Palo Alto’s Chief Information Officer is Unable or Unwilling to Get to the Core of a Problem

When our email kept getting bounced back, I set out to find out why by asking the head of the Information Technology Department for the city of Palo Alto, Jonathan Reichental, Ph.D., and recent hire.

His background is impressive with a long list of accomplishments in the private sector: PricewaterhouseCoopers, Avida consulting and O’Reilly Media.

“Jonathan was the clear frontrunner in our recruitment,” Keene said in the release announcing his hire. “He brings a combination of creative and entrepreneurial drive and skills and a commitment to taking city government to the forefront of public technology and innovation, befitting Palo Alto, the heartbeat of Silicon Valley.”

He is also described as “a passionate technologist” among other charming, descriptive terms as mentioned in his Press Release, which includes the paltry compensation package of 180k a year. So, one would think that as a passionate technologist he would have a clear understanding of technology issues centering around email systems.

On many different levels one can equate this email disconnect with a government agency as a public utility problem.  And the problem thus far appears to be with the city of Palo Alto’s email server.  Through a series of emails sent to the chief technology officer, Mr. Reichental, I  thought he would get at the core of the issues as to why our emails were bouncing back from (No pun intended)

What our readers need to be aware of is that city attorney Donald Larkin was quietly blacklisting many email addresses criticizing local government leadership activities and preventing them from reaching their intended persons. A constitutional violation without the benefit of due process of law.

Mr. Larkin’s legal interpretation of harassment when sending multiple emails to the same persons and or the use of blind copies was later reversed by newly appointed city attorney Molly Stump.  In a brief interview Ms. Stump stated, ‘she doesn’t want any emails blocked coming into city offices’.  So we were surprised when we received the following message back from the city’s email server.

Delivery has failed to these recipients or groups:
This message was rejected by the recipient e-mail system. Please check the recipient’s e-mail address and try resending this message, or contact the recipient directly.

Diagnostic information for administrators: Generating server:
#554 5.1.0 Sender denied ##

Original message headers:

Final-Recipient: rfc822; Action: failed Status: 5.1.0 Diagnostic-Code: smtp;554 5.1.0 Sender denied

Here’s the technical response we received back to my underling concerns of Mr. Larkin quietly blocking and or filtering emails classified as government critical spam.

Hi Mark:

We’ve reviewed your request below and found the following: We found no obvious server-side restriction on this email. There are any number of other reasons it could have bounced outside of my teams control. This person retired last year and the email address has been disabled. A bounced email is the correct outcome.



Jonathan Reichental, Ph.D. :: Chief Information Officer :: City of Palo Alto :: @Reichental
Assistant: :: 650-329-2182

Problem persists:

Hi Jonathan:

Still rejected. Have any idea?


Ps. Would you run an additional test on your side so we can get to the bottom of this?  Perhaps have this employee send me an email.  I’m surprised this was not done. Lastly do employees have the capability to set there own spam filters. Was this question asked and or pursued.

The final technical response received from the city’s top Chief Information Officer: 

Hi Mark:

We’ve confirmed that her email is functioning correctly. We don’t know why you are getting bounced. Sorry I can’t assist further.

All the best.


Jonathan Reichental, Ph.D. :: Chief Information Officer :: City of Palo Alto :: @Reichental
Assistant: :: 650-329-2182

This story is far from being over.

We plan to take a bite out of the kara apple figuratively ourselves and see what we come up with.

There are several things we find troubling.  First, We’ve lost our email connection with our local government news media representative. Secondly, Mr. Reichental appears to be uninterested as a public government servant in solving this problem.

Lets not forget. He works for us and at a salary of 180 thousand dollars.  So, we should be able at the very least, get something in return for our hard pressed taxpayer dollars.  Weather or not the blocking of our email address is intentional or unintentional.  We intend to find out why.

One Reply to “Palo Alto’s Chief Information Officer is Unable or Unwilling to Get to the Core of a Problem”

  1. There are many things that needs to be checked
    1) Transport Rules on Exchange
    2) Forefront (or any spam filtering software implemented)
    3) check communication with the email using simple test on
    4) Check users’ junk mail
    5) etc
    Don’t give up! 🙂 Never give up! 🙂

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