to enter with
suneiserchomai describes entering together with others, whether into a courtyard or into a boat.
The two verses show entering together with others: a disciple enters the high priest's courtyard with Jesus in John 18:15, while John 6:22 concerns whether Jesus entered the boat with his disciples.
Senses in use
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Enter together with others · dominant
The aorist active indicative singular form occurs in scenes of shared entry. In John 18:15 the APB renders that the other disciple "entered with Jesus into the courtyard of the high priest"; in John 6:22 it renders the crowd's observation that Jesus had not "entered the boat with his disciples."
In the Anselm Project Bible: The APB presents the action with "entered with" in both verses, specifying entry into the high priest's courtyard in John 18:15 and into a boat with the disciples in John 6:22. These phrases describe the clauses rather than establish a separate English rendering.