diff --git a/fileglancer/alembic/versions/20b763c28c4f_add_url_prefix_to_proxied_paths.py b/fileglancer/alembic/versions/20b763c28c4f_add_url_prefix_to_proxied_paths.py
new file mode 100644
index 000000000..0a507d6e7
--- /dev/null
+++ b/fileglancer/alembic/versions/20b763c28c4f_add_url_prefix_to_proxied_paths.py
@@ -0,0 +1,35 @@
+"""add url_prefix to proxied_paths
+
+Revision ID: 20b763c28c4f
+Revises: a3d7cc6e95e8
+Create Date: 2026-04-09 16:11:10.155619
+
+"""
+from alembic import op
+import sqlalchemy as sa
+
+
+# revision identifiers, used by Alembic.
+revision = '20b763c28c4f'
+down_revision = 'a3d7cc6e95e8'
+branch_labels = None
+depends_on = None
+
+
+def upgrade() -> None:
+    op.add_column('proxied_paths', sa.Column('url_prefix', sa.String(), server_default='', nullable=False))
+    # Backfill: set url_prefix to basename of path for existing rows
+    proxied_paths = sa.table('proxied_paths', sa.column('path', sa.String), sa.column('url_prefix', sa.String))
+    conn = op.get_bind()
+    rows = conn.execute(sa.select(proxied_paths.c.path).distinct()).fetchall()
+    for (path,) in rows:
+        basename = path.rsplit('/', 1)[-1] if '/' in path else path
+        conn.execute(
+            proxied_paths.update()
+            .where(proxied_paths.c.path == path)
+            .values(url_prefix=basename)
+        )
+
+
+def downgrade() -> None:
+    op.drop_column('proxied_paths', 'url_prefix')
\ No newline at end of file
diff --git a/fileglancer/database.py b/fileglancer/database.py
index f1f885923..0cdf458d8 100644
--- a/fileglancer/database.py
+++ b/fileglancer/database.py
@@ -95,6 +95,7 @@ class ProxiedPathDB(Base):
     sharing_name = Column(String, nullable=False)
     fsp_name = Column(String, nullable=False)
     path = Column(String, nullable=False)
+    url_prefix = Column(String, nullable=False, server_default="")
     created_at = Column(DateTime, nullable=False, default=lambda: datetime.now(UTC))
     updated_at = Column(DateTime, nullable=False, default=lambda: datetime.now(UTC), onupdate=lambda: datetime.now(UTC))
 
@@ -589,7 +590,7 @@ def _validate_proxied_path(session: Session, fsp_name: str, path: str) -> None:
         raise ValueError(f"Path {path} is not accessible relative to {fsp_name}")
 
 
-def create_proxied_path(session: Session, username: str, sharing_name: str, fsp_name: str, path: str) -> ProxiedPathDB:
+def create_proxied_path(session: Session, username: str, sharing_name: str, fsp_name: str, path: str, url_prefix: str = "") -> ProxiedPathDB:
     """Create a new proxied path"""
     _validate_proxied_path(session, fsp_name, path)
 
@@ -601,6 +602,7 @@ def create_proxied_path(session: Session, username: str, sharing_name: str, fsp_
         sharing_name=sharing_name,
         fsp_name=fsp_name,
         path=path,
+        url_prefix=url_prefix,
         created_at=now,
         updated_at=now
     )
@@ -614,6 +616,7 @@ def create_proxied_path(session: Session, username: str, sharing_name: str, fsp_
     return proxied_path
 
 
+
 def update_proxied_path(session: Session,
                         username: str,
                         sharing_key: str,
@@ -630,6 +633,7 @@ def update_proxied_path(session: Session,
 
     if new_sharing_name:
         proxied_path.sharing_name = new_sharing_name
+        proxied_path.url_prefix = new_sharing_name
 
