diff --git a/src/together/lib/cli/api/beta/clusters/storage/retrieve.py b/src/together/lib/cli/api/beta/clusters/storage/retrieve.py
index 51379ea5..5349636c 100644
--- a/src/together/lib/cli/api/beta/clusters/storage/retrieve.py
+++ b/src/together/lib/cli/api/beta/clusters/storage/retrieve.py
@@ -1,7 +1,5 @@
 from __future__ import annotations
 
-from rich import print_json
-
 from together._utils._json import openapi_dumps
 from together.lib.cli.utils.config import CLIConfigParameter
 from together.lib.cli.utils._console import console
@@ -18,7 +16,7 @@ async def retrieve(
     request = config.client.beta.clusters.storage.retrieve(volume_id)
 
     if config.json:
-        print_json(openapi_dumps(await request).decode("utf-8"))
+        console.print_json(openapi_dumps(await request).decode("utf-8"))
         return
 
     storage = await show_loading_status("Retrieving storage volume...", request)
diff --git a/src/together/lib/cli/api/beta/jig/jig.py b/src/together/lib/cli/api/beta/jig/jig.py
index 26a91d13..a07a90ac 100644
--- a/src/together/lib/cli/api/beta/jig/jig.py
+++ b/src/together/lib/cli/api/beta/jig/jig.py
@@ -713,7 +713,7 @@ def deploy(
                 raise
 
         if detach or no_track:
-            console.print_json(json.dumps(response.model_dump()))
+            console.print_json(openapi_dumps(response).decode("utf-8"))
             return
 
         self.track(response)
@@ -931,9 +931,13 @@ def _print_cli_result(result: Any) -> None:
         return
     if isinstance(result, str):
         console.print(result)
-    elif hasattr(result, "json") and callable(result.json):
-        console.print_json(json.dumps(result.json()))
-    else:
+        return
+    if hasattr(result, "json") and callable(result.json):
+        console.print_json(openapi_dumps(result.json()).decode("utf-8"))
+        return
+    try:
+        console.print_json(openapi_dumps(result).decode("utf-8"))
+    except TypeError:
         console.print(str(result))
 
 
@@ -1222,7 +1226,7 @@ async def jig_volumes_list(
     data, next_cursor = mock_pagination(list_resp.data or [], cursor_field="id", cursor=after)
 
     if config.json:
-        console.print_json(openapi_dumps(list_resp).decode())
+        console.print_json(openapi_dumps(list_resp).decode("utf-8"))
         return
 
     EMPTY_MESSAGE = "You don't have any volumes yet. To create your first volume run:\n  [dim]-[/dim] [primary]tg beta jig volumes create[/primary]"
@@ -1253,7 +1257,14 @@ async def jig_volumes_describe(
     except NotFoundError:
         _jig_fail(f"Volume {name} not found")
     else:
-        console.print_json(openapi_dumps(vol).decode())
+        if config.json:
+            console.print_json(openapi_dumps(vol).decode("utf-8"))
+        else:
+            console.print(f"[bold dim]ID[/bold dim]         [blue]{vol.id or '—'}[/blue]")
+            console.print(f"[bold dim]Name[/bold dim]       [blue]{vol.name or '—'}[/blue]")
+            console.print(f"[bold dim]Created[/bold dim]     [blue]{vol.created_at or '—'}[/blue]")
+            console.print(f"[bold dim]Updated[/bold dim]     [blue]{vol.updated_at or '—'}[/blue]")
+            console.print(f"[bold dim]Version[/bold dim]      [blue]{vol.current_version!s}[/blue]")
 
 
 def dockerfile_cli(
diff --git a/src/together/lib/cli/api/endpoints/retrieve.py b/src/together/lib/cli/api/endpoints/retrieve.py
index 5228107f..35891984 100644
--- a/src/together/lib/cli/api/endpoints/retrieve.py
+++ b/src/together/lib/cli/api/endpoints/retrieve.py
@@ -1,9 +1,8 @@
 from __future__ import annotations
 
