Mayor Antonio Villaraigosa favors the effort to modernize the e-mail system. His spokesman, Matt Szabo, described the current software, which is neither from Microsoft nor Google, as a slow, "inefficient, crash-prone e-mail system."
Los Angeles city officials last year solicited bids for a new system. Both Microsoft and Google submitted proposals; Google Apps got the nod because city administrators believed it would be cheaper and less labor-intensive.
The contract has passed one council committee and must still pass a second before it goes to a final vote by the full City Council.
No date has been set for that vote, but lobbyists and representatives from both companies have descended on City Hall in teams of 10 at times, council members said, armed with digital presentations and documents to make their cases.
According to records from the city's Ethics Commission, Microsoft has spent more than $40,000 this year on all Los Angeles city-related lobbying, including by Fernando Guerra, a veteran consultant who is active at City Hall. Google and Computer Sciences Corp. -- the company that hopes to install the Google system -- registered lobbyists this year as well, paying them less than $10,000 in the same time period.
Microsoft has also sought to undermine the claim that Google offers the potential for big savings, pointing to what it calls optimistic estimates by city officials. The city's projected savings are based in part on expected gains in worker productivity, a quantity that is difficult to nail down.
Those concerns were repeated by Parks, who at a recent technology committee meeting grilled Randi Levin, the city's chief technology officer and a Google proponent.
"Are you saying where these savings are coming from?" Parks asked. "Are they real dollars -- dollars we can depend on down the road?"
The matter is expected to go to the budget committee, headed by Parks, on Oct. 5. Parks' office said he was still reviewing the proposal and had not yet stated his position.
Critics of the Google proposal have also raised the touchy issue of data security. If the city's e-mail and documents are stored on Google's remote servers, the city would be relying on the company to protect potentially sensitive information, including from the Police Department and city attorney's office.
A memo circulated to city officials by Microsoft representatives argued that "Google is not terribly transparent about security issues," before adding that "Microsoft believes Google can be secure, but do they have the experience to get that way fast. We know how hard those growing pains can be."
In response, Google asserted that its cloud-based system can quickly deploy upgrades and security updates to all of its customers, something that is less seamless when organizations maintain their own computer systems on site.
"In the last 12 months alone, Microsoft has released 70 security patches, 41 of which were classified as 'critical' security issues," Google spokesman Andrew Kovacs said in an e-mail. Because those security updates are often not installed right away, Kovacs wrote, "the bad guys have a road map to the flaw."
Google recently announced it would launch a "government cloud" next year, designed to meet the more strenuous security and regulatory requirements of government entities.
To date, some of Google's highest-profile converts have been college campuses. Officials at UC Davis, Notre Dame and Arizona State University all reported that students were happy with the system -- and that administrators were happy with the cost.
"I think it's one of the most amazing things we've done for students in the last five years," said Kari Barlow, an assistant vice president in Arizona State's technology office.
With those victories under its belt, Google appears bent on gaining even more ground. In a rare move, the advertising-shy company launched a billboard campaign in San Francisco, New York, Boston and Chicago last month encouraging businesses to switch to Google Apps.
"Just heard about going Google," the boards said on the first day of the campaign. "I want to know more."
Times staff writer David Zahniser contributed to this report.