diff --git a/src/cleveragents/cli.py b/src/cleveragents/cli.py
index 69eac2947..ff836310c 100644
--- a/src/cleveragents/cli.py
+++ b/src/cleveragents/cli.py
@@ -981,23 +981,85 @@ def clear_context(name: str, context_dir: Optional[Path]) -> None:
 
 
 @context.command("delete")
-@click.argument("name")
+@click.argument("name", required=False)
 @click.option(
     "--context-dir",
     type=click.Path(file_okay=False, dir_okay=True, path_type=Path),
     help="Directory where contexts are stored.",
 )
-@click.confirmation_option(prompt="Are you sure you want to delete this context?")
-def delete_context(name: str, context_dir: Optional[Path]) -> None:
-    """Delete a context and all its data."""
+@click.option(
+    "--all",
+    is_flag=True,
+    help="Delete all contexts.",
+)
+@click.option(
+    "--yes",
+    "-y",
+    is_flag=True,
+    help="Skip confirmation prompt.",
+)
+def delete_context(name: Optional[str], context_dir: Optional[Path], all: bool, yes: bool) -> None:
+    """Delete a context and all its data, or delete all contexts with --all."""
     try:
-        ctx_manager = ContextManager(name, context_dir)
-        if not ctx_manager.exists():
-            click.echo(f"Context '{name}' does not exist.", err=True)
+        # Validate arguments
+        if all and name:
+            click.echo("Error: Cannot specify NAME when using --all flag.", err=True)
             sys.exit(1)
 
-        ctx_manager.delete()
-        click.echo(f"Context '{name}' has been deleted.")
+        if not all and not name:
+            click.echo("Error: Must specify NAME or use --all flag.", err=True)
+            sys.exit(1)
+
+        if all:
+            # Delete all contexts
+            contexts = ContextManager.list_contexts(context_dir)
+
+            if not contexts:
+                click.echo("No contexts found.")
+                return
+
+            # Show what will be deleted
+            click.echo(f"Found {len(contexts)} context(s) to delete:")
+            for ctx in contexts:
+                click.echo(f"  - {ctx}")
+
+            # Confirmation prompt (unless --yes is provided)
+            if not yes:
+                if not click.confirm("Are you sure you want to delete ALL contexts?"):
+                    click.echo("Operation cancelled.")
+                    return
+
+            # Delete all contexts
+            deleted_count = 0
+            failed_count = 0
+            for ctx_name in contexts:
+                try:
+                    ctx_manager = ContextManager(ctx_name, context_dir)
+                    ctx_manager.delete()
+                    deleted_count += 1
+                except Exception as e:  # pylint: disable=broad-exception-caught
+                    click.echo(f"Failed to delete context '{ctx_name}': {e}", err=True)
+                    failed_count += 1
+
+            click.echo(f"Deleted {deleted_count} context(s).")
+            if failed_count > 0:
+                click.echo(f"Failed to delete {failed_count} context(s).", err=True)
+        else:
+            # Delete single context
+            assert name is not None  # mypy type narrowing: guaranteed by validation above
+            ctx_manager = ContextManager(name, context_dir)
+            if not ctx_manager.exists():
+                click.echo(f"Context '{name}' does not exist.", err=True)
+                sys.exit(1)
+
+            # Confirmation prompt (unless --yes is provided)
+            if not yes:
+                if not click.confirm(f"Are you sure you want to delete context '{name}'?"):
+                    click.echo("Operation cancelled.")
+                    return
+
+            ctx_manager.delete()
+            click.echo(f"Context '{name}' has been deleted.")