-from rich import print_json
-
 from together._utils._json import openapi_dumps
 from together.lib.cli.utils.config import CLIConfigParameter
+from together.lib.cli.utils._console import console
 from together.lib.cli.components.loader import show_loading_status
 from together.lib.cli.api.endpoints._utils import print_endpoint, handle_endpoint_api_errors
 
@@ -18,7 +17,7 @@ async def retrieve(
 
     endpoint = await show_loading_status("Loading endpoint...", config.client.endpoints.retrieve(endpoint_id))
     if config.json:
-        print_json(openapi_dumps(endpoint).decode("utf-8"))
+        console.print_json(openapi_dumps(endpoint).decode("utf-8"))
         return
 
     print_endpoint(endpoint)
diff --git a/src/together/lib/cli/api/evals/retrieve.py b/src/together/lib/cli/api/evals/retrieve.py
index 9b035268..34d947a3 100644
--- a/src/together/lib/cli/api/evals/retrieve.py
+++ b/src/together/lib/cli/api/evals/retrieve.py
@@ -3,6 +3,7 @@
 from typing import Annotated
 
 from cyclopts import Parameter
+from rich.markup import escape as escape_rich_markup
 
 from together._utils._json import openapi_dumps
 from together.lib.cli.utils.config import CLIConfigParameter
@@ -19,6 +20,11 @@ async def retrieve(
     response = await show_loading_status("Retrieving eval...", config.client.evals.retrieve(evaluation_id))
     if config.json:
         console.print_json(openapi_dumps(response).decode("utf-8"))
-    else:
-        # TODO: Add a pretty print for this
-        console.print_json(openapi_dumps(response).decode("utf-8"))
+        return
+
+    wid = response.workflow_id or evaluation_id
+    console.print(
+        f"[dim]Eval[/dim] [bold]{escape_rich_markup(str(wid))}[/bold] — "
+        f"[dim]status[/dim] [bold]{escape_rich_markup(str(response.status))}[/bold] — "
+        f"[dim]type[/dim] [bold]{escape_rich_markup(str(response.type))}[/bold]"
+    )
diff --git a/src/together/lib/cli/api/files/retrieve_content.py b/src/together/lib/cli/api/files/retrieve_content.py
index eb5b6ea1..ff52d538 100644
--- a/src/together/lib/cli/api/files/retrieve_content.py
+++ b/src/together/lib/cli/api/files/retrieve_content.py
@@ -2,12 +2,14 @@
 
 import os
 import sys
+import base64
 from typing import Optional, Annotated
 from pathlib import Path
 
 from cyclopts import Parameter, validators
 
 from together import AsyncTogether
+from together._utils._json import openapi_dumps
 from together.lib.cli.utils.config import CLIConfigParameter
 from together.lib.cli.utils._console import console
 from together.lib.cli.components.loader import show_loading_status
@@ -35,11 +37,23 @@ async def retrieve_content(
         console.print(f"[red]Invalid usage: Either --output <directory> or --stdout must be specified[/red]")
         sys.exit(1)
 
+    if stdout is True and output is not None:
+        console.print(f"[red]Invalid usage: --stdout and --output cannot be used together[/red]")
+        sys.exit(1)
+
     response = await show_loading_status("Retrieving file contents...", config.client.files.content(id=id))
 
     if stdout:
-        bytes = await response.read()
-        console.print(bytes.decode("utf-8"))
+        raw = await response.read()
+        if config.json:
+            try:
+                payload = {"id": id, "content": raw.decode("utf-8")}
+            except UnicodeDecodeError:
+                payload = {"id": id, "content_base64": base64.b64encode(raw).decode("ascii")}
+            console.print_json(openapi_dumps(payload).decode("utf-8"))
+        else:
+            console.print(raw.decode("utf-8"))
+        return
 
     if output is not None:
         os.makedirs(os.path.dirname(output) or ".", exist_ok=True)
@@ -49,4 +63,7 @@ async def retrieve_content(
         response = await config.client.files.content(id=id)
         await response.write_to_file(out_path)
 
