fix: use per-chat plan file paths (#24268)

> This PR was authored by Mux on behalf of Mike. Chats sharing one workspace (e.g. sibling subagents) all wrote to `/home/coder/PLAN.md`, causing plan file collisions. This change derives a unique plan path per chat from the workspace home directory and chat ID. ## Changes * `write_file`, `edit_files`, and `propose_plan` reject any `plan.md` variant (case-insensitive) at the workspace home root, with a clear error pointing to the chat-specific path. * Root chats receive a `<plan-file-path>` block inlined in the main system prompt with the concrete path. * Prompt and tool descriptions no longer hardcode `/home/coder/PLAN.md`. * Plan path handling is POSIX-only (forward-slash), relying on the contract that workspace agent paths are normalized before reaching chatd. * Updated `ProposePlanTool.stories.tsx` to use per-chat path examples. * Full test coverage for plan path detection, legacy-path rejection in all three tools, inline prompt rendering, and fallback behavior.
2026-09-24 15:04:27 +08:00 · 2026-04-14 10:50:40 +02:00
parent 116323d3cf
commit a554de372a
15 changed files with 1708 additions and 33 deletions
@@ -2,6 +2,7 @@ package chattool

 import (
 	"context"
+	"strings"

 	"charm.land/fantasy"

@@ -10,6 +11,7 @@ import (

 type EditFilesOptions struct {
 	GetWorkspaceConn func(context.Context) (workspacesdk.AgentConn, error)
+	ResolvePlanPath  func(context.Context) (chatPath string, home string, err error)
 }

 type EditFilesArgs struct {
@@ -29,7 +31,7 @@ func EditFiles(options EditFilesOptions) fantasy.AgentTool {
 			if err != nil {
 				return fantasy.NewTextErrorResponse(err.Error()), nil
 			}
-			return executeEditFilesTool(ctx, conn, args)
+			return executeEditFilesTool(ctx, conn, args, options.ResolvePlanPath)
 		},
 	)
 }
@@ -38,11 +40,42 @@ func executeEditFilesTool(
 	ctx context.Context,
 	conn workspacesdk.AgentConn,
 	args EditFilesArgs,
+	resolvePlanPath func(context.Context) (chatPath string, home string, err error),
 ) (fantasy.ToolResponse, error) {
 	if len(args.Files) == 0 {
 		return fantasy.NewTextErrorResponse("files is required"), nil
 	}

