Pearson collects name, contact information and other information specified on the entry form for the contest or drawing to conduct the contest or drawing. Pearson may collect additional personal information from the winners of a contest or drawing in order to award the prize and for tax reporting purposes, as required by law.


If you have elected to receive email newsletters or promotional mailings and special offers but want to unsubscribe, simply email information@informit.com.

Service Announcements

On rare occasions it is necessary to send out a strictly service related announcement. For instance, if our service is temporarily suspended for maintenance we might send users an email. Generally, users may not opt-out of these communications, though they can deactivate their account information. However, these communications are not promotional in nature.

Customer Service

We communicate with users on a regular basis to provide requested services and in regard to issues relating to their account we reply via email or phone in accordance with the users' wishes when a user submits their information through our Contact Us form.

Other Collection and Use of Information

Application and System Logs

Pearson automatically collects log data to help ensure the delivery, availability and security of this site. Log data may include technical information about how a user or visitor connected to this site, such as browser type, type of computer/device, operating system, internet service provider and IP address. We use this information for support purposes and to monitor the health of the site, identify problems, improve service, detect unauthorized access and fraudulent activity, prevent and respond to security incidents and appropriately scale computing resources.

Web Analytics

Pearson may use third party web trend analytical services, including Google Analytics, to collect visitor information, such as IP addresses, browser types, referring pages, pages visited and time spent on a particular site. While these analytical services collect and report information on an anonymous basis, they may use cookies to gather web trend information. The information gathered may enable Pearson (but not the third party web trend services) to link information with application and system log data. Pearson uses this information for system administration and to identify problems, improve service, detect unauthorized access and fraudulent activity, prevent and respond to security incidents, appropriately scale computing resources and otherwise support and deliver this site and its services.

Cookies and Related Technologies

This site uses cookies and similar technologies to personalize content, measure traffic patterns, control security, track use and access of information on this site, and provide interest-based messages and advertising. Users can manage and block the use of cookies through their browser. Disabling or blocking certain cookies may limit the functionality of this site.

Do Not Track

This site currently does not respond to Do Not Track signals.


Pearson uses appropriate physical, administrative and technical security measures to protect personal information from unauthorized access, use and disclosure.


This site is not directed to children under the age of 13.


Pearson may send or direct marketing communications to users, provided that

  • Pearson will not use personal information collected or processed as a K-12 school service provider for the purpose of directed or targeted advertising.
  • Such marketing is consistent with applicable law and Pearson's legal obligations.
  • Pearson will not knowingly direct or send marketing communications to an individual who has expressed a preference not to receive marketing.
  • Where required by applicable law, express or implied consent to marketing exists and has not been withdrawn.

Pearson may provide personal information to a third party service provider on a restricted basis to provide marketing solely on behalf of Pearson or an affiliate or customer for whom Pearson is a service provider. Marketing preferences may be changed at any time.

Correcting/Updating Personal Information

If a user's personally identifiable information changes (such as your postal address or email address), we provide a way to correct or update that user's personal data provided to us. This can be done on the Account page. If a user no longer desires our service and desires to delete his or her account, please contact us at customer-service@informit.com and we will process the deletion of a user's account.


Users can always make an informed choice as to whether they should proceed with certain services offered by Adobe Press. If you choose to remove yourself from our mailing list(s) simply visit the following page and uncheck any communication you no longer want to receive: www.pearsonitcertification.com/u.aspx.

Sale of Personal Information

Pearson does not rent or sell personal information in exchange for any payment of money.

While Pearson does not sell personal information, as defined in Nevada law, Nevada residents may email a request for no sale of their personal information to NevadaDesignatedRequest@pearson.com.

Supplemental Privacy Statement for California Residents

California residents should read our Supplemental privacy statement for California residents in conjunction with this Privacy Notice. The Supplemental privacy statement for California residents explains Pearson's commitment to comply with California law and applies to personal information of California residents collected in connection with this site and the Services.

Sharing and Disclosure

Pearson may disclose personal information, as follows:

  • As required by law.
  • With the consent of the individual (or their parent, if the individual is a minor)
  • In response to a subpoena, court order or legal process, to the extent permitted or required by law
  • To protect the security and safety of individuals, data, assets and systems, consistent with applicable law
  • In connection the sale, joint venture or other transfer of some or all of its company or assets, subject to the provisions of this Privacy Notice
  • To investigate or address actual or suspected fraud or other illegal activities
  • To exercise its legal rights, including enforcement of the Terms of Use for this site or another contract
  • To affiliated Pearson companies and other companies and organizations who perform work for Pearson and are obligated to protect the privacy of personal information consistent with this Privacy Notice
  • To a school, organization, company or government agency, where Pearson collects or processes the personal information in a school setting or on behalf of such organization, company or government agency.


This web site contains links to other sites. Please be aware that we are not responsible for the privacy practices of such other sites. We encourage our users to be aware when they leave our site and to read the privacy statements of each and every web site that collects Personal Information. This privacy statement applies solely to information collected by this web site.

Requests and Contact

Please contact us about this Privacy Notice or if you have any requests or questions relating to the privacy of your personal information.

Changes to this Privacy Notice

We may revise this Privacy Notice through an updated posting. We will identify the effective date of the revision in the posting. Often, updates are made to provide greater clarity or to comply with changes in regulatory requirements. If the updates involve material changes to the collection, protection, use or disclosure of Personal Information, Pearson will provide notice of the change through a conspicuous notice on this site or other appropriate way. Continued use of the site after the effective date of a posted revision evidences acceptance. Please contact us if you have questions or concerns about the Privacy Notice or any objection to any revisions.

Last Update: November 17, 2020