     except Exception as e:  # pylint: disable=broad-exception-caught
         click.echo(f"Error: {e}", err=True)
         sys.exit(1)
diff --git a/src/cleveragents/context_manager.py b/src/cleveragents/context_manager.py
index 623f06475..3a874d3b8 100644
--- a/src/cleveragents/context_manager.py
+++ b/src/cleveragents/context_manager.py
@@ -227,8 +227,20 @@ class ContextManager:
 
         contexts = []
         for path in base_dir.iterdir():
-            if path.is_dir() and (path / "messages.json").exists():
-                contexts.append(path.name)
+            try:
+                if path.is_dir():
+                    # Try to check if messages.json exists, but if we can't access it
+                    # (due to permissions), assume it's a context directory anyway
+                    try:
+                        if (path / "messages.json").exists():
+                            contexts.append(path.name)
+                    except (PermissionError, OSError):
+                        # Can't access the directory contents, but it might be a context
+                        # Include it anyway and let deletion handle the error
+                        contexts.append(path.name)
+            except (PermissionError, OSError):
+                # Can't even check if it's a directory, skip it
+                continue
 
         return sorted(contexts)
 
diff --git a/tests/features/context_delete_all_yes.feature b/tests/features/context_delete_all_yes.feature
new file mode 100644
index 000000000..fa0c2ecb7
--- /dev/null
+++ b/tests/features/context_delete_all_yes.feature
@@ -0,0 +1,86 @@
+Feature: Context Delete with --all and --yes Flags
+  As a user of CleverAgents
+  I want to delete contexts individually or in bulk with confirmation control
+  So that I can efficiently manage my stored conversation contexts
+
+  Background:
+    Given I have a temporary test directory for contexts
+
+  Scenario: Delete single context with --yes bypasses confirmation
+    Given I have a context "test-context-1" in the test directory
+    When I run CLI command "context delete test-context-1 --yes" with test context dir
+    Then the command should succeed
+    And the context "test-context-1" should not exist
+
+  Scenario: Delete single context without --yes prompts for confirmation
+    Given I have a context "test-context-2" in the test directory
+    When I run CLI command "context delete test-context-2" with test context dir and answer "y"
+    Then the command should succeed
+    And the context "test-context-2" should not exist
+
+  Scenario: Delete single context - cancel confirmation
+    Given I have a context "test-context-3" in the test directory
+    When I run CLI command "context delete test-context-3" with test context dir and answer "n"
+    Then the command should be cancelled
+    And the context "test-context-3" should still exist
+
+  Scenario: Delete all contexts with --all --yes bypasses confirmation
+    Given I have contexts "ctx-a", "ctx-b", "ctx-c" in the test directory
+    When I run CLI command "context delete --all --yes" with test context dir
+    Then the command should succeed
+    And all contexts should be deleted
+    And the output should show "Deleted 3 context(s)"
+
+  Scenario: Delete all contexts with --all prompts for confirmation
+    Given I have contexts "ctx-d", "ctx-e" in the test directory
+    When I run CLI command "context delete --all" with test context dir and answer "y"
+    Then the command should succeed
+    And all contexts should be deleted
+    And the output should list all contexts before deletion
+
+  Scenario: Delete all contexts - cancel confirmation
+    Given I have contexts "ctx-f", "ctx-g" in the test directory
+    When I run CLI command "context delete --all" with test context dir and answer "n"
+    Then the command should be cancelled
+    And the contexts "ctx-f", "ctx-g" should still exist
+
+  Scenario: Error when both NAME and --all provided
+    When I run CLI command "context delete test-context --all" with test context dir
+    Then the command should fail with error "Cannot specify NAME when using --all flag"
+
+  Scenario: Error when neither NAME nor --all provided
+    When I run CLI command "context delete" with test context dir
+    Then the command should fail with error "Must specify NAME or use --all flag"
+
+  Scenario: Delete all when no contexts exist
+    Given the test context directory is empty
+    When I run CLI command "context delete --all --yes" with test context dir
+    Then the command should succeed
+    And the output should show "No contexts found"
+
+  Scenario: Delete single non-existent context
+    When I run CLI command "context delete non-existent --yes" with test context dir
+    Then the command should fail
+    And the output should show "does not exist"
+
+  Scenario: Delete all contexts with partial failures
+    Given I have contexts "ctx-h", "ctx-i" in the test directory
+    And context "ctx-i" directory is made read-only
+    When I run CLI command "context delete --all --yes" with test context dir
+    Then the command should succeed
+    And the output should show deleted count
+    And the output should show failed count
+
+  Scenario: Delete all shows context list before confirmation
+    Given I have contexts "alpha", "beta", "gamma" in the test directory
+    When I run CLI command "context delete --all" with test context dir and capture output
+    Then the output should contain "Found 3 context(s) to delete"
+    And the output should contain "alpha"
+    And the output should contain "beta"
+    And the output should contain "gamma"
+
+  Scenario: Using -y as shorthand for --yes
+    Given I have a context "test-short-yes" in the test directory
+    When I run CLI command "context delete test-short-yes -y" with test context dir
+    Then the command should succeed
+    And the context "test-short-yes" should not exist
diff --git a/tests/features/steps/context_delete_all_yes_steps.py b/tests/features/steps/context_delete_all_yes_steps.py
new file mode 100644
index 000000000..f2fe8f469
--- /dev/null
+++ b/tests/features/steps/context_delete_all_yes_steps.py
@@ -0,0 +1,247 @@
+"""Step definitions for Context Delete with --all and --yes flags."""
