diff --git a/cmd/serve_test.go b/cmd/serve_test.go
index 8777e112..8ca21f56 100644
--- a/cmd/serve_test.go
+++ b/cmd/serve_test.go
@@ -1246,6 +1246,18 @@ func TestParseResponsesInput_FileUploadSavesToDisk(t *testing.T) {
 	if strings.Contains(msg.Parts[0].Text, dataHome) || strings.Contains(msg.Parts[0].Text, entries[0].Name()) {
 		t.Fatalf("parts[0].text leaks upload path: %q", msg.Parts[0].Text)
 	}
+
+	stored := session.NewMessage("sess_upload", msg, 0)
+	partsJSON, err := stored.PartsJSONForStorage(true)
+	if err != nil {
+		t.Fatalf("PartsJSONForStorage: %v", err)
+	}
+	if strings.Contains(partsJSON, b64) {
+		t.Fatalf("storage parts json retained file base64 despite strip option: %s", partsJSON)
+	}
+	if !strings.Contains(partsJSON, msg.Parts[0].FilePath) || !strings.Contains(partsJSON, "doc.pdf") || !strings.Contains(partsJSON, "application/pdf") {
+		t.Fatalf("storage parts json lost file path or metadata: %s", partsJSON)
+	}
 }
 
 func TestParseResponsesInput_TextFileUploadEmbedsFallback(t *testing.T) {
diff --git a/internal/llm/responses_api.go b/internal/llm/responses_api.go
index d2061b66..94f0821d 100644
--- a/internal/llm/responses_api.go
+++ b/internal/llm/responses_api.go
@@ -4,11 +4,15 @@ import (
 	"bufio"
 	"bytes"
 	"context"
+	"encoding/base64"
 	"encoding/json"
 	"errors"
 	"fmt"
 	"io"
+	"mime"
 	"net/http"
+	"os"
+	"path/filepath"
 	"strings"
 	"sync"
 	"time"
@@ -407,20 +411,20 @@ func buildResponsesMessageItems(role string, parts []Part, policy *FileUploadPol
 				})
 			}
 		case PartFile:
-			if part.FileData != nil && part.FileData.Base64 != "" && responseNativeFileAllowed(part.FileData, policy) {
+			if fileData, ok := responseNativeFileData(part, policy); ok {
 				flushText()
-				filename := strings.TrimSpace(part.FileData.Filename)
+				filename := strings.TrimSpace(fileData.Filename)
 				if filename == "" {
 					filename = "upload"
 				}
-				mediaType := NormalizeMediaType(part.FileData.MediaType)
+				mediaType := NormalizeMediaType(fileData.MediaType)
 				if mediaType == "" {
 					mediaType = "application/octet-stream"
 				}
 				fileParts := []ResponsesContentPart{{
 					Type:     "input_file",
 					Filename: filename,
-					FileData: fmt.Sprintf("data:%s;base64,%s", mediaType, part.FileData.Base64),
+					FileData: fmt.Sprintf("data:%s;base64,%s", mediaType, fileData.Base64),
 				}}
 				items = append(items, ResponsesInputItem{
 					Type:    "message",
@@ -463,6 +467,55 @@ func effectiveResponsesFilePolicy(policy *FileUploadPolicy) FileUploadPolicy {
 	return *policy
 }
 
+func responseNativeFileData(part Part, policy *FileUploadPolicy) (*ToolFileData, bool) {
+	if part.FileData == nil {
+		return nil, false
+	}
+	fileData := *part.FileData
+	if strings.TrimSpace(fileData.Base64) == "" {
+		var ok bool
+		fileData, ok = hydrateResponseFileDataFromPath(part, fileData, policy)
+		if !ok {
+			return nil, false
+		}
+	}
+	if !responseNativeFileAllowed(&fileData, policy) {
+		return nil, false
+	}
+	return &fileData, true
+}
+
+func hydrateResponseFileDataFromPath(part Part, fileData ToolFileData, policy *FileUploadPolicy) (ToolFileData, bool) {
+	path := strings.TrimSpace(part.FilePath)
