If the transmission or engine has never had an oil and filter change then its time. The color and clearness of the oil is an indication if it needs service. There is no reason what so ever to not change out dirty oil or filter for any reason.
Old crack pot idea's are bull. Also transmission flushed are expensive but it changes out the entire amount of fluid and takes away the mixing of old oil and new oil added. Other than that there is no reason not to if you have the money.
The filter will also need to be changed. Regardless of what you read the fluid if dark and dirty will need to be changed. On the rare occasions if the transmission is very dirty and you change the oil and filter.
The new filter can become clogged if you use a cleaner addictive. Simply change the filter again if you have problems. Nothing to it.
Maybe. I think the issue is completely undecided at this point but there have been an awful lot of reports of transmissions failing or otherwise misbehaving within a few weeks after changing the fluid for the first time in many miles. Honda transmissions often get harsh, even with genuine Honda ATF, if they get their first drain and fill late in life.
One chap in a Honda forum had an interesting observation: people tend to try a fluid change when their transmission is acting up and - lo and behold - the transmission fails soon afterward. My take is that the risk is not worth it.
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