Money can’t buy you love. Returning billions of dollars to investors since July 2004 has failed to breathe life into Microsoft’s shares. Will the company try buying growth instead?

One obvious target is Yahoo. The internet portal sits squarely in the hole Microsoft needs to fill. In a stroke, it would narrow Google’s commanding lead in internet search. Microsoft/Yahoo would have 42 per cent of US queries according to Comscore, compared with Google’s 44 per cent. Yahoo has a more developed network of advertisers than Microsoft to generate search revenue. Meanwhile, Yahoo would bring market leadership in display advertising and combining with Microsoft would create a powerful e-mail and instant messaging user base. Conceptually, Yahoo’s media savvy and ability to woo internet traffic would complement Microsoft’s technology expertise. It would give Microsoft a busy shop window for new software services where MSN, its own creation, has struggled.

The practicalities are trickier. Regulators would hardly welcome Microsoft, of all companies, creating a near-duopoly in internet search and buying a major position in other services. There would be huge execution risk. While Microsoft’s and Yahoo’s skills are complementary, their cultures are very different. Trying to mesh them together could cause employee defections and big management headaches. Yahoo users might also go elsewhere.

Finally, there is valuation. There would be cost savings from combining overlapping businesses. But any deal would really be about creating a new growth platform for Microsoft. Given the inherent uncertainty of revenue synergies, paying a big premium for Yahoo would be a gamble. On top of everything, Microsoft lacks experience of big acquisitions. For now, Microsoft will keep spending aggressively on its web strategy. But, if that falters, its excessive cash pile and prodigious cash flow might make the temptation to buy new users irresistible.