-        console.print(f"File saved to [blue]{out_path}[/blue]")
+        if config.json:
+            console.print_json(openapi_dumps({"id": id, "path": str(out_path)}).decode("utf-8"))
+        else:
+            console.print(f"File saved to [blue]{out_path}[/blue]")
diff --git a/src/together/lib/cli/api/files/upload.py b/src/together/lib/cli/api/files/upload.py
index 13665053..85615054 100644
--- a/src/together/lib/cli/api/files/upload.py
+++ b/src/together/lib/cli/api/files/upload.py
@@ -2,7 +2,6 @@
 
 import os
 import sys
-import json as json_lib
 from typing import Optional, Annotated, cast, get_args
 from pathlib import Path
 
@@ -33,7 +32,7 @@ async def upload(
         report = check_file(file)
         if report["is_check_passed"] is False:
             if config.json:
-                console.print_json(json_lib.dumps(report))
+                console.print_json(openapi_dumps(report).decode("utf-8"))
             else:
                 console.print(f"[red]❌ {escape_rich_markup(str(report['message']))}[/red]")
 
diff --git a/src/together/lib/cli/api/fine_tuning/cancel.py b/src/together/lib/cli/api/fine_tuning/cancel.py
index 67a72d1a..9f299edf 100644
--- a/src/together/lib/cli/api/fine_tuning/cancel.py
+++ b/src/together/lib/cli/api/fine_tuning/cancel.py
@@ -37,7 +37,7 @@ async def cancel(
         confirm_response = input(f"Do you want to cancel job {fine_tune_id}? [y/N]")
         if "y" not in confirm_response.lower():
             if config.json:
-                console.print_json('{"status": "Cancel not submitted"}')
+                console.print_json(openapi_dumps({"status": "Cancel not submitted"}).decode("utf-8"))
             else:
                 console.print("Cancel not submitted")
             return
diff --git a/src/together/lib/cli/api/fine_tuning/list.py b/src/together/lib/cli/api/fine_tuning/list.py
index 107422a4..ed747f64 100644
--- a/src/together/lib/cli/api/fine_tuning/list.py
+++ b/src/together/lib/cli/api/fine_tuning/list.py
@@ -2,8 +2,6 @@
 
 from datetime import datetime, timezone
 
-from rich import print_json
-
 from together.lib.utils import finetune_price_to_dollars
 from together._utils._json import openapi_dumps
 from together.lib.utils.tools import format_datetime
@@ -46,7 +44,7 @@ async def list(
     fine_tunings_to_display, next_cursor = mock_pagination(response.data, cursor_field="id", cursor=after)
 
     if config.json:
-        print_json(openapi_dumps(fine_tunings_to_display).decode("utf-8"))
+        console.print_json(openapi_dumps(fine_tunings_to_display).decode("utf-8"))
         return
 
     EMPTY_MESSAGE = "You don't have any finetuned models yet. To fine tune your first model run:\n  [dim]-[/dim] [primary]tg ft create[/primary]"
diff --git a/src/together/lib/cli/api/telemetry/disable.py b/src/together/lib/cli/api/telemetry/disable.py
index 837905d5..c094e040 100644
--- a/src/together/lib/cli/api/telemetry/disable.py
+++ b/src/together/lib/cli/api/telemetry/disable.py
@@ -1,16 +1,25 @@
 from __future__ import annotations
 
+from together._utils._json import openapi_dumps
 from together.lib.cli._track_cli import (
     load_telemetry_config,
     save_telemetry_config,
     telemetry_config_path,
 )
+from together.lib.cli.utils.config import CLIConfigParameter
 from together.lib.cli.utils._console import console
 
