I have activated tweet_mode=extended
It just doesn’t work on tweets that contain multiple media (mixed media)
Like this tweet:

1577730948547878912
Tweet has 3 media but shows only one

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API v1.1 is not currently being enhanced and will be retired in the future. Not all new features may be reflected in the older API.

Have you tried this same query with v2?

For example, for me:

twurl -j "/2/tweets/1577730948547878912?expansions=attachments.media_keys&tweet.fields=attachments"

{
  "data": {
    "id": "1577730948547878912",
    "edit_history_tweet_ids": [
      "1577730948547878912"
    ],
    "text": "@TwitterSupport What about combining video from “tweet video” + GIF + picture?\n\nLet’s try it. https://t.co/2pHq2zKyXP https://t.co/5w9nSAHVR2 https://t.co/zOtkZL29Yt",
    "attachments": {
      "media_keys": [
        "16_1577730941207941147",
        "3_1577730941207838721",
        "13_1577729188521545742"
      ]
    }
  },
  "includes": {
    "media": [
      {
        "media_key": "16_1577730941207941147",
        "type": "animated_gif"
      },
      {
        "media_key": "3_1577730941207838721",
        "type": "photo"
      },
      {
        "media_key": "13_1577729188521545742",
        "type": "video"
      }
    ]
  }
}
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