+	if path == "" || !isTermLLMUploadPath(path) {
+		return fileData, false
+	}
+	info, err := os.Stat(path)
+	if err != nil || info.IsDir() || info.Size() <= 0 || info.Size() > defaultFileUploadMaxBytes {
+		return fileData, false
+	}
+	fileData.SizeBytes = info.Size()
+	if strings.TrimSpace(fileData.MediaType) == "" {
+		fileData.MediaType = strings.TrimSpace(mime.TypeByExtension(strings.ToLower(filepath.Ext(path))))
+	}
+	if strings.TrimSpace(fileData.MediaType) == "" {
+		fileData.MediaType = "application/octet-stream"
+	}
+	if strings.TrimSpace(fileData.Filename) == "" {
+		fileData.Filename = filepath.Base(path)
+	}
+	active := effectiveResponsesFilePolicy(policy)
+	if !active.AllowsNative(fileData.MediaType, fileData.SizeBytes) {
+		return fileData, false
+	}
+	data, err := os.ReadFile(path)
+	if err != nil || len(data) == 0 || int64(len(data)) > defaultFileUploadMaxBytes {
+		return fileData, false
+	}
+	fileData.Base64 = base64.StdEncoding.EncodeToString(data)
+	return fileData, true
+}
+
 func responseNativeFileAllowed(file *ToolFileData, policy *FileUploadPolicy) bool {
 	if file == nil || strings.TrimSpace(file.Base64) == "" {
 		return false
diff --git a/internal/llm/responses_api_test.go b/internal/llm/responses_api_test.go
index 72da9fe0..4f491cda 100644
--- a/internal/llm/responses_api_test.go
+++ b/internal/llm/responses_api_test.go
@@ -9,6 +9,8 @@ import (
 	"fmt"
 	"io"
 	"net/http"
+	"os"
+	"path/filepath"
 	"strings"
 	"testing"
 	"time"
@@ -145,6 +147,47 @@ func TestBuildResponsesInput_FilePolicyAllowsNativePDF(t *testing.T) {
 	}
 }
 
+func TestBuildResponsesInput_FilePolicyHydratesPathOnlyNativePDF(t *testing.T) {
+	dataHome := t.TempDir()
+	t.Setenv("XDG_DATA_HOME", dataHome)
+	uploadsDir := filepath.Join(dataHome, "term-llm", "uploads")
+	if err := os.MkdirAll(uploadsDir, 0o700); err != nil {
+		t.Fatalf("mkdir uploads: %v", err)
+	}
+	filePath := filepath.Join(uploadsDir, "doc.pdf")
+	if err := os.WriteFile(filePath, []byte("file-bytes"), 0o600); err != nil {
+		t.Fatalf("write upload: %v", err)
+	}
+	messages := []Message{{Role: RoleUser, Parts: []Part{{
+		Type: PartFile,
+		Text: "[User uploaded file: doc.pdf — saved locally]",
+		FileData: &ToolFileData{
+			MediaType: "application/pdf",
+			Filename:  "doc.pdf",
+			SizeBytes: int64(len("file-bytes")),
+		},
+		FilePath: filePath,
+	}}}}
+
+	input := BuildResponsesInput(messages)
+	if len(input) != 1 {
+		t.Fatalf("len(input) = %d, want 1", len(input))
+	}
+	parts, ok := input[0].Content.([]ResponsesContentPart)
+	if !ok || len(parts) != 1 {
+		t.Fatalf("content = %#v, want one content part", input[0].Content)
+	}
+	if parts[0].Type != "input_file" || parts[0].Filename != "doc.pdf" {
+		t.Fatalf("file part = %#v", parts[0])
+	}
+	if parts[0].FileData != "data:application/pdf;base64,ZmlsZS1ieXRlcw==" {
+		t.Fatalf("file_data = %q", parts[0].FileData)
+	}
+	if strings.Contains(fmt.Sprint(input[0].Content), filePath) {
+		t.Fatalf("native file content leaked local path: %#v", input[0].Content)
+	}
+}
+
 func TestBuildResponsesInput_FilePolicyFallsBackToTextWhenNativeDisabled(t *testing.T) {
 	policy := DefaultPortableTextFileUploadPolicy()