 
-def disable() -> None:
+def disable(
+    *,
+    config: CLIConfigParameter,
+) -> None:
     """Explicitly Disable telemetry"""
     cfg = load_telemetry_config()
     cfg["telemetry_enabled"] = False
     save_telemetry_config(cfg)
-    console.print(f"Telemetry: [blue]Disabled[/blue]\n[dim](saved to {telemetry_config_path()})[/dim]")
+    path = telemetry_config_path()
+    if config.json:
+        console.print_json(openapi_dumps({"telemetry_enabled": False, "saved_to": str(path)}).decode("utf-8"))
+        return
+    console.print(f"Telemetry: [blue]Disabled[/blue]\n[dim](saved to {path})[/dim]")
diff --git a/src/together/lib/cli/api/telemetry/enable.py b/src/together/lib/cli/api/telemetry/enable.py
index c1e4fc1c..ef1e38d3 100644
--- a/src/together/lib/cli/api/telemetry/enable.py
+++ b/src/together/lib/cli/api/telemetry/enable.py
@@ -1,16 +1,25 @@
 from __future__ import annotations
 
+from together._utils._json import openapi_dumps
 from together.lib.cli._track_cli import (
     load_telemetry_config,
     save_telemetry_config,
     telemetry_config_path,
 )
+from together.lib.cli.utils.config import CLIConfigParameter
 from together.lib.cli.utils._console import console
 
 
-def enable() -> None:
+def enable(
+    *,
+    config: CLIConfigParameter,
+) -> None:
     """Enable telemetry"""
     cfg = load_telemetry_config()
     cfg["telemetry_enabled"] = True
     save_telemetry_config(cfg)
-    console.print(f"Telemetry: [blue]Enabled[/blue]\n[dim](saved to {telemetry_config_path()})[/dim]")
+    path = telemetry_config_path()
+    if config.json:
+        console.print_json(openapi_dumps({"telemetry_enabled": True, "saved_to": str(path)}).decode("utf-8"))
+        return
+    console.print(f"Telemetry: [blue]Enabled[/blue]\n[dim](saved to {path})[/dim]")
diff --git a/src/together/lib/cli/api/telemetry/status.py b/src/together/lib/cli/api/telemetry/status.py
index 4cc1b3bd..8fbfd743 100644
--- a/src/together/lib/cli/api/telemetry/status.py
+++ b/src/together/lib/cli/api/telemetry/status.py
@@ -1,16 +1,36 @@
+from __future__ import annotations
+
+from together._utils._json import openapi_dumps
 from together.lib.cli._track_cli import (
     _env_telemetry_disabled,
     _config_telemetry_disabled,
 )
+from together.lib.cli.utils.config import CLIConfigParameter
 from together.lib.cli.utils._console import console
 
 
-def status() -> None:
+def status(
+    *,
+    config: CLIConfigParameter,
+) -> None:
     """Check to see if telemetry is enabled or disabled."""
-    if _config_telemetry_disabled():
+    by_config = _config_telemetry_disabled()
+    by_env = _env_telemetry_disabled()
+
+    if config.json:
+        if by_config:
+            payload = {"telemetry": "disabled", "reason": "config_file"}
+        elif by_env:
+            payload = {"telemetry": "disabled", "reason": "environment"}
+        else:
+            payload = {"telemetry": "enabled"}
+        console.print_json(openapi_dumps(payload).decode("utf-8"))
+        return
+
+    if by_config:
         console.print("Telemetry: [blue]Disabled[/blue]")
         return
-    if _env_telemetry_disabled():
+    if by_env:
         console.print("Telemetry: [blue]Disabled[/blue] [dim](via environment variable)[/dim]")
         return
     console.print("Telemetry: [blue]Enabled[/blue]")
diff --git a/tests/cli/test_analytics.py b/tests/cli/test_analytics.py
index 32c194a9..2c85672d 100644
--- a/tests/cli/test_analytics.py
+++ b/tests/cli/test_analytics.py
@@ -3,6 +3,7 @@
 from __future__ import annotations
 
 import json
+import subprocess
 from pathlib import Path
 
 import pytest
@@ -46,6 +47,13 @@ def test_telemetry_enable_then_status(isolated_cli_config: Path, cli_runner: Cli
     assert "Enabled" in r2.output
 