+
+import json
+import os
+import subprocess
+import tempfile
+from pathlib import Path
+
+from behave import given, then, when
+from behave.runner import Context
+
+
+@given('I have a context "{name}" in the test directory')
+def step_have_context_in_test_dir(context: Context, name: str) -> None:
+    """Create a single context in the test directory."""
+    if not hasattr(context, "context_dir"):
+        context.temp_dir = tempfile.mkdtemp(prefix="cleveragents_test_")
+        context.context_dir = Path(context.temp_dir) / "contexts"
+        context.context_dir.mkdir(parents=True, exist_ok=True)
+
+    # Create a simple context structure
+    ctx_dir = context.context_dir / name
+    ctx_dir.mkdir(parents=True, exist_ok=True)
+
+    # Create the standard context files
+    (ctx_dir / "messages.json").write_text("[]")
+    (ctx_dir / "metadata.json").write_text("{}")
+    (ctx_dir / "state.json").write_text("{}")
+    (ctx_dir / "global_context.json").write_text("{}")
+
+
+@given('I have contexts "{names}" in the test directory')
+def step_have_multiple_contexts_in_test_dir(context: Context, names: str) -> None:
+    """Create multiple contexts in the test directory."""
+    if not hasattr(context, "context_dir"):
+        context.temp_dir = tempfile.mkdtemp(prefix="cleveragents_test_")
+        context.context_dir = Path(context.temp_dir) / "contexts"
+        context.context_dir.mkdir(parents=True, exist_ok=True)
+
+    # Parse the comma-separated names
+    context_names = [name.strip().strip('"') for name in names.split(",")]
+
+    # Create each context
+    for name in context_names:
+        ctx_dir = context.context_dir / name
+        ctx_dir.mkdir(parents=True, exist_ok=True)
+
+        # Create the standard context files
+        (ctx_dir / "messages.json").write_text("[]")
+        (ctx_dir / "metadata.json").write_text("{}")
+        (ctx_dir / "state.json").write_text("{}")
+        (ctx_dir / "global_context.json").write_text("{}")
+
+
+@given("the test context directory is empty")
+def step_empty_test_context_dir(context: Context) -> None:
+    """Ensure the test context directory is empty."""
+    if not hasattr(context, "context_dir"):
+        context.temp_dir = tempfile.mkdtemp(prefix="cleveragents_test_")
+        context.context_dir = Path(context.temp_dir) / "contexts"
+        context.context_dir.mkdir(parents=True, exist_ok=True)
+
+    # Directory already empty since we just created it
+
+
+@given('context "{name}" directory is made read-only')
+def step_make_context_readonly(context: Context, name: str) -> None:
+    """Make a context directory read-only to simulate failure."""
+    ctx_dir = context.context_dir / name
+    if ctx_dir.exists():
+        # Make directory read-only
+        os.chmod(ctx_dir, 0o444)
+        # Track this for cleanup
+        if not hasattr(context, "readonly_dirs"):
+            context.readonly_dirs = []
+        context.readonly_dirs.append(ctx_dir)
+
+
+@when('I run CLI command "{command}" with test context dir')
+def step_run_cli_with_test_context_dir(context: Context, command: str) -> None:
+    """Run a CLI command with the test context directory."""
+    # Parse command and add --context-dir
+    cmd_parts = ["python", "-m", "cleveragents"] + command.split()
+    cmd_parts.extend(["--context-dir", str(context.context_dir)])
+
+    # Run the command
+    result = subprocess.run(cmd_parts, capture_output=True, text=True, cwd="/app")
+
+    context.cli_result = result
+    context.cli_stdout = result.stdout
+    context.cli_stderr = result.stderr
+    context.cli_returncode = result.returncode
+
+
+@when('I run CLI command "{command}" with test context dir and answer "{answer}"')
+def step_run_cli_with_answer(context: Context, command: str, answer: str) -> None:
+    """Run a CLI command with the test context directory and provide input."""
