diff --git a/handlers/guest_links_test.go b/handlers/guest_links_test.go
index b1ce0838..96338c9d 100644
--- a/handlers/guest_links_test.go
+++ b/handlers/guest_links_test.go
@@ -57,6 +57,40 @@ func TestGuestLinksPostAcceptsValidRequest(t *testing.T) {
 				MaxFileUploads: makeGuestUploadCountLimit(1),
 			},
 		},
+		{
+			description: "guest file expires in 1 day",
+			payload: `{
+					"label": "For my good pal, Maurice",
+					"urlExpirationTime":"2030-01-02T03:04:25Z",
+					"fileLifetime":"24h0m0s",
+					"maxFileBytes": 1048576,
+					"maxFileUploads": 1
+				}`,
+			expected: picoshare.GuestLink{
+				Label:          picoshare.GuestLinkLabel("For my good pal, Maurice"),
+				UrlExpires:     mustParseExpirationTime("2030-01-02T03:04:25Z"),
+				FileLifetime:   picoshare.NewFileLifetimeInDays(1),
+				MaxFileBytes:   makeGuestUploadMaxFileBytes(1048576),
+				MaxFileUploads: makeGuestUploadCountLimit(1),
+			},
+		},
+		{
+			description: "guest file expires in 30 day",
+			payload: `{
+					"label": "For my good pal, Maurice",
+					"urlExpirationTime":"2030-01-02T03:04:25Z",
+					"fileLifetime":"720h0m0s",
+					"maxFileBytes": 1048576,
+					"maxFileUploads": 1
+				}`,
+			expected: picoshare.GuestLink{
+				Label:          picoshare.GuestLinkLabel("For my good pal, Maurice"),
+				UrlExpires:     mustParseExpirationTime("2030-01-02T03:04:25Z"),
+				FileLifetime:   picoshare.NewFileLifetimeInDays(30),
+				MaxFileBytes:   makeGuestUploadMaxFileBytes(1048576),
+				MaxFileUploads: makeGuestUploadCountLimit(1),
+			},
+		},
 	} {
 		t.Run(tt.description, func(t *testing.T) {
 			dataStore := test_sqlite.New()
diff --git a/handlers/templates/pages/guest-link-index.html b/handlers/templates/pages/guest-link-index.html
index a6edcae4..d34f667f 100644
--- a/handlers/templates/pages/guest-link-index.html
+++ b/handlers/templates/pages/guest-link-index.html
@@ -144,7 +144,7 @@ <h1 class="title">Guest Links</h1>
               {{ formatExpiration .UrlExpires }}
             </td>
             <td class="is-vcentered expiration">
-              {{ formatFileExpiration .FileLifetime }}
+              {{ .FileLifetime.FriendlyName }}
             </td>
             <td class="is-vcentered">
               {{ formatSizeLimit .MaxFileBytes }}
diff --git a/handlers/upload_test.go b/handlers/upload_test.go
index 07bd1d5e..1e86cb77 100644
--- a/handlers/upload_test.go
+++ b/handlers/upload_test.go
@@ -5,6 +5,7 @@ import (
 	"bytes"
 	"encoding/json"
 	"io"
+	"math"
 	"mime/multipart"
 	"net/http"
 	"net/http/httptest"
@@ -280,9 +281,10 @@ func TestGuestUpload(t *testing.T) {
 		{
 			description: "valid upload to guest link",
 			guestLinkInStore: picoshare.GuestLink{
-				ID:         picoshare.GuestLinkID("abcdefgh23456789"),
-				Created:    mustParseTime("2022-01-01T00:00:00Z"),
-				UrlExpires: mustParseExpirationTime("2030-01-02T03:04:25Z"),
+				ID:           picoshare.GuestLinkID("abcdefgh23456789"),
+				Created:      mustParseTime("2022-01-01T00:00:00Z"),
+				UrlExpires:   mustParseExpirationTime("2030-01-02T03:04:25Z"),
+				FileLifetime: picoshare.FileLifetimeInfinite,
 			},
 			guestLinkID: "abcdefgh23456789",
 			status:      http.StatusOK,
@@ -378,6 +380,28 @@ func TestGuestUpload(t *testing.T) {
 			guestLinkID: "abcdefgh23456789",
 			status:      http.StatusBadRequest,
 		},
+		{
+			description: "guest file expires in 1 day",
+			guestLinkInStore: picoshare.GuestLink{
+				ID:           picoshare.GuestLinkID("abcdefgh23456789"),
+				Created:      mustParseTime("2022-01-01T00:00:00Z"),
+				UrlExpires:   mustParseExpirationTime("2030-01-02T03:04:25Z"),
+				FileLifetime: picoshare.NewFileLifetimeInDays(1),
+			},
+			guestLinkID: "abcdefgh23456789",
+			status:      http.StatusOK,
+		},
+		{
+			description: "guest file expires in 365 day",
+			guestLinkInStore: picoshare.GuestLink{
+				ID:           picoshare.GuestLinkID("abcdefgh23456789"),
+				Created:      mustParseTime("2022-01-01T00:00:00Z"),
+				UrlExpires:   mustParseExpirationTime("2030-01-02T03:04:25Z"),
+				FileLifetime: picoshare.NewFileLifetimeInDays(365),
+			},
+			guestLinkID: "abcdefgh23456789",
+			status:      http.StatusOK,
+		},
 	} {
 		t.Run(tt.description, func(t *testing.T) {
 			store := test_sqlite.New()
@@ -441,13 +465,21 @@ func TestGuestUpload(t *testing.T) {
 			}
 
 			// Guest uploads never expire.
-			// if got, want := entry.Expires, picoshare.NeverExpire; got != want {
-			// 	t.Errorf("expiration=%v, want=%v", got, want)
-			// }
+			if got, want := convertExpirationTimeToFileLifetime(entry.Expires), tt.guestLinkInStore.FileLifetime; got != want {
+				t.Errorf("expiration=%v, want=%v", got, want)
+			}
 		})
 	}
 }
 
+func convertExpirationTimeToFileLifetime(et picoshare.ExpirationTime) picoshare.FileLifetime {
+	if et == picoshare.NeverExpire {
+		return picoshare.FileLifetimeInfinite
+	}
+	delta := math.Round(time.Until(time.Time(et)).Hours() / 24)
+	return picoshare.NewFileLifetimeInDays(uint16(delta))
+}
+
 func createMultipartFormBody(filename, note string, r io.Reader) (io.Reader, string) {
 	var b bytes.Buffer
 	bw := bufio.NewWriter(&b)
diff --git a/handlers/views.go b/handlers/views.go
index 4ae498e8..42e26dd0 100644
--- a/handlers/views.go
+++ b/handlers/views.go
@@ -87,17 +87,6 @@ func (s Server) guestLinkIndexGet() http.HandlerFunc {
 			}
 			return fmt.Sprintf("%s (%.0f days%s)", t.Format(time.DateOnly), math.Abs(delta.Hours())/24, suffix)
 		},
-		"formatFileExpiration": func(flt picoshare.FileLifetime) string {
-			if flt == picoshare.FileLifetimeInfinite {
-				return "Never"
-			}
-
-			letterS := "s"
-			if flt.Duration().Hours() < 25 {
-				letterS = ""
-			}
-			return fmt.Sprintf("After %.0f day%s", math.Abs(flt.Duration().Hours()/24), letterS)
-		},
 		"isActive": func(gl picoshare.GuestLink) bool {
 			return gl.IsActive()
 		},