How to say careful as he was, he made an unexpected mistake. in Japanese

1)注意深no dictionary result, likely a conjigated verbno dictionary result, likely a conjigated verbか(ka) (prt) indicates question/indicates choice, doubt, etc.ったけれどもno dictionary result, likely a conjigated verbno dictionary result, likely a conjigated verb、(、) Japanese comma彼(kare) (ok) that , or something understood without naming it directly)/that person/over there/hey/eh?/thatは(ha) (int) indicating a subject/yes/indeed/well/ha!/what?/huh?/sighno dictionary result, likely a conjigated verbno dictionary result, likely a conjigated verbわ(wa) (prt) indicates emotion or admiration/adds a female middle aged feel at the end of a sentenceぬ(nu) (aux-v,suf) not/indicates completionミスミス(misu) (n,vs) mistake/error/failure/miss/mythを(wo) (prt) indicates direct object of action/indicates subject of causative expression/indicates an area traversed/indicates time over which action takes place/indicates point of departure or separation of action/indicates object of desire, like, hate,お(o) (int) oh!/polite prefix to the next wordか(ka) (prt) indicates question/indicates choice, doubt, etc.したした(shita) (n) did/a past form of the previous verb/tongue/tongue-like object/clapper/talon。(。) Japanese period "."    
chuuibukaka ttakeredomo 、 kareha omowa nu misu wookashita 。
Grammer form謙譲語 (Humble form)Humble form (kenjougo)
convays a sense of humility, commonly used by store employees, espessially in the service industry.
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