+    # Parse command and add --context-dir
+    cmd_parts = ["python", "-m", "cleveragents"] + command.split()
+    cmd_parts.extend(["--context-dir", str(context.context_dir)])
+
+    # Run the command with input
+    result = subprocess.run(cmd_parts, input=answer + "\n", capture_output=True, text=True, cwd="/app")
+
+    context.cli_result = result
+    context.cli_stdout = result.stdout
+    context.cli_stderr = result.stderr
+    context.cli_returncode = result.returncode
+
+
+@when('I run CLI command "{command}" with test context dir and capture output')
+def step_run_cli_and_capture_output(context: Context, command: str) -> None:
+    """Run a CLI command with the test context directory and capture all output."""
+    # Parse command and add --context-dir
+    cmd_parts = ["python", "-m", "cleveragents"] + command.split()
+    cmd_parts.extend(["--context-dir", str(context.context_dir)])
+
+    # Run the command (it will wait for input but we won't provide it to capture the output)
+    # We'll use a short timeout to avoid hanging
+    try:
+        result = subprocess.run(cmd_parts, input="n\n", capture_output=True, text=True, timeout=5, cwd="/app")
+        context.cli_result = result
+        context.cli_stdout = result.stdout
+        context.cli_stderr = result.stderr
+        context.cli_returncode = result.returncode
+    except subprocess.TimeoutExpired as e:
+        context.cli_stdout = e.stdout.decode() if e.stdout else ""
+        context.cli_stderr = e.stderr.decode() if e.stderr else ""
+        context.cli_returncode = -1
+
+
+# Note: "the command should succeed" and "the command should fail" are already defined in cli_steps.py
+
+
+@then("the command should be cancelled")
+def step_command_should_be_cancelled(context: Context) -> None:
+    """Verify the command was cancelled."""
+    assert "cancelled" in context.cli_stdout.lower() or "cancelled" in context.cli_stderr.lower(), (
+        f"Command was not cancelled\n" f"stdout: {context.cli_stdout}\n" f"stderr: {context.cli_stderr}"
+    )
+
+
+@then('the command should fail with error "{error_text}"')
+def step_command_should_fail_with_error(context: Context, error_text: str) -> None:
+    """Verify the command failed with specific error message."""
+    assert context.cli_returncode != 0, (
+        f"Command succeeded unexpectedly\n" f"stdout: {context.cli_stdout}\n" f"stderr: {context.cli_stderr}"
+    )
+
+    combined_output = context.cli_stdout + context.cli_stderr
+    assert error_text in combined_output, (
+        f"Expected error message not found: {error_text}\n"
+        f"stdout: {context.cli_stdout}\n"
+        f"stderr: {context.cli_stderr}"
+    )
+
+
+@then('the context "{name}" should not exist')
+def step_context_should_not_exist(context: Context, name: str) -> None:
+    """Verify a context does not exist."""
+    ctx_dir = context.context_dir / name
+    assert not ctx_dir.exists(), f"Context '{name}' still exists at {ctx_dir}"
+
+
+@then('the context "{name}" should still exist')
+def step_context_should_still_exist(context: Context, name: str) -> None:
+    """Verify a context still exists."""
+    ctx_dir = context.context_dir / name
+    assert ctx_dir.exists(), f"Context '{name}' does not exist at {ctx_dir}"
+
+
+@then("all contexts should be deleted")
+def step_all_contexts_deleted(context: Context) -> None:
+    """Verify all contexts were deleted."""
+    # List all subdirectories in the context directory
+    if context.context_dir.exists():
+        contexts = [d for d in context.context_dir.iterdir() if d.is_dir()]
+        assert len(contexts) == 0, f"Found {len(contexts)} contexts still present: {[c.name for c in contexts]}"
+
+
+@then('the contexts "{names}" should still exist')
+def step_contexts_should_still_exist(context: Context, names: str) -> None:
+    """Verify specific contexts still exist."""
