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Dear Miss Manners • In the past few weeks, I have noticed several cashiers and bank tellers asking if I have any plans for the day, or asking

On April 19, three weeks before he called the end of the 30-year bull market in bonds, Bill Gross said he was buying inflation-linked Treasuries, a bet that money printing by the world’s central banks would push up consumer prices.

While Treasuries subsequently fell as he had predicted, so did inflation expectations, amplifying rather than limiting losses for Gross’s Pimco Total Return Fund, which had 12 percent of its $289 billion in Treasury Inflation-Protected Securities, or TIPS, at the end of the first quarter. The world’s largest mutual fund fell 4.7 percent in May and June, prompting $9.9 billion in withdrawals last month, the most on record.

The losses highlight the difficulties Gross faces as he steers Pacific Investment Management Co. through what’s arguably the biggest market challenge for the $2 trillion bond-fund manager since its inception in 1971. A premature bet against Treasuries caused his flagship to trail peers in 2011, prompting Gross to apologize to clients. With about 10 percent of the TIPS market owned by Pimco, according to Morningstar Inc. Gross’ success is tied in part to an asset class fellow bond manager Jeffrey Gundlach has avoided.

“Unless inflation goes higher, then all you have with TIPS is interest rate risk, just like every other Treasury,” said Gundlach, the portfolio manager for the $39 billion DoubleLine Total Return Bond Fund. “It’s an asset class that is exposed to investor surprise and disappointment.”

Gundlach, who called TIPS a “disaster” and a “trap” during a webcast last month, lost 2.6 percent in the two months through June and is down 0.3 percent so far this year in his main fund, beating 83 percent of peers. None of Gundlach’s funds reported holding any TIPS as of March 31.

Gross didn’t return an email seeking comment.

Gross has had between 9 percent to 12 percent of Pimco Total Return’s net assets invested in TIPS since at least the end of 2011, convinced that efforts by U.S. Federal Reserve Chairman Ben Bernanke and other central bankers to stimulate their economies will ultimately fuel inflation. The government bonds provide protection against inflation by increasing in par value with the U.S. Consumer Price Index.

At the end of the first quarter, Pimco Total Return had about 33 percent of its net assets invested in Treasuries, including $52.9 billion of traditional or “nominal” bonds and $34.3 billion of TIPS. The latter proved costly during the second quarter, when TIPS swooned under muted inflation expectations and sales by certain risk-parity funds, which typically have a high portion of their assets invested in TIPS and other inflation-linked bonds.

The TIPS held by PIMCO as of March 31 declined in value by $3.9 billion during the second quarter, according to data through June 28 compiled by Bloomberg. In contrast, the value of the fund’s holdings in nominal Treasuries fell by about $1.9 billion, assuming the holdings were unchanged.

Gross made another bad bet on Treasuries almost 2½ years ago. In February 2011, he eliminated his allocation to Treasuries, only to miss out on a rally in government bonds that left Pimco Total Return trailing 70 percent of peers. Gross, in a letter to clients at the time titled “Mea Culpa,” called 2011 a “stinker.” His fund lost an estimated $5 billion to withdrawals that year, according to Morningstar.

Pimco Total Return rebounded in 2012 to beat 95 percent of peers and has outperformed 93 percent of rivals over the past five years, according to data compiled by Bloomberg.

SURPRISE RISE IN TIPS YIELD

The fund’s allocation to Treasuries, a category that also includes futures, rose to 39 percent in April and then dipped to 37 percent in May, when Bernanke told Congress that the central bank’s policy-setting board could begin to curtail quantitative easing in “its next few meetings” if the Fed is confident gains in the economy can be sustained. Bernanke expanded on his comments last month, telling reporters that the central bank will probably taper its $85 billion bond buying program later this year, as long as the economy performs in line with Fed projections.

While the yield on 10-year Treasuries soared as high as 2.66 percent on June 24, from a low of 1.61 percent on May 1, yields on inflation-indexed debt climbed even faster and further. As a result, the narrowing in the difference between yields of nominal Treasuries and TIPS, known as the break-even rate, showed that investors viewed inflation as less of a threat in the short term and thus were cutting the price they would pay for insurance against it, said Daniel Shackelford, a fixed-income portfolio manager at T. Rowe Price Group Inc. in Baltimore.

“Inflation expectations haven’t budged after three or four years of hyper-easing, and now we are looking at an expectation for a Fed that will become less accommodative,” said Shackelford, who runs the $496 million T. Rowe Price Inflation Protected Bond Fund. “It was sort of the worst news that the TIPS market could receive.”

Shackelford’s fund lost 6.8 percent this year, trailing 76 percent of similarly managed funds. It beat 86 percent over three years and 56 percent over five years, according to data compiled by Bloomberg.

TIPS funds fell an average of 7.2 percent from the end of April through June 28, more than double the 3.3 percent decline in the Barclays US Aggregate Index, a fixed-income benchmark, according to Michelle Canavan, a mutual-fund analyst at Chicago- based Morningstar Inc. who follows inflation-protected bond funds.

At Pimco Total Return, TIPS were the largest detractor from the performance during May, said Eric Jacobson, another Morningstar analyst, even though the fund’s holdings in nominal Treasuries were about 50 percent larger.

According to Jacobson, Pimco funds and accounts own about $100 billion of inflation-linked bonds, most of that in TIPS.

The total market value of TIPS outstanding is $869 billion, not including $111 billion that is held by the Fed, according to Paul Wynn, the portfolio manager for the $837 million Western Asset/Claymore Inflation-Linked Opportunities & Income Fund.

With such a large market share, it’s difficult for Gross and other Pimco managers to meaningfully change their positions without moving prices, said a former bond manager at the firm who requested anonymity. As a result, Gross must accept short-term volatility in the fund as the price of making long-term bets in the TIPS market, he said.