 	messages := []Message{{Role: RoleUser, Parts: []Part{{
diff --git a/internal/session/file_upload_test.go b/internal/session/file_upload_test.go
index 945e8898..d7e270cb 100644
--- a/internal/session/file_upload_test.go
+++ b/internal/session/file_upload_test.go
@@ -116,6 +116,59 @@ func TestMessageStripsImageBase64WhenStorageOptionEnabled(t *testing.T) {
 	}
 }
 
+func TestMessageStripsUploadedFileBase64WhenStorageOptionEnabled(t *testing.T) {
+	dataHome := t.TempDir()
+	t.Setenv("XDG_DATA_HOME", dataHome)
+	uploadPath := filepath.Join(dataHome, "term-llm", "uploads", "doc.pdf")
+	if err := os.MkdirAll(filepath.Dir(uploadPath), 0o700); err != nil {
+		t.Fatalf("mkdir uploads: %v", err)
+	}
+	if err := os.WriteFile(uploadPath, []byte("file-bytes"), 0o600); err != nil {
+		t.Fatalf("write upload: %v", err)
+	}
+	const b64 = "ZmlsZS1ieXRlcw=="
+	msg := NewMessage("sess_test", llm.Message{Role: llm.RoleUser, Parts: []llm.Part{{
+		Type: llm.PartFile,
+		Text: "[User uploaded file: doc.pdf — saved locally]\n\n",
+		FileData: &llm.ToolFileData{
+			MediaType: "application/pdf",
+			Base64:    b64,
+			Filename:  "doc.pdf",
+			SizeBytes: int64(len("file-bytes")),
+		},
+		FilePath: uploadPath,
+	}}}, 0)
+
+	if msg.Parts[0].FileData == nil || msg.Parts[0].FileData.Base64 != b64 {
+		t.Fatal("in-memory message should preserve file base64 for the active request")
+	}
+	partsJSON, err := msg.PartsJSONForStorage(true)
+	if err != nil {
+		t.Fatalf("PartsJSONForStorage: %v", err)
+	}
+	if strings.Contains(partsJSON, b64) {
+		t.Fatalf("storage parts json retained file base64 despite strip option: %s", partsJSON)
+	}
+
+	var roundTrip Message
+	if err := roundTrip.SetPartsFromJSON(partsJSON); err != nil {
+		t.Fatalf("SetPartsFromJSON: %v", err)
+	}
+	part := roundTrip.Parts[0]
+	if part.FilePath != uploadPath {
+		t.Fatalf("FilePath = %q, want preserved path", part.FilePath)
+	}
+	if part.FileData == nil {
+		t.Fatal("FileData is nil, want file metadata preserved")
+	}
+	if part.FileData.Base64 != "" {
+		t.Fatalf("FileData.Base64 = %q, want stripped", part.FileData.Base64)
+	}
+	if part.FileData.MediaType != "application/pdf" || part.FileData.Filename != "doc.pdf" || part.FileData.SizeBytes != int64(len("file-bytes")) {
+		t.Fatalf("FileData metadata = %+v, want media type/filename/size preserved", part.FileData)
+	}
+}
+
 func TestSQLiteStoreStripImageBase64Config(t *testing.T) {
 	ctx := context.Background()
 	dataHome := t.TempDir()
diff --git a/internal/session/types.go b/internal/session/types.go
index 9024213e..5388dd46 100644
--- a/internal/session/types.go
+++ b/internal/session/types.go
@@ -285,6 +285,17 @@ func partsForStorage(parts []llm.Part) []llm.Part {
 			out = append(out, copyPart)
 			continue
 		}
+		if part.Type == llm.PartFile && isSessionUploadPath(part.FilePath) && part.FileData != nil && strings.TrimSpace(part.FileData.Base64) != "" {
+			if out == nil {
+				out = append([]llm.Part(nil), parts[:i]...)
+			}
+			copyPart := part
+			fileData := *part.FileData
+			fileData.Base64 = ""
+			copyPart.FileData = &fileData
+			out = append(out, copyPart)
+			continue
+		}
 		if out != nil {
 			out = append(out, part)
 		}