The Capital of Silicon Valley struggles with email system
San Jose City Hall is pictured in this file photo.

    Despite complaints and frustration from the mayor about San Jose’s email platform, the city can’t afford to switch its operating system.

    “That kind of migration and transition would be a huge project for (roughly) 7,000 city employees,” Chief Information Officer Rob Lloyd told San José Spotlight.

    San José Spotlight last week revealed that Mayor Sam Liccardo relies heavily on his private Gmail account to conduct city business. More than 1,600 pages of records released to San José Spotlight and its attorney Karl Olson show Liccardo sends and receives hundreds of city-related messages every month through his private account.

    The mayor has faced scrutiny—and a Supreme Court case in 2017—over his use of a private email account. Using private email to conduct city business could potentially lead to California Public Records Act violations, free speech experts and media lawyers say. Liccardo has also failed to turn over private emails that should be public record, as reported exclusively by San José Spotlight.

    Liccardo claims he relies on his private account, even though it raises transparency concerns, because the city’s Microsoft Outlook system doesn’t work for him. He cites problems with emails not sending, syncing and slow service.

    “We were finding that emails were being caught in an outbox rather than actually getting sent, and I wouldn’t know about that until weeks later,” Liccardo told San José Spotlight last week. “So it’s just easier to use Gmail.”

    The mayor declined further comment this week.

    A known problem

    Liccardo said the issues with Microsoft Outlook—which also include crashing, not updating calendar invites and delays in accessing Zoom—make it difficult for him and his staff to get work done.

    The problems with syncing and crashing have always existed, Lloyd said, but became more apparent in the last two years, especially during the COVID-19 pandemic as traffic on the city website intensified.

    “We have a very digital public and a very digital workforce now,” Lloyd said. “These tools came from a generation when that wasn’t necessarily the case.”

    Working with outdated technology has frustrated other city officials as well. San Jose Councilmember Dev Davis uses a separate database to keep track of inquiries and concerns from residents.

    “These concerns with (Outlook) have been well-documented,” Davis told San José Spotlight. “They are basic functions that don’t work.”

    During a City Council meeting in April, Davis listed a number of concerns with the email provider as councilmembers discussed Microsoft’s contract renewal. Yet the mayor and his colleagues voted unanimously to renew the contract for five years and pay the tech company $9.7 million. Liccardo and Davis asked the city to work with Microsoft to resolve the problems and report on solutions by year’s end.

    Microsoft declined to comment through a spokesperson.

    Seeking solutions

    Lloyd said San Jose is working with Microsoft on these issues. The challenge is identifying root causes and testing solutions before rolling out changes. It’s not a quick fix.

    The teams that handle emails from the public, such as those sent to city councilmembers, are impacted by Outlook’s glitches, Lloyd said, though that isn’t a large part of City Hall’s workforce.

    Microsoft’s menu of services continue to be a popular government platform due to exclusive integration of programs with departments such as human resources and payroll. Google Workspace doesn’t offer such services.

    Lloyd pointed out that a hybrid solution might work in the future. He said Los Angeles kept a good number of Microsoft licenses when the city switched to Google’s platform in 2009.

    For now, San Jose has scrapped a previously discussed pilot program with Google Workspace.

    The five-year contract with Google would have cost San Jose about $2.4 million less upfront. But it would have been a wash after paying for transition costs and necessary Microsoft programs, Lloyd said at the April council meeting.

    “If you take a look across all of governments, Microsoft is still the predominant player by far,” Lloyd told San José Spotlight. “But I think as time goes on you’ll continue to see folks transition.”

    Contact Tran Nguyen at [email protected] or follow @nguyenntrann on Twitter. 

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