Possible Duplicate:
“I have been keeping ignoring you.”

The following sentence sounds odd to me, however I cannot think of any rules that would make its syntax incorrect:

"I would recommend considering upgrading to the latest version of the product"

What would be the correct way of communicating this statement?

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    This sentence is grammatically correct but stylistically a bit awkward because of the two words ending in "ing". You can make it smoother but not more correct by changing it to "I recommend that you consider upgrading..." – user21497 Jan 25 '13 at 0:07
  • Yes, I'd agree with that one 100%. It's playing by the rules, but it isn't winning. – Jon Hanna Jan 25 '13 at 0:11
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    What John said. Except I'll go further and say his answer to "I have been keeping ignoring you." pretty much fully covers both the reason why we don't like this form, and what the acceptable alternative is. In short, it's a dup. – FumbleFingers Jan 25 '13 at 0:21

It depends if you're recommending the consideration to upgrade or recommending to upgrade. The double gerund and "would" all smell of fluffing the sentence. When you're sure what you want to recommend:

"I recommend considering an upgrade to the latest version of the product"

"I recommend upgrading to the latest version of the product"

I'd only use the first version when talking to a corporate client, knowing that it would not be a simple matter to make the choice to upgrade.

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Your statement can be modified (in style) to convey your intended meaning as follows:

I would recommend considering an upgrade to the latest version of the product."

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That form is called a present participle aka gerund.

Participles are very interesting particles. They can be used to turn a verb into a noun, adjective or adverb.

e.g. past-completed participles as adjective or adverbs

  • Paint : The painted door.
  • Grow : A grown man.
  • Bless : Blessed are the meek. /* implied descriptee noun for descriptor blessed */
  • Deject: She was crying dejectedly.

e.g. present-continuous participles as adjectives or adverbs

  • Run: The running dogs.
  • Fly: Flying eagles.
  • Kill : The killing fields.
  • F*ck: The f*cking idiot.
  • Flail: She ran flailingly towards her lover.

The participle form of interest to your question is present-continuous participles' transforming a verb into a noun or a noun-phrase.

  • Paint, pass: Van Gogh's paintings became priceless after his passing away.
  • Closing : Closing the restaurant was depressing to her.
  • Run : {Running around the block} is a daily activity you should consider.
  • Go, rejoice: His going to school gave reason to his parents' rejoicing.
  • Transform: Participles' transforming verbs into nouns or noun-phrases is a very interesting feature.
  • Marry :

    Princess Diana's {marrying an Egyptian} had made the Palace very unhappy.

  • Consider:

    Princess Diana's {considering {marriage to an Egyptian}} had mortified the Palace.

  • Where {marriage to an Egyptian} = {marrying an Eyptian} :

    Princess Diana's {considering {marrying an Eyptian}} had mortified the Palace.

  • ...

    I would recommend {marrying an Eyptian} as the best way for her to escape from a stifled royal household.

  • The cascading of participles again:

    I would recommend {considering {marrying an Eyptian}} as the best way for her to mentally escape from a stifled royal household.

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  • Stifled and packaged by their boxed-up ideologies, there is someone persistently begrudging my mathematical treatment of English grammar. – Blessed Geek Jan 25 '13 at 2:39

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