+	var (
+		chatPath       string
+		home           string
+		planPathErr    error
+		planPathLoaded bool
+	)
+	for i := range args.Files {
+		args.Files[i].Path = strings.TrimSpace(args.Files[i].Path)
+		file := args.Files[i]
+
+		hasPlanFileName := looksLikePlanFileName(file.Path)
+		if hasPlanFileName && !isAbsolutePath(file.Path) {
+			return fantasy.NewTextErrorResponse(
+				"plan files must use absolute paths; use the chat-specific absolute plan path; no files in this batch were applied",
+			), nil
+		}
+		if resolvePlanPath == nil || !hasPlanFileName {
+			continue
+		}
+		if !planPathLoaded {
+			chatPath, home, planPathErr = resolvePlanPath(ctx)
+			planPathLoaded = true
+		}
+		if resp, rejected := rejectSharedPlanPath(file.Path, home, chatPath, planPathErr); rejected {
+			return fantasy.NewTextErrorResponse(
+				resp.Content + "; no files in this batch were applied",
+			), nil
+		}
+	}
+
 	if err := conn.EditFiles(ctx, workspacesdk.FileEditRequest{Files: args.Files}); err != nil {
 		return fantasy.NewTextErrorResponse(err.Error()), nil
 	}
@@ -0,0 +1,290 @@
+package chattool_test
+
+import (
+	"context"
+	"testing"
+
+	"charm.land/fantasy"
+	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/require"
+	"go.uber.org/mock/gomock"
+	"golang.org/x/xerrors"
+
+	"github.com/coder/coder/v2/coderd/x/chatd/chattool"
+	"github.com/coder/coder/v2/codersdk/workspacesdk"
+	"github.com/coder/coder/v2/codersdk/workspacesdk/agentconnmock"
+)
+
+func TestEditFiles(t *testing.T) {
+	t.Parallel()
+
+	t.Run("RejectsPlanPathsWhenResolvePlanPathIsConfigured", func(t *testing.T) {
+		t.Parallel()
+
+		tests := []struct {
+			name                 string
+			input                string
+			expectedRejectedPath string
+		}{
+			{
+				name:                 "SingleHomeRootPlanPath",
+				input:                `{"files":[{"path":"/Users/dev/plan.md","edits":[{"search":"old","replace":"new"}]}]}`,
+				expectedRejectedPath: "/Users/dev/plan.md",
+			},
+			{
+				name: "MultiFileBatchWithHomeRootPlanPath",
+				input: `{"files":[` +
+					`{"path":"/Users/dev/subdir/plan.md","edits":[{"search":"old","replace":"new"}]},` +
+					`{"path":"/Users/dev/plan.md","edits":[{"search":"old","replace":"new"}]}` +
+					`]}`,
+				expectedRejectedPath: "/Users/dev/plan.md",
+			},
+		}
+
+		for _, testCase := range tests {
+			t.Run(testCase.name, func(t *testing.T) {
+				t.Parallel()
+				ctrl := gomock.NewController(t)
+				mockConn := agentconnmock.NewMockAgentConn(ctrl)
+				resolvePlanPathCalls := 0
+				tool := chattool.EditFiles(chattool.EditFilesOptions{
+					GetWorkspaceConn: func(context.Context) (workspacesdk.AgentConn, error) {
+						return mockConn, nil
+					},
+					ResolvePlanPath: func(context.Context) (string, string, error) {
+						resolvePlanPathCalls++
+						return "/Users/dev/.coder/plans/PLAN-chat.md", "/Users/dev", nil
+					},
+				})
+
+				resp, err := tool.Run(context.Background(), fantasy.ToolCall{
+					ID:    "call-1",
+					Name:  "edit_files",
+					Input: testCase.input,
+				})
+				require.NoError(t, err)
+				assert.True(t, resp.IsError)
+				assert.Equal(t, 1, resolvePlanPathCalls)
+				assert.Equal(
+					t,
+					editFilesBatchRejectedMessage(sharedPlanPathResolvedMessage(
+						testCase.expectedRejectedPath,
+						"/Users/dev/.coder/plans/PLAN-chat.md",
+					)),
+					resp.Content,
+				)
+			})
+		}
+	})
+
+	t.Run("RejectsSharedPlanPathWhenResolverFails", func(t *testing.T) {
+		t.Parallel()
+		ctrl := gomock.NewController(t)
+		mockConn := agentconnmock.NewMockAgentConn(ctrl)
+		tool := chattool.EditFiles(chattool.EditFilesOptions{
+			GetWorkspaceConn: func(context.Context) (workspacesdk.AgentConn, error) {
+				return mockConn, nil
+			},
+			ResolvePlanPath: func(context.Context) (string, string, error) {
+				return "", "", xerrors.New("workspace unavailable")
+			},
+		})
+
+		resp, err := tool.Run(context.Background(), fantasy.ToolCall{
+			ID:    "call-1",
+			Name:  "edit_files",
+			Input: `{"files":[{"path":"/home/coder/plan.md","edits":[{"search":"old","replace":"new"}]}]}`,
+		})
+		require.NoError(t, err)
+		assert.True(t, resp.IsError)
+		assert.Equal(t, editFilesBatchRejectedMessage(planPathVerificationMessage("/home/coder/plan.md")), resp.Content)
+	})
+
+	t.Run("RejectsRelativePlanPathsWhenResolvePlanPathIsConfigured", func(t *testing.T) {
+		t.Parallel()
+		ctrl := gomock.NewController(t)
+		mockConn := agentconnmock.NewMockAgentConn(ctrl)
+		resolvePlanPathCalled := false
+		tool := chattool.EditFiles(chattool.EditFilesOptions{
+			GetWorkspaceConn: func(context.Context) (workspacesdk.AgentConn, error) {
+				return mockConn, nil
+			},
+			ResolvePlanPath: func(context.Context) (string, string, error) {
+				resolvePlanPathCalled = true
+				return "/home/coder/.coder/plans/PLAN-chat.md", "/home/coder", nil
+			},
+		})
+
+		resp, err := tool.Run(context.Background(), fantasy.ToolCall{
+			ID:    "call-1",
+			Name:  "edit_files",
+			Input: `{"files":[{"path":"plan.md","edits":[{"search":"old","replace":"new"}]}]}`,
+		})
+		require.NoError(t, err)
+		assert.True(t, resp.IsError)
+		assert.False(t, resolvePlanPathCalled)
+		assert.Equal(t, editFilesBatchRejectedMessage(relativePlanPathMessage()), resp.Content)
+	})
+
+	t.Run("PerChatPlanPathIsAllowed", func(t *testing.T) {
+		t.Parallel()
+		ctrl := gomock.NewController(t)
+		mockConn := agentconnmock.NewMockAgentConn(ctrl)
+		chatPlanPath := "/home/coder/.coder/plans/PLAN-123e4567-e89b-12d3-a456-426614174000.md"
+		request := workspacesdk.FileEditRequest{Files: []workspacesdk.FileEdits{{
+			Path: chatPlanPath,
+			Edits: []workspacesdk.FileEdit{{
+				Search:  "old",
+				Replace: "new",
+			}},
+		}}}
+		mockConn.EXPECT().EditFiles(gomock.Any(), request).Return(nil)
+
+		resolvePlanPathCalled := false
+		tool := chattool.EditFiles(chattool.EditFilesOptions{
+			GetWorkspaceConn: func(context.Context) (workspacesdk.AgentConn, error) {
+				return mockConn, nil
+			},
+			ResolvePlanPath: func(context.Context) (string, string, error) {
+				resolvePlanPathCalled = true
+				return chatPlanPath, "/home/coder", nil
+			},
+		})
+
+		resp, err := tool.Run(context.Background(), fantasy.ToolCall{
+			ID:    "call-1",
+			Name:  "edit_files",
+			Input: `{"files":[{"path":"` + chatPlanPath + `","edits":[{"search":"old","replace":"new"}]}]}`,
+		})
+		require.NoError(t, err)
+		assert.False(t, resp.IsError)
+		assert.False(t, resolvePlanPathCalled)
+	})
+
+	t.Run("NestedPlanPathAllowedWhenResolverFails", func(t *testing.T) {
+		t.Parallel()
+		ctrl := gomock.NewController(t)
+		mockConn := agentconnmock.NewMockAgentConn(ctrl)
+		request := workspacesdk.FileEditRequest{Files: []workspacesdk.FileEdits{{
+			Path: "/home/coder/myproject/plan.md",
+			Edits: []workspacesdk.FileEdit{{
+				Search:  "old",
+				Replace: "new",
+			}},
+		}}}
+		mockConn.EXPECT().EditFiles(gomock.Any(), request).Return(nil)
+
+		tool := chattool.EditFiles(chattool.EditFilesOptions{
+			GetWorkspaceConn: func(context.Context) (workspacesdk.AgentConn, error) {
+				return mockConn, nil
+			},
+			ResolvePlanPath: func(context.Context) (string, string, error) {
+				return "", "", xerrors.New("workspace unavailable")
+			},
+		})
+
+		resp, err := tool.Run(context.Background(), fantasy.ToolCall{
+			ID:    "call-1",
+			Name:  "edit_files",
+			Input: `{"files":[{"path":"/home/coder/myproject/plan.md","edits":[{"search":"old","replace":"new"}]}]}`,
+		})
+		require.NoError(t, err)
+		assert.False(t, resp.IsError)
+	})
+
+	t.Run("NestedPlanPathUnderHomeIsAllowed", func(t *testing.T) {
+		t.Parallel()
+		ctrl := gomock.NewController(t)
+		mockConn := agentconnmock.NewMockAgentConn(ctrl)
+		request := workspacesdk.FileEditRequest{Files: []workspacesdk.FileEdits{{
+			Path: "/home/coder/myproject/plan.md",
+			Edits: []workspacesdk.FileEdit{{
+				Search:  "old",
+				Replace: "new",
+			}},
+		}}}
+		mockConn.EXPECT().EditFiles(gomock.Any(), request).Return(nil)
+
+		planPathCalled := false
+		tool := chattool.EditFiles(chattool.EditFilesOptions{
+			GetWorkspaceConn: func(context.Context) (workspacesdk.AgentConn, error) {
+				return mockConn, nil
+			},
+			ResolvePlanPath: func(context.Context) (string, string, error) {
+				planPathCalled = true
+				return "/home/coder/.coder/plans/PLAN-chat.md", "/home/coder", nil
+			},
+		})
+
+		resp, err := tool.Run(context.Background(), fantasy.ToolCall{
+			ID:    "call-1",
+			Name:  "edit_files",
+			Input: `{"files":[{"path":"/home/coder/myproject/plan.md","edits":[{"search":"old","replace":"new"}]}]}`,
+		})
+		require.NoError(t, err)
+		assert.False(t, resp.IsError)
+		assert.True(t, planPathCalled)
+	})
+
+	t.Run("AllowsNonSharedPath", func(t *testing.T) {
+		t.Parallel()
+		ctrl := gomock.NewController(t)
+		mockConn := agentconnmock.NewMockAgentConn(ctrl)
+		request := workspacesdk.FileEditRequest{Files: []workspacesdk.FileEdits{{
+			Path: "/home/dev/my-plan.md",
+			Edits: []workspacesdk.FileEdit{{
+				Search:  "old",
+				Replace: "new",
+			}},
+		}}}
+		mockConn.EXPECT().EditFiles(gomock.Any(), request).Return(nil)
+
+		resolvePlanPathCalled := false
+		tool := chattool.EditFiles(chattool.EditFilesOptions{
+			GetWorkspaceConn: func(context.Context) (workspacesdk.AgentConn, error) {
+				return mockConn, nil
+			},
+			ResolvePlanPath: func(context.Context) (string, string, error) {
+				resolvePlanPathCalled = true
+				return "", "", xerrors.New("should not be called")
+			},
+		})
+
+		resp, err := tool.Run(context.Background(), fantasy.ToolCall{
+			ID:    "call-1",
+			Name:  "edit_files",
+			Input: `{"files":[{"path":"/home/dev/my-plan.md","edits":[{"search":"old","replace":"new"}]}]}`,
+		})
+		require.NoError(t, err)
+		assert.False(t, resp.IsError)
+		assert.False(t, resolvePlanPathCalled)
+	})
+
+	t.Run("AllowsSharedPlanPathWhenResolvePlanPathIsNil", func(t *testing.T) {
+		t.Parallel()
+		ctrl := gomock.NewController(t)
+		mockConn := agentconnmock.NewMockAgentConn(ctrl)
+		request := workspacesdk.FileEditRequest{Files: []workspacesdk.FileEdits{{
+			Path: chattool.LegacySharedPlanPath,
+			Edits: []workspacesdk.FileEdit{{
+				Search:  "old",
+				Replace: "new",
+			}},
+		}}}
+		mockConn.EXPECT().EditFiles(gomock.Any(), request).Return(nil)
+
+		tool := chattool.EditFiles(chattool.EditFilesOptions{
+			GetWorkspaceConn: func(context.Context) (workspacesdk.AgentConn, error) {
+				return mockConn, nil
+			},
+		})
+
+		resp, err := tool.Run(context.Background(), fantasy.ToolCall{
+			ID:    "call-1",
+			Name:  "edit_files",
+			Input: `{"files":[{"path":"` + chattool.LegacySharedPlanPath + `","edits":[{"search":"old","replace":"new"}]}]}`,
+		})
+		require.NoError(t, err)
+		assert.False(t, resp.IsError)
+	})
+}
@@ -0,0 +1,90 @@
+package chattool
+
+import (
+	"context"
+	"path"
+	"strings"
+
+	"github.com/google/uuid"
+	"golang.org/x/xerrors"
+
+	"github.com/coder/coder/v2/codersdk/workspacesdk"
+)
+
+const planFileNamePrefix = "PLAN-"
+
+// LegacySharedPlanPath is the original shared plan file path used by
+// every chat in a workspace.
+const LegacySharedPlanPath = "/home/coder/PLAN.md"
+
+// ResolveWorkspaceHome returns the workspace user's home directory.
+func ResolveWorkspaceHome(
+	ctx context.Context,
+	conn workspacesdk.AgentConn,
+) (string, error) {
+	if conn == nil {
+		return "", xerrors.New("workspace connection is required")
+	}
+
+	resp, err := conn.LS(ctx, "", workspacesdk.LSRequest{
+		Path:       []string{},
+		Relativity: workspacesdk.LSRelativityHome,
+	})
+	if err != nil {
+		return "", xerrors.Errorf("resolve workspace home: %w", err)
+	}
+
+	home := strings.TrimSpace(resp.AbsolutePathString)
+	if home == "" {
+		return "", xerrors.New("workspace home path is empty")
+	}
+
+	return home, nil
+}
+
+// PlanPathForChat returns the per-chat plan file path rooted in the
+// workspace home directory.
+func PlanPathForChat(home string, chatID uuid.UUID) string {
+	return path.Join(
+		home,
+		".coder",
+		"plans",
+		planFileNamePrefix+chatID.String()+".md",
+	)
+}
+
+// chatd consumes agent-normalized POSIX paths. Workspace agents are
+// expected to convert separators to forward slashes before these
+// helpers run.
+
+// isAbsolutePath reports whether p is an absolute POSIX path.
+func isAbsolutePath(p string) bool {
+	return path.IsAbs(p)
+}
+
+// looksLikePlanFileName reports whether the base name of requestedPath
+// is "plan.md" (case-insensitive), ignoring the directory component.
+func looksLikePlanFileName(requestedPath string) bool {
+	cleaned := path.Clean(requestedPath)
+	return strings.EqualFold(path.Base(cleaned), "plan.md")
+}
+
+// LooksLikeHomePlanFile reports whether requestedPath is a plan.md
+// variant (case-insensitive) sitting directly in the workspace home
+// directory.
+// The filename is compared case-insensitively because LLM output varies.
+func LooksLikeHomePlanFile(requestedPath, home string) bool {
+	normalized := path.Clean(requestedPath)
+	normalizedHome := path.Clean(home)
+
+	return looksLikePlanFileName(normalized) &&
+		strings.EqualFold(path.Dir(normalized), normalizedHome)
+}
+
+// looksLikeLegacySharedPlanPath reports whether requestedPath
+// matches the legacy shared plan path (case-insensitive). Used as a
+// narrow fallback when the workspace home cannot be resolved.
+func looksLikeLegacySharedPlanPath(requestedPath string) bool {
+	normalized := path.Clean(requestedPath)
+	return strings.EqualFold(normalized, LegacySharedPlanPath)
+}
@@ -0,0 +1,132 @@
+package chattool
+
+import (
+	"testing"
+
+	"github.com/stretchr/testify/require"
+)
+
+func TestIsAbsolutePath(t *testing.T) {
+	t.Parallel()
+
+	tests := []struct {
+		path string
+		want bool
+	}{
+		{"/home/coder/PLAN.md", true},
+		{"/workspace/project/plan.md", true},
+		{"plan.md", false},
+		{"./plan.md", false},
+		{"../plan.md", false},
+		{"", false},
+	}
+
+	for _, tt := range tests {
+		t.Run(tt.path, func(t *testing.T) {
+			t.Parallel()
+			require.Equal(t, tt.want, isAbsolutePath(tt.path))
+		})
+	}
+}
+
+func TestLooksLikePlanFileName(t *testing.T) {
+	t.Parallel()
+
+	require.True(t, looksLikePlanFileName("plan.md"))
+	require.True(t, looksLikePlanFileName("./Plan.md"))
+	require.True(t, looksLikePlanFileName("/home/coder/PLAN.md"))
+	require.False(t, looksLikePlanFileName("/home/coder/README.md"))
+}
+
+func TestLooksLikeLegacySharedPlanPath(t *testing.T) {
+	t.Parallel()
+
+	tests := []struct {
+		name      string
+		requested string
+		want      bool
+	}{
+		{
+			name:      "ExactMatch",
+			requested: "/home/coder/PLAN.md",
+			want:      true,
+		},
+		{
+			name:      "CaseInsensitive",
+			requested: "/home/coder/plan.md",
+			want:      true,
+		},
+		{
+			name:      "MixedCase",
+			requested: "/home/coder/Plan.md",
+			want:      true,
+		},
+		{
+			name:      "NestedPath",
+			requested: "/home/coder/myproject/plan.md",
+			want:      false,
+		},
+		{
+			name:      "DifferentHome",
+			requested: "/Users/dev/PLAN.md",
+			want:      false,
+		},
+		{
+			name:      "PerChatPath",
+			requested: "/home/coder/.coder/plans/PLAN-123e4567-e89b-12d3-a456-426614174000.md",
+			want:      false,
+		},
+		{
+			name:      "EmptyString",
+			requested: "",
+			want:      false,
+		},
+	}
+
+	for _, testCase := range tests {
+		t.Run(testCase.name, func(t *testing.T) {
+			t.Parallel()
+			require.Equal(t, testCase.want, looksLikeLegacySharedPlanPath(testCase.requested))
+		})
+	}
+}
+
+func TestRejectSharedPlanPath(t *testing.T) {
+	t.Parallel()
+
+	resp, rejected := rejectSharedPlanPath(
+		LegacySharedPlanPath,
+		"/Users/dev",
+		"/Users/dev/.coder/plans/PLAN-chat.md",
+		nil,
+	)
+
+	require.True(t, rejected)
+	require.True(t, resp.IsError)
+	require.Equal(
+		t,
+		sharedPlanPathMessage(
+			LegacySharedPlanPath,
+			"/Users/dev/.coder/plans/PLAN-chat.md",
+		),
+		resp.Content,
+	)
+}
+
+func TestSharedPlanPathMessage(t *testing.T) {
+	t.Parallel()
+
+	require.Equal(
+		t,
+		"the plan path /home/coder/plan.md is no longer supported at the home root; use the chat-specific plan path: /home/coder/.coder/plans/PLAN-chat.md",
+		sharedPlanPathMessage(
+			"/home/coder/plan.md",
+			"/home/coder/.coder/plans/PLAN-chat.md",
+		),
+	)
+	require.Equal(
+		t,
+		"the plan path /home/coder/plan.md could not be verified because the workspace is currently unavailable to resolve the chat-specific plan path, try again shortly",
+		planPathVerificationMessage("/home/coder/plan.md"),
+	)
+}
@@ -0,0 +1,219 @@
+package chattool_test
+
+import (
+	"context"
+	"strings"
+	"testing"
+
+	"github.com/google/uuid"
+	"github.com/stretchr/testify/require"
+	"go.uber.org/mock/gomock"
+	"golang.org/x/xerrors"
+
+	"github.com/coder/coder/v2/coderd/x/chatd/chattool"
+	"github.com/coder/coder/v2/codersdk/workspacesdk"
+	"github.com/coder/coder/v2/codersdk/workspacesdk/agentconnmock"
+)
+
+func TestResolveWorkspaceHome(t *testing.T) {
+	t.Parallel()
+
+	tests := []struct {
+		name     string
+		resp     workspacesdk.LSResponse
+		lsErr    error
+		want     string
+		wantErr  bool
+		errMatch string
+	}{
+		{
+			name: "StandardLinuxHome",
+			resp: workspacesdk.LSResponse{AbsolutePathString: "/home/coder"},
+			want: "/home/coder",
+		},
+		{
+			name: "NonStandardHome",
+			resp: workspacesdk.LSResponse{AbsolutePathString: "/Users/dev"},
+			want: "/Users/dev",
+		},
+		{
+			name:     "LSError",
+			lsErr:    xerrors.New("list failed"),
+			wantErr:  true,
+			errMatch: "list failed",
+		},
+		{
+			name:     "EmptyAbsolutePathString",
+			resp:     workspacesdk.LSResponse{AbsolutePathString: ""},
+			wantErr:  true,
+			errMatch: "workspace home path is empty",
+		},
+		{
+			name:     "WhitespaceOnlyAbsolutePathString",
+			resp:     workspacesdk.LSResponse{AbsolutePathString: " \t\n "},
+			wantErr:  true,
+			errMatch: "workspace home path is empty",
+		},
+	}
+
+	for _, testCase := range tests {
+		t.Run(testCase.name, func(t *testing.T) {
+			t.Parallel()
+
+			ctrl := gomock.NewController(t)
+			conn := agentconnmock.NewMockAgentConn(ctrl)
+
+			conn.EXPECT().LS(
+				gomock.Any(),
+				"",
+				workspacesdk.LSRequest{
+					Path:       []string{},
+					Relativity: workspacesdk.LSRelativityHome,
+				},
+			).Return(testCase.resp, testCase.lsErr)
+
+			got, err := chattool.ResolveWorkspaceHome(context.Background(), conn)
+			if testCase.wantErr {
+				require.Error(t, err)
+				require.ErrorContains(t, err, testCase.errMatch)
+				require.Empty(t, got)
+				return
+			}
+
+			require.NoError(t, err)
+			require.Equal(t, testCase.want, got)
+		})
+	}
+}
+
+func TestPlanPathForChat(t *testing.T) {
+	t.Parallel()
+
+	t.Run("StandardHome", func(t *testing.T) {
+		t.Parallel()
+
+		chatID := uuid.MustParse("123e4567-e89b-12d3-a456-426614174000")
+
+		got := chattool.PlanPathForChat("/home/coder", chatID)
+
+		require.Equal(
+			t,
+			"/home/coder/.coder/plans/PLAN-123e4567-e89b-12d3-a456-426614174000.md",
+			got,
+		)
+	})
+
+	t.Run("NonStandardHome", func(t *testing.T) {
+		t.Parallel()
+
+		chatID := uuid.MustParse("aaaaaaaa-bbbb-cccc-dddd-eeeeeeeeeeee")
+
+		got := chattool.PlanPathForChat("/Users/dev", chatID)
+
+		require.Equal(
+			t,
+			"/Users/dev/.coder/plans/PLAN-aaaaaaaa-bbbb-cccc-dddd-eeeeeeeeeeee.md",
+			got,
+		)
+	})
+
+	t.Run("MatchesExpectedFormat", func(t *testing.T) {
+		t.Parallel()
+
+		home := "/workspace/home"
+		chatID := uuid.MustParse("f47ac10b-58cc-4372-a567-0e02b2c3d479")
+
+		got := chattool.PlanPathForChat(home, chatID)
+
+		require.True(t, strings.HasPrefix(got, home+"/.coder/plans/PLAN-"))
+		require.True(t, strings.HasSuffix(got, chatID.String()+".md"))
+	})
+}
+
+func TestLooksLikeHomePlanFile(t *testing.T) {
+	t.Parallel()
+
+	tests := []struct {
+		name      string
+		requested string
+		home      string
+		want      bool
+	}{
+		{
+			name:      "UppercaseHomeRootPlan",
+			requested: "/home/coder/PLAN.md",
+			home:      "/home/coder",
+			want:      true,
+		},
+		{
+			name:      "LowercaseHomeRootPlan",
+			requested: "/home/coder/plan.md",
+			home:      "/home/coder",
+			want:      true,
+		},
+		{
+			name:      "MixedCaseHomeRootPlan",
+			requested: "/home/coder/Plan.md",
+			home:      "/home/coder",
+			want:      true,
+		},
+		{
+			name:      "UppercaseExtension",
+			requested: "/home/coder/PLAN.MD",
+			home:      "/home/coder",
+			want:      true,
+		},
+		{
+			name:      "CustomHomeRootPlan",
+			requested: "/Users/dev/plan.md",
+			home:      "/Users/dev",
+			want:      true,
+		},
+		{
+			name:      "NestedPlanUnderHome",
+			requested: "/home/coder/myproject/plan.md",
+			home:      "/home/coder",
+			want:      false,
+		},
+		{
+			name:      "PerChatPlanPath",
+			requested: "/home/coder/.coder/plans/PLAN-123e4567-e89b-12d3-a456-426614174000.md",
+			home:      "/home/coder",
+			want:      false,
+		},
+		{
+			name:      "DifferentFilename",
+			requested: "/home/coder/README.md",
+			home:      "/home/coder",
+			want:      false,
+		},
+		{
+			name:      "DifferentExtension",
+			requested: "/home/coder/plan.txt",
+			home:      "/home/coder",
+			want:      false,
+		},
+		{
+			name:      "EmptyPath",
+			requested: "",
+			home:      "/home/coder",
+			want:      false,
+		},
+		{
+			name:      "DifferentHomeMismatch",
+			requested: "/home/coder/plan.md",
+			home:      "/Users/dev",
+			want:      false,
+		},
+	}
+
+	for _, testCase := range tests {
+		t.Run(testCase.name, func(t *testing.T) {
+			t.Parallel()
+
+			got := chattool.LooksLikeHomePlanFile(testCase.requested, testCase.home)
+
+			require.Equal(t, testCase.want, got)
+		})
+	}
+}
@@ -0,0 +1,54 @@
+package chattool
+
+import (
+	"fmt"
+
+	"charm.land/fantasy"
+)
+
+// rejectSharedPlanPath reports whether requestedPath targets the shared
+// home-root plan file and, if so, returns a rejection response that
+// points callers at the chat-specific plan path.
+func rejectSharedPlanPath(
+	requestedPath string,
+	home string,
+	chatPath string,
+	planPathErr error,
+) (fantasy.ToolResponse, bool) {
+	if planPathErr != nil {
+		// When the resolver fails, we cannot determine the actual
+		// home directory. Fall back to rejecting only the exact
+		// legacy shared path (case-insensitive) rather than every
+		// file named plan.md.
+		if !looksLikeLegacySharedPlanPath(requestedPath) {
+			return fantasy.ToolResponse{}, false
+		}
+
+		return fantasy.NewTextErrorResponse(
+			planPathVerificationMessage(requestedPath),
+		), true
+	}
+
+	if !LooksLikeHomePlanFile(requestedPath, home) && !looksLikeLegacySharedPlanPath(requestedPath) {
+		return fantasy.ToolResponse{}, false
+	}
+
+	return fantasy.NewTextErrorResponse(
+		sharedPlanPathMessage(requestedPath, chatPath),
+	), true
+}
+
+func sharedPlanPathMessage(requestedPath, chatPath string) string {
+	return fmt.Sprintf(
+		"the plan path %s is no longer supported at the home root; use the chat-specific plan path: %s",
+		requestedPath,
+		chatPath,
+	)
+}
+
+func planPathVerificationMessage(requestedPath string) string {
+	return fmt.Sprintf(
+		"the plan path %s could not be verified because the workspace is currently unavailable to resolve the chat-specific plan path, try again shortly",
+		requestedPath,
+	)
+}
@@ -17,6 +17,7 @@ const maxProposePlanSize = 32 * 1024 // 32 KiB
 // ProposePlanOptions configures the propose_plan tool.
 type ProposePlanOptions struct {
 	GetWorkspaceConn func(context.Context) (workspacesdk.AgentConn, error)
+	ResolvePlanPath  func(context.Context) (chatPath string, home string, err error)
 	StoreFile        func(ctx context.Context, name string, mediaType string, data []byte) (uuid.UUID, error)
 }

@@ -31,8 +32,9 @@ func ProposePlan(options ProposePlanOptions) fantasy.AgentTool {
 	return fantasy.NewAgentTool(
 		"propose_plan",
 		"Present a Markdown plan file from the workspace for user review. "+
-			"The file must already exist with a .md extension — use write_file to create it or edit_files to refine it before calling this tool. "+
-			"Pass the absolute file path (e.g. /home/coder/PLAN.md). The tool reads the content from the workspace.",
+			"The file must already exist with a .md extension. Use write_file to create it or edit_files to refine it before calling this tool. "+
+			"Pass the absolute file path to the plan. Important: use the chat-specific absolute plan path, not a generic path like PLAN.md in the home directory. "+
+			"The tool reads the content from the workspace.",
 		func(ctx context.Context, args ProposePlanArgs, _ fantasy.ToolCall) (fantasy.ToolResponse, error) {
 			if options.GetWorkspaceConn == nil {
 				return fantasy.NewTextErrorResponse("workspace connection resolver is not configured"), nil
@@ -44,7 +46,7 @@ func ProposePlan(options ProposePlanOptions) fantasy.AgentTool {
 			if err != nil {
 				return fantasy.NewTextErrorResponse(err.Error()), nil
 			}
-			return executeProposePlanTool(ctx, conn, args, options.StoreFile)
+			return executeProposePlanTool(ctx, conn, args, options.ResolvePlanPath, options.StoreFile)
 		},
 	)
 }
@@ -53,17 +55,32 @@ func executeProposePlanTool(
 	ctx context.Context,
 	conn workspacesdk.AgentConn,
 	args ProposePlanArgs,
+	resolvePlanPath func(context.Context) (chatPath string, home string, err error),
 	storeFile func(ctx context.Context, name string, mediaType string, data []byte) (uuid.UUID, error),
 ) (fantasy.ToolResponse, error) {
-	path := strings.TrimSpace(args.Path)
-	if path == "" {
-		return fantasy.NewTextErrorResponse("path is required (use an absolute path, e.g. /home/coder/PLAN.md)"), nil
+	requestedPath := strings.TrimSpace(args.Path)
+	if requestedPath == "" {
+		return fantasy.NewTextErrorResponse("path is required (use the chat-specific absolute plan path)"), nil
 	}
-	if !strings.HasSuffix(path, ".md") {
+	if !strings.HasSuffix(requestedPath, ".md") {
 		return fantasy.NewTextErrorResponse("path must end with .md"), nil
 	}

-	rc, _, err := conn.ReadFile(ctx, path, 0, maxProposePlanSize+1)
+	hasPlanFileName := looksLikePlanFileName(requestedPath)
+	if hasPlanFileName && !isAbsolutePath(requestedPath) {
+		return fantasy.NewTextErrorResponse(
+			"plan files must use absolute paths; use the chat-specific absolute plan path",
+		), nil
+	}
+
+	if resolvePlanPath != nil && hasPlanFileName {
+		chatPath, home, err := resolvePlanPath(ctx)
+		if resp, rejected := rejectSharedPlanPath(requestedPath, home, chatPath, err); rejected {
+			return resp, nil
+		}
+	}
+
+	rc, _, err := conn.ReadFile(ctx, requestedPath, 0, maxProposePlanSize+1)
 	if err != nil {
 		return fantasy.NewTextErrorResponse(err.Error()), nil
 	}
@@ -77,14 +94,14 @@ func executeProposePlanTool(
 		return fantasy.NewTextErrorResponse("plan file exceeds 32 KiB size limit"), nil
 	}

-	fileID, err := storeFile(ctx, filepath.Base(path), "text/markdown", data)
+	fileID, err := storeFile(ctx, filepath.Base(requestedPath), "text/markdown", data)
 	if err != nil {
 		return fantasy.NewTextErrorResponse("failed to store plan file: " + err.Error()), nil
 	}

 	return toolResponse(map[string]any{
 		"ok":         true,
-		"path":       path,
+		"path":       requestedPath,
 		"kind":       "plan",
 		"file_id":    fileID.String(),
 		"media_type": "text/markdown",
@@ -82,6 +82,34 @@ func TestProposePlan(t *testing.T) {
 		assert.Contains(t, resp.Content, "path must end with .md")
 	})

+	t.Run("RelativePlanPathReturnsError", func(t *testing.T) {
+		t.Parallel()
+		ctrl := gomock.NewController(t)
+		mockConn := agentconnmock.NewMockAgentConn(ctrl)
+
+		storeFile, _ := fakeStoreFile(t)
+		resolvePlanPathCalled := false
+		tool := newProposePlanToolWithPlanPath(
+			t,
+			mockConn,
+			storeFile,
+			func(context.Context) (string, string, error) {
+				resolvePlanPathCalled = true
+				return "/home/coder/.coder/plans/PLAN-chat.md", "/home/coder", nil
+			},
+		)
+
+		resp, err := tool.Run(context.Background(), fantasy.ToolCall{
+			ID:    "call-1",
+			Name:  "propose_plan",
+			Input: `{"path":"plan.md"}`,
+		})
+		require.NoError(t, err)
+		assert.True(t, resp.IsError)
+		assert.False(t, resolvePlanPathCalled)
+		assert.Equal(t, relativePlanPathMessage(), resp.Content)
+	})
+
 	t.Run("OversizedFileRejected", func(t *testing.T) {
 		t.Parallel()
 		ctrl := gomock.NewController(t)
@@ -135,7 +163,16 @@ func TestProposePlan(t *testing.T) {
 			Return(io.NopCloser(strings.NewReader("# Plan\n\nContent")), "text/markdown", nil)

 		storeFile, stored := fakeStoreFile(t)
-		tool := newProposePlanTool(t, mockConn, storeFile)
+		planPathCalled := false
+		tool := newProposePlanToolWithPlanPath(
+			t,
+			mockConn,
+			storeFile,
+			func(context.Context) (string, string, error) {
+				planPathCalled = true
+				return "/home/coder/.coder/plans/PLAN-xxx.md", "/home/coder", nil
+			},
+		)
 		resp, err := tool.Run(context.Background(), fantasy.ToolCall{
 			ID:    "call-1",
 			Name:  "propose_plan",
@@ -143,6 +180,7 @@ func TestProposePlan(t *testing.T) {
 		})
 		require.NoError(t, err)
 		assert.False(t, resp.IsError)
+		assert.True(t, planPathCalled)

 		result := decodeProposePlanResponse(t, resp)
 		assert.True(t, result.OK)
@@ -154,6 +192,41 @@ func TestProposePlan(t *testing.T) {
 		assert.NotContains(t, resp.Content, "content")
 	})

+	t.Run("NestedPlanPathUnderHomeIsAllowed", func(t *testing.T) {
+		t.Parallel()
+		ctrl := gomock.NewController(t)
+		mockConn := agentconnmock.NewMockAgentConn(ctrl)
+
+		mockConn.EXPECT().
+			ReadFile(gomock.Any(), "/home/coder/myproject/plan.md", int64(0), int64(32*1024+1)).
+			Return(io.NopCloser(strings.NewReader("# Nested Plan")), "text/markdown", nil)
+
+		storeFile, stored := fakeStoreFile(t)
+		planPathCalled := false
+		tool := newProposePlanToolWithPlanPath(
+			t,
+			mockConn,
+			storeFile,
+			func(context.Context) (string, string, error) {
+				planPathCalled = true
+				return "/home/coder/.coder/plans/PLAN-chat.md", "/home/coder", nil
+			},
+		)
+		resp, err := tool.Run(context.Background(), fantasy.ToolCall{
+			ID:    "call-1",
+			Name:  "propose_plan",
+			Input: `{"path":"/home/coder/myproject/plan.md"}`,
+		})
+		require.NoError(t, err)
+		assert.False(t, resp.IsError)
+		assert.True(t, planPathCalled)
+
+		result := decodeProposePlanResponse(t, resp)
+		assert.True(t, result.OK)
+		assert.Equal(t, "/home/coder/myproject/plan.md", result.Path)
+		assert.Equal(t, []byte("# Nested Plan"), *stored)
+	})
+
 	t.Run("FileNotFound", func(t *testing.T) {
 		t.Parallel()
 		ctrl := gomock.NewController(t)
@@ -218,6 +291,128 @@ func TestProposePlan(t *testing.T) {
 		assert.Contains(t, resp.Content, "storage unavailable")
 	})

+	t.Run("RejectsSharedPlanPathWithResolvedPath", func(t *testing.T) {
+		t.Parallel()
+		ctrl := gomock.NewController(t)
+		mockConn := agentconnmock.NewMockAgentConn(ctrl)
+
+		storeFile, _ := fakeStoreFile(t)
+		tool := newProposePlanToolWithPlanPath(
+			t,
+			mockConn,
+			storeFile,
+			func(context.Context) (string, string, error) {
+				return "/home/coder/.coder/plans/PLAN-chat.md", "/home/coder", nil
+			},
+		)
+
+		resp, err := tool.Run(context.Background(), fantasy.ToolCall{
+			ID:    "call-1",
+			Name:  "propose_plan",
+			Input: `{"path":"` + chattool.LegacySharedPlanPath + `"}`,
+		})
+		require.NoError(t, err)
+		assert.True(t, resp.IsError)
+		assert.Equal(
+			t,
+			sharedPlanPathResolvedMessage(chattool.LegacySharedPlanPath, "/home/coder/.coder/plans/PLAN-chat.md"),
+			resp.Content,
+		)
+	})
+
+	t.Run("RejectsSharedPlanPathWhenResolverFails", func(t *testing.T) {
+		t.Parallel()
+		ctrl := gomock.NewController(t)
+		mockConn := agentconnmock.NewMockAgentConn(ctrl)
+
+		storeFile, _ := fakeStoreFile(t)
+		tool := newProposePlanToolWithPlanPath(
+			t,
+			mockConn,
+			storeFile,
+			func(context.Context) (string, string, error) {
+				return "", "", xerrors.New("workspace unavailable")
+			},
+		)
+
+		resp, err := tool.Run(context.Background(), fantasy.ToolCall{
+			ID:    "call-1",
+			Name:  "propose_plan",
+			Input: `{"path":"` + chattool.LegacySharedPlanPath + `"}`,
+		})
+		require.NoError(t, err)
+		assert.True(t, resp.IsError)
+		assert.Equal(t, planPathVerificationMessage(chattool.LegacySharedPlanPath), resp.Content)
+	})
+
+	t.Run("PerChatPlanPathIsAllowed", func(t *testing.T) {
+		t.Parallel()
+		ctrl := gomock.NewController(t)
+		mockConn := agentconnmock.NewMockAgentConn(ctrl)
+		chatPlanPath := "/home/coder/.coder/plans/PLAN-123e4567-e89b-12d3-a456-426614174000.md"
+
+		mockConn.EXPECT().
+			ReadFile(gomock.Any(), chatPlanPath, int64(0), int64(32*1024+1)).
+			Return(io.NopCloser(strings.NewReader("# Per-Chat Plan")), "text/markdown", nil)
+
+		storeFile, stored := fakeStoreFile(t)
+		resolvePlanPathCalled := false
+		tool := newProposePlanToolWithPlanPath(
+			t,
+			mockConn,
+			storeFile,
+			func(context.Context) (string, string, error) {
+				resolvePlanPathCalled = true
+				return chatPlanPath, "/home/coder", nil
+			},
+		)
+		resp, err := tool.Run(context.Background(), fantasy.ToolCall{
+			ID:    "call-1",
+			Name:  "propose_plan",
+			Input: `{"path":"` + chatPlanPath + `"}`,
+		})
+		require.NoError(t, err)
+		assert.False(t, resp.IsError)
+		assert.False(t, resolvePlanPathCalled)
+
+		result := decodeProposePlanResponse(t, resp)
+		assert.True(t, result.OK)
+		assert.Equal(t, chatPlanPath, result.Path)
+		assert.Equal(t, []byte("# Per-Chat Plan"), *stored)
+	})
+
+	t.Run("NestedPlanPathAllowedWhenResolverFails", func(t *testing.T) {
+		t.Parallel()
+		ctrl := gomock.NewController(t)
+		mockConn := agentconnmock.NewMockAgentConn(ctrl)
+
+		mockConn.EXPECT().
+			ReadFile(gomock.Any(), "/home/coder/myproject/plan.md", int64(0), int64(32*1024+1)).
+			Return(io.NopCloser(strings.NewReader("# Nested Plan")), "text/markdown", nil)
+
+		storeFile, stored := fakeStoreFile(t)
+		tool := newProposePlanToolWithPlanPath(
+			t,
+			mockConn,
+			storeFile,
+			func(context.Context) (string, string, error) {
+				return "", "", xerrors.New("workspace unavailable")
+			},
+		)
+		resp, err := tool.Run(context.Background(), fantasy.ToolCall{
+			ID:    "call-1",
+			Name:  "propose_plan",
+			Input: `{"path":"/home/coder/myproject/plan.md"}`,
+		})
+		require.NoError(t, err)
+		assert.False(t, resp.IsError)
+
+		result := decodeProposePlanResponse(t, resp)
+		assert.True(t, result.OK)
+		assert.Equal(t, "/home/coder/myproject/plan.md", result.Path)
+		assert.Equal(t, []byte("# Nested Plan"), *stored)
+	})
+
 	t.Run("WorkspaceConnectionError", func(t *testing.T) {
 		t.Parallel()
 		storeFile, _ := fakeStoreFile(t)
@@ -278,16 +473,45 @@ func newProposePlanTool(
 	t *testing.T,
 	mockConn *agentconnmock.MockAgentConn,
 	storeFile func(ctx context.Context, name string, mediaType string, data []byte) (uuid.UUID, error),
+) fantasy.AgentTool {
+	t.Helper()
+	return newProposePlanToolWithPlanPath(t, mockConn, storeFile, nil)
+}
+
+func newProposePlanToolWithPlanPath(
+	t *testing.T,
+	mockConn *agentconnmock.MockAgentConn,
+	storeFile func(ctx context.Context, name string, mediaType string, data []byte) (uuid.UUID, error),
+	resolvePlanPath func(context.Context) (string, string, error),
 ) fantasy.AgentTool {
 	t.Helper()
 	return chattool.ProposePlan(chattool.ProposePlanOptions{
 		GetWorkspaceConn: func(_ context.Context) (workspacesdk.AgentConn, error) {
 			return mockConn, nil
 		},
-		StoreFile: storeFile,
+		ResolvePlanPath: resolvePlanPath,
+		StoreFile:       storeFile,
 	})
 }

+func sharedPlanPathResolvedMessage(requestedPath, planPath string) string {
+	return "the plan path " + requestedPath +
+		" is no longer supported at the home root; use the chat-specific plan path: " + planPath
+}
+
+func planPathVerificationMessage(requestedPath string) string {
+	return "the plan path " + requestedPath +
+		" could not be verified because the workspace is currently unavailable to resolve the chat-specific plan path, try again shortly"
+}
+
+func editFilesBatchRejectedMessage(message string) string {
+	return message + "; no files in this batch were applied"
+}
+
+func relativePlanPathMessage() string {
+	return "plan files must use absolute paths; use the chat-specific absolute plan path"
+}
+
 func fakeStoreFile(t *testing.T) (func(ctx context.Context, name string, mediaType string, data []byte) (uuid.UUID, error), *[]byte) {
 	t.Helper()

@@ -11,6 +11,7 @@ import (

 type WriteFileOptions struct {
 	GetWorkspaceConn func(context.Context) (workspacesdk.AgentConn, error)
+	ResolvePlanPath  func(context.Context) (chatPath string, home string, err error)
 }

 type WriteFileArgs struct {
@@ -30,7 +31,7 @@ func WriteFile(options WriteFileOptions) fantasy.AgentTool {
 			if err != nil {
 				return fantasy.NewTextErrorResponse(err.Error()), nil
 			}
-			return executeWriteFileTool(ctx, conn, args)
+			return executeWriteFileTool(ctx, conn, args, options.ResolvePlanPath)
 		},
 	)
 }
@@ -39,12 +40,28 @@ func executeWriteFileTool(
 	ctx context.Context,
 	conn workspacesdk.AgentConn,
 	args WriteFileArgs,
+	resolvePlanPath func(context.Context) (chatPath string, home string, err error),
 ) (fantasy.ToolResponse, error) {
-	if args.Path == "" {
+	requestedPath := strings.TrimSpace(args.Path)
+	if requestedPath == "" {
 		return fantasy.NewTextErrorResponse("path is required"), nil
 	}

-	if err := conn.WriteFile(ctx, args.Path, strings.NewReader(args.Content)); err != nil {
+	hasPlanFileName := looksLikePlanFileName(requestedPath)
+	if hasPlanFileName && !isAbsolutePath(requestedPath) {
+		return fantasy.NewTextErrorResponse(
+			"plan files must use absolute paths; use the chat-specific absolute plan path",
+		), nil
+	}
+
+	if resolvePlanPath != nil && hasPlanFileName {
+		chatPath, home, err := resolvePlanPath(ctx)
+		if resp, rejected := rejectSharedPlanPath(requestedPath, home, chatPath, err); rejected {
+			return resp, nil
+		}
+	}
+
+	if err := conn.WriteFile(ctx, requestedPath, strings.NewReader(args.Content)); err != nil {
 		return fantasy.NewTextErrorResponse(err.Error()), nil
 	}
 	return toolResponse(map[string]any{"ok": true}), nil
@@ -0,0 +1,321 @@
+package chattool_test
+
+import (
+	"context"
+	"io"
+	"strings"
+	"testing"
+
+	"charm.land/fantasy"
+	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/require"
+	"go.uber.org/mock/gomock"
+	"golang.org/x/xerrors"
+
+	"github.com/coder/coder/v2/coderd/x/chatd/chattool"
+	"github.com/coder/coder/v2/codersdk/workspacesdk"
+	"github.com/coder/coder/v2/codersdk/workspacesdk/agentconnmock"
+)
+
+func TestWriteFile(t *testing.T) {
+	t.Parallel()
+
+	t.Run("RejectsHomeRootPlanVariantsWhenResolvePlanPathIsConfigured", func(t *testing.T) {
+		t.Parallel()
+
+		tests := []struct {
+			name      string
+			requested string
+			home      string
+		}{
+			{
+				name:      "ExactLegacyPath",
+				requested: chattool.LegacySharedPlanPath,
+				home:      "/home/coder",
+			},
+			{
+				name:      "LowercasePlanAtHomeRoot",
+				requested: "/home/coder/plan.md",
+				home:      "/home/coder",
+			},
+			{
+				name:      "MixedCasePlanAtHomeRoot",
+				requested: "/home/coder/Plan.md",
+				home:      "/home/coder",
+			},
+		}
+
+		for _, testCase := range tests {
+			t.Run(testCase.name, func(t *testing.T) {
+				t.Parallel()
+
+				ctrl := gomock.NewController(t)
+				mockConn := agentconnmock.NewMockAgentConn(ctrl)
+				tool := chattool.WriteFile(chattool.WriteFileOptions{
+					GetWorkspaceConn: func(context.Context) (workspacesdk.AgentConn, error) {
+						return mockConn, nil
+					},
+					ResolvePlanPath: func(context.Context) (string, string, error) {
+						return "/home/coder/.coder/plans/PLAN-chat.md", testCase.home, nil
+					},
+				})
+
+				resp, err := tool.Run(context.Background(), fantasy.ToolCall{
+					ID:    "call-1",
+					Name:  "write_file",
+					Input: `{"path":"` + testCase.requested + `","content":"# Plan"}`,
+				})
+				require.NoError(t, err)
+				assert.True(t, resp.IsError)
+				assert.Equal(
+					t,
+					sharedPlanPathResolvedMessage(
+						testCase.requested,
+						"/home/coder/.coder/plans/PLAN-chat.md",
+					),
+					resp.Content,
+				)
+			})
+		}
+	})
+
+	t.Run("RejectsRelativePlanPathsWhenResolvePlanPathIsConfigured", func(t *testing.T) {
+		t.Parallel()
+
+		tests := []struct {
+			name      string
+			requested string
+		}{
+			{
+				name:      "PlainRelativePath",
+				requested: "plan.md",
+			},
+			{
+				name:      "DotSlashRelativePath",
+				requested: "./plan.md",
+			},
+		}
+
+		for _, testCase := range tests {
+			t.Run(testCase.name, func(t *testing.T) {
+				t.Parallel()
+
+				ctrl := gomock.NewController(t)
+				mockConn := agentconnmock.NewMockAgentConn(ctrl)
+				resolvePlanPathCalled := false
+				tool := chattool.WriteFile(chattool.WriteFileOptions{
+					GetWorkspaceConn: func(context.Context) (workspacesdk.AgentConn, error) {
+						return mockConn, nil
+					},
+					ResolvePlanPath: func(context.Context) (string, string, error) {
+						resolvePlanPathCalled = true
+						return "/home/coder/.coder/plans/PLAN-chat.md", "/home/coder", nil
+					},
+				})
+
+				resp, err := tool.Run(context.Background(), fantasy.ToolCall{
+					ID:    "call-1",
+					Name:  "write_file",
+					Input: `{"path":"` + testCase.requested + `","content":"# Plan"}`,
+				})
+				require.NoError(t, err)
+				assert.True(t, resp.IsError)
+				assert.False(t, resolvePlanPathCalled)
+				assert.Equal(t, relativePlanPathMessage(), resp.Content)
+			})
+		}
+	})
+
+	t.Run("RejectsSharedPlanPathWhenResolverFails", func(t *testing.T) {
+		t.Parallel()
+		ctrl := gomock.NewController(t)
+		mockConn := agentconnmock.NewMockAgentConn(ctrl)
+		tool := chattool.WriteFile(chattool.WriteFileOptions{
+			GetWorkspaceConn: func(context.Context) (workspacesdk.AgentConn, error) {
+				return mockConn, nil
+			},
+			ResolvePlanPath: func(context.Context) (string, string, error) {
+				return "", "", xerrors.New("workspace unavailable")
+			},
+		})
+
+		resp, err := tool.Run(context.Background(), fantasy.ToolCall{
+			ID:    "call-1",
+			Name:  "write_file",
+			Input: `{"path":"/home/coder/plan.md","content":"# Plan"}`,
+		})
+		require.NoError(t, err)
+		assert.True(t, resp.IsError)
+		assert.Equal(t, planPathVerificationMessage("/home/coder/plan.md"), resp.Content)
+	})
+
+	t.Run("PerChatPlanPathIsAllowed", func(t *testing.T) {
+		t.Parallel()
+		ctrl := gomock.NewController(t)
+		mockConn := agentconnmock.NewMockAgentConn(ctrl)
+		chatPlanPath := "/home/coder/.coder/plans/PLAN-123e4567-e89b-12d3-a456-426614174000.md"
+		mockConn.EXPECT().
+			WriteFile(gomock.Any(), chatPlanPath, gomock.Any()).
+			DoAndReturn(func(_ context.Context, path string, reader io.Reader) error {
+				data, err := io.ReadAll(reader)
+				require.NoError(t, err)
+				require.Equal(t, chatPlanPath, path)
+				require.Equal(t, "# Plan", string(data))
+				return nil
+			})
+
+		resolvePlanPathCalled := false
+		tool := chattool.WriteFile(chattool.WriteFileOptions{
+			GetWorkspaceConn: func(context.Context) (workspacesdk.AgentConn, error) {
+				return mockConn, nil
+			},
+			ResolvePlanPath: func(context.Context) (string, string, error) {
+				resolvePlanPathCalled = true
+				return chatPlanPath, "/home/coder", nil
+			},
+		})
+
+		resp, err := tool.Run(context.Background(), fantasy.ToolCall{
+			ID:    "call-1",
+			Name:  "write_file",
+			Input: `{"path":"` + chatPlanPath + `","content":"# Plan"}`,
+		})
+		require.NoError(t, err)
+		assert.False(t, resp.IsError)
+		assert.False(t, resolvePlanPathCalled)
+		assert.Equal(t, `{"ok":true}`, strings.TrimSpace(resp.Content))
+	})
+
+	t.Run("NestedPlanPathAllowedWhenResolverFails", func(t *testing.T) {
+		t.Parallel()
+		ctrl := gomock.NewController(t)
+		mockConn := agentconnmock.NewMockAgentConn(ctrl)
+		mockConn.EXPECT().
+			WriteFile(gomock.Any(), "/home/coder/myproject/plan.md", gomock.Any()).
+			DoAndReturn(func(_ context.Context, path string, reader io.Reader) error {
+				data, err := io.ReadAll(reader)
+				require.NoError(t, err)
+				require.Equal(t, "/home/coder/myproject/plan.md", path)
+				require.Equal(t, "# Plan", string(data))
+				return nil
+			})
+
+		tool := chattool.WriteFile(chattool.WriteFileOptions{
+			GetWorkspaceConn: func(context.Context) (workspacesdk.AgentConn, error) {
+				return mockConn, nil
+			},
+			ResolvePlanPath: func(context.Context) (string, string, error) {
+				return "", "", xerrors.New("workspace unavailable")
+			},
+		})
+
+		resp, err := tool.Run(context.Background(), fantasy.ToolCall{
+			ID:    "call-1",
+			Name:  "write_file",
+			Input: `{"path":"/home/coder/myproject/plan.md","content":"# Plan"}`,
+		})
+		require.NoError(t, err)
+		assert.False(t, resp.IsError)
+		assert.Equal(t, `{"ok":true}`, strings.TrimSpace(resp.Content))
+	})
+
+	t.Run("NestedPlanPathUnderHomeIsAllowed", func(t *testing.T) {
+		t.Parallel()
+		ctrl := gomock.NewController(t)
+		mockConn := agentconnmock.NewMockAgentConn(ctrl)
+		mockConn.EXPECT().
+			WriteFile(gomock.Any(), "/home/coder/myproject/plan.md", gomock.Any()).
+			DoAndReturn(func(_ context.Context, path string, reader io.Reader) error {
+				data, err := io.ReadAll(reader)
+				require.NoError(t, err)
+				require.Equal(t, "/home/coder/myproject/plan.md", path)
+				require.Equal(t, "# Plan", string(data))
+				return nil
+			})
+
+		planPathCalled := false
+		tool := chattool.WriteFile(chattool.WriteFileOptions{
+			GetWorkspaceConn: func(context.Context) (workspacesdk.AgentConn, error) {
+				return mockConn, nil
+			},
+			ResolvePlanPath: func(context.Context) (string, string, error) {
+				planPathCalled = true
+				return "/home/coder/.coder/plans/PLAN-chat.md", "/home/coder", nil
+			},
+		})
+
+		resp, err := tool.Run(context.Background(), fantasy.ToolCall{
+			ID:    "call-1",
+			Name:  "write_file",
+			Input: `{"path":"/home/coder/myproject/plan.md","content":"# Plan"}`,
+		})
+		require.NoError(t, err)
+		assert.False(t, resp.IsError)
+		assert.True(t, planPathCalled)
+		assert.Equal(t, `{"ok":true}`, strings.TrimSpace(resp.Content))
+	})
+
+	t.Run("AllowsNonSharedPath", func(t *testing.T) {
+		t.Parallel()
+		ctrl := gomock.NewController(t)
+		mockConn := agentconnmock.NewMockAgentConn(ctrl)
+		mockConn.EXPECT().
+			WriteFile(gomock.Any(), "/home/dev/my-plan.md", gomock.Any()).
+			DoAndReturn(func(_ context.Context, path string, reader io.Reader) error {
+				data, err := io.ReadAll(reader)
+				require.NoError(t, err)
+				require.Equal(t, "/home/dev/my-plan.md", path)
+				require.Equal(t, "# Plan", string(data))
+				return nil
+			})
+
+		resolvePlanPathCalled := false
+		tool := chattool.WriteFile(chattool.WriteFileOptions{
+			GetWorkspaceConn: func(context.Context) (workspacesdk.AgentConn, error) {
+				return mockConn, nil
+			},
+			ResolvePlanPath: func(context.Context) (string, string, error) {
+				resolvePlanPathCalled = true
+				return "", "", xerrors.New("should not be called")
+			},
+		})
+
+		resp, err := tool.Run(context.Background(), fantasy.ToolCall{
+			ID:    "call-1",
+			Name:  "write_file",
+			Input: `{"path":"/home/dev/my-plan.md","content":"# Plan"}`,
+		})
+		require.NoError(t, err)
+		assert.False(t, resp.IsError)
+		assert.False(t, resolvePlanPathCalled)
+		assert.Equal(t, `{"ok":true}`, strings.TrimSpace(resp.Content))
+	})
+
+	t.Run("AllowsSharedPlanPathWhenResolvePlanPathIsNil", func(t *testing.T) {
+		t.Parallel()
+		ctrl := gomock.NewController(t)
+		mockConn := agentconnmock.NewMockAgentConn(ctrl)
+		mockConn.EXPECT().
+			WriteFile(gomock.Any(), chattool.LegacySharedPlanPath, gomock.Any()).
+			DoAndReturn(func(_ context.Context, _ string, reader io.Reader) error {
+				data, err := io.ReadAll(reader)
+				require.NoError(t, err)
+				require.Equal(t, "# Plan", string(data))
+				return nil
+			})
+
+		tool := chattool.WriteFile(chattool.WriteFileOptions{
+			GetWorkspaceConn: func(context.Context) (workspacesdk.AgentConn, error) {
+				return mockConn, nil
+			},
+		})
+
+		resp, err := tool.Run(context.Background(), fantasy.ToolCall{
+			ID:    "call-1",
+			Name:  "write_file",
+			Input: `{"path":"` + chattool.LegacySharedPlanPath + `","content":"# Plan"}`,
+		})
+		require.NoError(t, err)
+		assert.False(t, resp.IsError)
+	})
+}