+    context_names = [name.strip().strip('"') for name in names.split(",")]
+
+    for name in context_names:
+        ctx_dir = context.context_dir / name
+        assert ctx_dir.exists(), f"Context '{name}' does not exist at {ctx_dir}"
+
+
+@then('the output should show "{text}"')
+def step_output_should_show(context: Context, text: str) -> None:
+    """Verify the output contains specific text."""
+    combined_output = context.cli_stdout + context.cli_stderr
+    assert text in combined_output, (
+        f"Expected text not found in output: {text}\n" f"stdout: {context.cli_stdout}\n" f"stderr: {context.cli_stderr}"
+    )
+
+
+@then("the output should show deleted count")
+def step_output_shows_deleted_count(context: Context) -> None:
+    """Verify the output shows deleted count."""
+    combined_output = context.cli_stdout + context.cli_stderr
+    assert "Deleted" in combined_output and "context" in combined_output, (
+        f"Deleted count not found in output\n" f"stdout: {context.cli_stdout}\n" f"stderr: {context.cli_stderr}"
+    )
+
+
+@then("the output should show failed count")
+def step_output_shows_failed_count(context: Context) -> None:
+    """Verify the output shows failed count."""
+    combined_output = context.cli_stdout + context.cli_stderr
+    assert "Failed" in combined_output, (
+        f"Failed count not found in output\n" f"stdout: {context.cli_stdout}\n" f"stderr: {context.cli_stderr}"
+    )
+
+
+# Note: "the output should contain" is already defined in cli_steps.py as "the output should contain '{expected_text}'"
+
+
+@then("the output should list all contexts before deletion")
+def step_output_lists_contexts_before_deletion(context: Context) -> None:
+    """Verify the output lists contexts before deletion."""
+    combined_output = context.cli_stdout + context.cli_stderr
+    assert "Found" in combined_output and "to delete" in combined_output, (
+        f"Context list not found in output\n" f"stdout: {context.cli_stdout}\n" f"stderr: {context.cli_stderr}"
+    )
+
+
+def after_scenario(context, scenario):
+    """Clean up after each scenario."""
+    # Restore permissions on read-only directories
+    if hasattr(context, "readonly_dirs"):
+        for dir_path in context.readonly_dirs:
+            try:
+                os.chmod(dir_path, 0o755)
+            except Exception:
+                pass
+
+    # Clean up temp directory
+    if hasattr(context, "temp_dir"):
+        import shutil
+
+        try:
+            shutil.rmtree(context.temp_dir)
+        except Exception:
+            pass
diff --git a/tests/integration/context_delete_all_yes_test.robot b/tests/integration/context_delete_all_yes_test.robot
new file mode 100644
index 000000000..e9966dbc0
--- /dev/null
+++ b/tests/integration/context_delete_all_yes_test.robot
@@ -0,0 +1,318 @@
+*** Settings ***
+Documentation     Integration tests for context delete with --all and --yes flags
+Library           Process
+Library           OperatingSystem
+Library           String
+Library           DateTime
+Suite Setup       Setup Test Environment
+Suite Teardown    Cleanup Test Environment
+
+*** Variables ***
+${SIMPLE_CONFIG}            tests/fixtures/simple_echo_config.yaml
+${CONTEXT_DIR}              ${TEMPDIR}/test_contexts_delete_all_yes
+${UNIQUE_ID}                ${EMPTY}
+${TEMP}                     ${EMPTY}
+
+*** Test Cases ***
+Test Delete Single Context With Yes Flag
+    [Documentation]    Test context delete with --yes bypasses confirmation
+    ${context_name} =    Set Variable    delete_yes_${UNIQUE_ID}
+
+    # Create context
+    Run Process    python    -m    cleveragents    run
+    ...    -c    ${SIMPLE_CONFIG}
+    ...    --context    ${context_name}
+    ...    --context-dir    ${CONTEXT_DIR}
+    ...    --unsafe
+    ...    -p    "test message"
+
+    Directory Should Exist    ${CONTEXT_DIR}/${context_name}
+
+    # Delete it with --yes flag
+    ${result} =    Run Process    python    -m    cleveragents    context    delete
+    ...    ${context_name}
+    ...    --context-dir    ${CONTEXT_DIR}
+    ...    --yes
+
+    Should Be Equal As Integers    ${result.rc}    0
+    Directory Should Not Exist    ${CONTEXT_DIR}/${context_name}
+    Should Contain    ${result.stdout}    deleted
+
+Test Delete Single Context With Short Yes Flag
+    [Documentation]    Test context delete with -y shorthand flag
+    ${context_name} =    Set Variable    delete_short_${UNIQUE_ID}
+
+    # Create context
+    Run Process    python    -m    cleveragents    run
+    ...    -c    ${SIMPLE_CONFIG}
+    ...    --context    ${context_name}
+    ...    --context-dir    ${CONTEXT_DIR}
+    ...    --unsafe
+    ...    -p    "test message"
+
+    Directory Should Exist    ${CONTEXT_DIR}/${context_name}
+
+    # Delete it with -y flag
+    ${result} =    Run Process    python    -m    cleveragents    context    delete
+    ...    ${context_name}
+    ...    --context-dir    ${CONTEXT_DIR}
+    ...    -y
+
+    Should Be Equal As Integers    ${result.rc}    0
+    Directory Should Not Exist    ${CONTEXT_DIR}/${context_name}
+
+Test Delete Single Context With Confirmation Accept
+    [Documentation]    Test context delete with confirmation accepted
+    ${context_name} =    Set Variable    delete_confirm_${UNIQUE_ID}
+
+    # Create context
+    Run Process    python    -m    cleveragents    run
+    ...    -c    ${SIMPLE_CONFIG}
+    ...    --context    ${context_name}
+    ...    --context-dir    ${CONTEXT_DIR}
+    ...    --unsafe
+    ...    -p    "test message"
+
+    Directory Should Exist    ${CONTEXT_DIR}/${context_name}
+
+    # Delete with confirmation (answer 'y')
+    ${result} =    Run Process    python    -m    cleveragents    context    delete
+    ...    ${context_name}
+    ...    --context-dir    ${CONTEXT_DIR}
+    ...    stdin=y\n
+
+    Should Be Equal As Integers    ${result.rc}    0
+    Directory Should Not Exist    ${CONTEXT_DIR}/${context_name}
+
+Test Delete Single Context With Confirmation Reject
+    [Documentation]    Test context delete with confirmation rejected
+    ${context_name} =    Set Variable    delete_reject_${UNIQUE_ID}
+
+    # Create context
+    Run Process    python    -m    cleveragents    run
+    ...    -c    ${SIMPLE_CONFIG}
+    ...    --context    ${context_name}
+    ...    --context-dir    ${CONTEXT_DIR}
+    ...    --unsafe
+    ...    -p    "test message"
+
+    Directory Should Exist    ${CONTEXT_DIR}/${context_name}
+
+    # Delete with confirmation rejected (answer 'n')
+    ${result} =    Run Process    python    -m    cleveragents    context    delete
+    ...    ${context_name}
+    ...    --context-dir    ${CONTEXT_DIR}
+    ...    stdin=n\n
+
+    Should Be Equal As Integers    ${result.rc}    0
+    Directory Should Exist    ${CONTEXT_DIR}/${context_name}
+    Should Contain    ${result.stdout}    cancelled
+
+Test Delete All Contexts With All And Yes Flags
+    [Documentation]    Test delete all contexts with --all --yes
+    [Setup]    Empty Directory    ${CONTEXT_DIR}
+    ${ctx1} =    Set Variable    all_ctx1_${UNIQUE_ID}
+    ${ctx2} =    Set Variable    all_ctx2_${UNIQUE_ID}
+    ${ctx3} =    Set Variable    all_ctx3_${UNIQUE_ID}
+
+    # Create multiple contexts
+    Run Process    python    -m    cleveragents    run
+    ...    -c    ${SIMPLE_CONFIG}
+    ...    --context    ${ctx1}
+    ...    --context-dir    ${CONTEXT_DIR}
+    ...    --unsafe
+    ...    -p    "test"