 
+def test_telemetry_json_mode_pipes_to_jq(cli_runner: CliRunner) -> None:
+    r = cli_runner.invoke(["telemetry", "status", "--json"])
+    assert r.exit_code == 0
+    jq = subprocess.run(["jq"], input=r.out_out, capture_output=True, text=True)
+    assert jq.returncode == 0, jq.stderr
+
+
 def test_telemetry_status_shows_env_opt_out(
     isolated_cli_config: Path,
     monkeypatch: pytest.MonkeyPatch,
diff --git a/tests/cli/test_evals.py b/tests/cli/test_evals.py
index af7d8c10..319a95a6 100644
--- a/tests/cli/test_evals.py
+++ b/tests/cli/test_evals.py
@@ -48,9 +48,10 @@ class TestEvalsRetrieveAndStatus:
     @pytest.mark.respx(base_url=base_url)
     def test_retrieve(self, respx_mock: MockRouter, cli_runner: CliRunner) -> None:
         respx_mock.get("/evaluation/eval-wf-1").mock(return_value=httpx.Response(200, json=_EVAL_JOB))
-        result = cli_runner.invoke(["evals", "retrieve", "eval-wf-1"])
+        result = cli_runner.invoke(["evals", "retrieve", "eval-wf-1", "--json"])
         assert result.exit_code == 0
-        assert json.loads(result.output)["workflow_id"] == "eval-wf-1"
+        payload = json.loads(result.out_out.lstrip("\n"))
+        assert payload["workflow_id"] == "eval-wf-1"
 
     @pytest.mark.respx(base_url=base_url)
     def test_status(self, respx_mock: MockRouter, cli_runner: CliRunner) -> None:
diff --git a/tests/cli/test_files.py b/tests/cli/test_files.py
index bfa7356a..dd823d2b 100644
--- a/tests/cli/test_files.py
+++ b/tests/cli/test_files.py
@@ -147,20 +147,15 @@ def test_specifying_stdout(self, respx_mock: MockRouter, cli_runner: CliRunner)
         respx_mock.get("/files/file-1/content").mock(return_value=httpx.Response(200, content=b"stdout-bytes"))
         result = cli_runner.invoke(["files", "retrieve-content", "file-1", "--stdout"])
         assert result.exit_code == 0
-        assert result.output == "stdout-bytes\n"
+        # Rich loading status may leave a leading newline before body output
+        assert result.output.lstrip("\n") == "stdout-bytes\n"
 
-    @pytest.mark.respx(base_url=base_url)
-    def test_specifying_both_output_and_stdout(
-        self, respx_mock: MockRouter, tmp_path: Path, cli_runner: CliRunner
-    ) -> None:
-        respx_mock.get("/files/file-1/content").mock(return_value=httpx.Response(200, content=b"to-stdout"))
+    def test_specifying_both_output_and_stdout(self, tmp_path: Path, cli_runner: CliRunner) -> None:
         out = tmp_path / "should-not-exist.bin"
         result = cli_runner.invoke(["files", "retrieve-content", "file-1", "--stdout", "--output", str(out)])
-        assert result.exit_code == 0
-        assert result.output.startswith("to-stdout\n")
-        assert "File saved to" in result.output
-        assert str(out) in result.output.replace("\n", "")
-        assert out.exists()
+        assert result.exit_code == 1
+        assert "cannot be used together" in result.output
+        assert not out.exists()
 
 
 class TestFilesUpload: