Transcription not identifying multiple audio files

This is a limitation of the current text-based editing workflow—Premiere will only display the transcript from overlapping clips if they are channels from the same file.

Here are a couple of workarounds you can try:

Combine your files into one new file

1. Select your clips in the Project panel and then choose Clip > Merge Clips to combine them into one clip.
2. Select the merged clip and choose File > Export and choose a format that supports multichannel audio (like WAV or Quicktime).
3. Go to Basic Audio Settings, click More, scroll down to the bottom, and choose the maximum number of audio channels.
4. Import this new file into your project and delete the Merged Clip.
5. Transcribe it and use this for editing.

Delete the pauses in the first file

1. In your timeline, if you have a clip on Track 1 and another on Track 2, lock Track 2.
2. In the Transcript tab of the Text panel, click the Transcript View Options button in the bottom right.
3. Increase the Minimum Pause Length to something that would indicate that the other person is speaking (you can type a number higher than the slider) and click Save.
4. Click the Filter icon and choose Pauses.
5. Click Delete, choose Lift, and then click Delete All.
6. This will delete a gap in Clip 1 whenever someone on Clip 2 is speaking, which will enable the transcript from Clip 2 in the Text panel.