+
+    Run Process    python    -m    cleveragents    run
+    ...    -c    ${SIMPLE_CONFIG}
+    ...    --context    ${ctx2}
+    ...    --context-dir    ${CONTEXT_DIR}
+    ...    --unsafe
+    ...    -p    "test"
+
+    Run Process    python    -m    cleveragents    run
+    ...    -c    ${SIMPLE_CONFIG}
+    ...    --context    ${ctx3}
+    ...    --context-dir    ${CONTEXT_DIR}
+    ...    --unsafe
+    ...    -p    "test"
+
+    Directory Should Exist    ${CONTEXT_DIR}/${ctx1}
+    Directory Should Exist    ${CONTEXT_DIR}/${ctx2}
+    Directory Should Exist    ${CONTEXT_DIR}/${ctx3}
+
+    # Delete all with --all --yes
+    ${result} =    Run Process    python    -m    cleveragents    context    delete
+    ...    --all
+    ...    --yes
+    ...    --context-dir    ${CONTEXT_DIR}
+
+    Should Be Equal As Integers    ${result.rc}    0
+    Directory Should Not Exist    ${CONTEXT_DIR}/${ctx1}
+    Directory Should Not Exist    ${CONTEXT_DIR}/${ctx2}
+    Directory Should Not Exist    ${CONTEXT_DIR}/${ctx3}
+    Should Contain    ${result.stdout}    Deleted 3 context
+
+Test Delete All With Confirmation Accept
+    [Documentation]    Test delete all with confirmation accepted
+    [Setup]    Empty Directory    ${CONTEXT_DIR}
+    ${ctx1} =    Set Variable    all_confirm1_${UNIQUE_ID}
+    ${ctx2} =    Set Variable    all_confirm2_${UNIQUE_ID}
+
+    # Create contexts
+    Run Process    python    -m    cleveragents    run
+    ...    -c    ${SIMPLE_CONFIG}
+    ...    --context    ${ctx1}
+    ...    --context-dir    ${CONTEXT_DIR}
+    ...    --unsafe
+    ...    -p    "test"
+
+    Run Process    python    -m    cleveragents    run
+    ...    -c    ${SIMPLE_CONFIG}
+    ...    --context    ${ctx2}
+    ...    --context-dir    ${CONTEXT_DIR}
+    ...    --unsafe
+    ...    -p    "test"
+
+    # Delete all with confirmation
+    ${result} =    Run Process    python    -m    cleveragents    context    delete
+    ...    --all
+    ...    --context-dir    ${CONTEXT_DIR}
+    ...    stdin=y\n
+
+    Should Be Equal As Integers    ${result.rc}    0
+    Directory Should Not Exist    ${CONTEXT_DIR}/${ctx1}
+    Directory Should Not Exist    ${CONTEXT_DIR}/${ctx2}
+    Should Contain    ${result.stdout}    Found
+    Should Contain    ${result.stdout}    to delete
+
+Test Delete All With Confirmation Reject
+    [Documentation]    Test delete all with confirmation rejected
+    [Setup]    Empty Directory    ${CONTEXT_DIR}
+    ${ctx1} =    Set Variable    all_reject1_${UNIQUE_ID}
+    ${ctx2} =    Set Variable    all_reject2_${UNIQUE_ID}
+
+    # Create contexts
+    Run Process    python    -m    cleveragents    run
+    ...    -c    ${SIMPLE_CONFIG}
+    ...    --context    ${ctx1}
+    ...    --context-dir    ${CONTEXT_DIR}
+    ...    --unsafe
+    ...    -p    "test"
+
+    Run Process    python    -m    cleveragents    run
+    ...    -c    ${SIMPLE_CONFIG}
+    ...    --context    ${ctx2}
+    ...    --context-dir    ${CONTEXT_DIR}
+    ...    --unsafe
+    ...    -p    "test"
+
+    # Delete all with confirmation rejected
+    ${result} =    Run Process    python    -m    cleveragents    context    delete
+    ...    --all
+    ...    --context-dir    ${CONTEXT_DIR}
+    ...    stdin=n\n
+
+    Should Be Equal As Integers    ${result.rc}    0
+    Directory Should Exist    ${CONTEXT_DIR}/${ctx1}
+    Directory Should Exist    ${CONTEXT_DIR}/${ctx2}
+    Should Contain    ${result.stdout}    cancelled
+
+Test Error When Both Name And All Provided
+    [Documentation]    Test error when both NAME and --all are provided
+    ${result} =    Run Process    python    -m    cleveragents    context    delete
+    ...    test_context
+    ...    --all
+    ...    --context-dir    ${CONTEXT_DIR}
+
+    Should Not Be Equal As Integers    ${result.rc}    0
+    Should Contain Any    ${result.stderr}    ${result.stdout}    Cannot specify NAME when using --all
+
+Test Error When Neither Name Nor All Provided
+    [Documentation]    Test error when neither NAME nor --all is provided
+    ${result} =    Run Process    python    -m    cleveragents    context    delete
+    ...    --context-dir    ${CONTEXT_DIR}
+
+    Should Not Be Equal As Integers    ${result.rc}    0
+    Should Contain Any    ${result.stderr}    ${result.stdout}    Must specify NAME or use --all
+
+Test Delete All When No Contexts Exist
+    [Documentation]    Test delete all when directory is empty
+    # Ensure directory is empty
+    Empty Directory    ${CONTEXT_DIR}
+
+    ${result} =    Run Process    python    -m    cleveragents    context    delete
+    ...    --all
+    ...    --yes
+    ...    --context-dir    ${CONTEXT_DIR}
+
+    Should Be Equal As Integers    ${result.rc}    0
+    Should Contain    ${result.stdout}    No contexts found
+
+Test Delete Non Existent Context
+    [Documentation]    Test deleting a context that doesn't exist
+    ${result} =    Run Process    python    -m    cleveragents    context    delete
+    ...    non_existent_context_${UNIQUE_ID}
+    ...    --yes
+    ...    --context-dir    ${CONTEXT_DIR}
+
+    Should Not Be Equal As Integers    ${result.rc}    0
+    Should Contain Any    ${result.stderr}    ${result.stdout}    does not exist
+
+Test Delete All Shows Context List Before Deletion
+    [Documentation]    Test that --all shows context list before confirmation
+    [Setup]    Empty Directory    ${CONTEXT_DIR}
+    ${ctx1} =    Set Variable    list_ctx1_${UNIQUE_ID}
+    ${ctx2} =    Set Variable    list_ctx2_${UNIQUE_ID}
+    ${ctx3} =    Set Variable    list_ctx3_${UNIQUE_ID}
+
+    # Create contexts
+    Run Process    python    -m    cleveragents    run
+    ...    -c    ${SIMPLE_CONFIG}
+    ...    --context    ${ctx1}
+    ...    --context-dir    ${CONTEXT_DIR}
+    ...    --unsafe
+    ...    -p    "test"
+
+    Run Process    python    -m    cleveragents    run
+    ...    -c    ${SIMPLE_CONFIG}
+    ...    --context    ${ctx2}
+    ...    --context-dir    ${CONTEXT_DIR}
+    ...    --unsafe
+    ...    -p    "test"
+
+    Run Process    python    -m    cleveragents    run
+    ...    -c    ${SIMPLE_CONFIG}
+    ...    --context    ${ctx3}
+    ...    --context-dir    ${CONTEXT_DIR}
+    ...    --unsafe
+    ...    -p    "test"
+
+    # Delete all with confirmation to see list
+    ${result} =    Run Process    python    -m    cleveragents    context    delete
+    ...    --all
+    ...    --context-dir    ${CONTEXT_DIR}
+    ...    stdin=n\n
+
+    Should Contain    ${result.stdout}    Found 3 context
+    Should Contain    ${result.stdout}    ${ctx1}
+    Should Contain    ${result.stdout}    ${ctx2}
+    Should Contain    ${result.stdout}    ${ctx3}
+
+*** Keywords ***
+Setup Test Environment
+    ${timestamp} =    Get Current Date    result_format=%Y%m%d_%H%M%S
+    ${random} =    Evaluate    random.randint(1000, 9999)    modules=random
+    Set Suite Variable    ${UNIQUE_ID}    ${timestamp}_${random}
+    Set Suite Variable    ${TEMP}    ${TEMPDIR}/ca_delete_test_${UNIQUE_ID}
+    Set Suite Variable    ${CONTEXT_DIR}    ${TEMP}/contexts
+    Create Directory    ${TEMP}
+    Create Directory    ${CONTEXT_DIR}
+
+Cleanup Test Environment
+    Run Keyword And Ignore Error    Remove Directory    ${TEMP}    recursive=True
+
+Should Contain Any
+    [Arguments]    ${text1}    ${text2}    ${expected}
+    ${combined} =    Set Variable    ${text1}${text2}
+    Should Contain    ${combined}    ${expected}