     if new_fsp_name:
         proxied_path.fsp_name = new_fsp_name
diff --git a/fileglancer/model.py b/fileglancer/model.py
index 2ff0e0c47..553ab178c 100644
--- a/fileglancer/model.py
+++ b/fileglancer/model.py
@@ -135,7 +135,7 @@ class ProxiedPath(BaseModel):
         description="The sharing key is part of the URL proxy path. It is used to uniquely identify the proxied path."
     )
     sharing_name: str = Field(
-        description="The sharing path is part of the URL proxy path. It is mainly used to provide file extension information to the client."
+        description="A display-only label for the data link. Does not appear in the URL."
     )
     path: str = Field(
         description="The path relative to the file share path mount point"
@@ -149,6 +149,9 @@ class ProxiedPath(BaseModel):
     updated_at: datetime = Field(
         description="When this proxied path was last updated"
     )
+    url_prefix: str = Field(
+        description="The URL path prefix that appears after the sharing key in the proxy URL"
+    )
     url: Optional[HttpUrl] = Field(
         description="The URL for accessing the data via the proxy",
         default=None
diff --git a/fileglancer/server.py b/fileglancer/server.py
index de84bd50e..899cc423c 100644
--- a/fileglancer/server.py
+++ b/fileglancer/server.py
@@ -1,5 +1,6 @@
 import logging
 import os
+import re
 import sys
 import pwd
 import grp
@@ -95,7 +96,7 @@ def _convert_external_bucket(db_bucket: db.ExternalBucketDB) -> ExternalBucket:
 def _convert_proxied_path(db_path: db.ProxiedPathDB, external_proxy_url: Optional[HttpUrl]) -> ProxiedPath:
     """Convert a database ProxiedPathDB model to a Pydantic ProxiedPath model"""
     if external_proxy_url:
-        url = f"{external_proxy_url}/{db_path.sharing_key}/{quote(db_path.sharing_name)}"
+        url = f"{external_proxy_url}/{db_path.sharing_key}/{quote(db_path.url_prefix, safe='/')}"
     else:
         logger.warning(f"No external proxy URL was provided, proxy links will not be available.")
         url = None
@@ -105,12 +106,33 @@ def _convert_proxied_path(db_path: db.ProxiedPathDB, external_proxy_url: Optiona
         sharing_name=db_path.sharing_name,
         fsp_name=db_path.fsp_name,
         path=db_path.path,
+        url_prefix=db_path.url_prefix,
         created_at=db_path.created_at,
         updated_at=db_path.updated_at,
         url=url
     )
 
 
+# Regex: allow unreserved URI chars (RFC 3986), plus / for path separators and common safe chars
+_VALID_URL_PREFIX_RE = re.compile(r'^[A-Za-z0-9\-._~/!@$&\'()*+,;:=%]+$')
+
+
+def _validate_url_prefix(url_prefix: str) -> None:
+    """Validate that a url_prefix is non-empty and contains only URL-safe characters."""
+    if not url_prefix or not url_prefix.strip():
+        raise HTTPException(status_code=400, detail="Data link name must not be empty")
+    if not _VALID_URL_PREFIX_RE.match(url_prefix):
+        invalid_chars = set(c for c in url_prefix if not re.match(r"[A-Za-z0-9\-._~/!@$&'()*+,;:=]", c))
+        raise HTTPException(
+            status_code=400,
+            detail=f"Data link name contains invalid URL characters: {' '.join(sorted(invalid_chars))}"
+        )
+    if url_prefix.startswith('/') or url_prefix.endswith('/'):
+        raise HTTPException(status_code=400, detail="Data link name must not start or end with /")
+    if '//' in url_prefix:
+        raise HTTPException(status_code=400, detail="Data link name must not contain consecutive slashes")
+
+
 def _convert_ticket(db_ticket: db.TicketDB) -> Ticket:
     return Ticket(
         username=db_ticket.username,
@@ -199,29 +221,43 @@ def _get_user_context(username: str) -> UserContext:
             return CurrentUserContext()
 
 
-    def _get_file_proxy_client(sharing_key: str, sharing_name: str) -> Tuple[FileProxyClient, UserContext] | Tuple[Response, None]:
+    def _get_file_proxy_client(sharing_key: str, captured_path: str) -> Tuple[FileProxyClient | Response, UserContext | None, str]:
+        """Resolve a sharing key and captured path to a FileProxyClient.
+
+        Returns (client, user_context, subpath) on success, or (error_response, None, "") on failure.
+        """
+        def try_strip_prefix(captured: str, prefix: str) -> str | None:
+            if captured == prefix:
+                return ""
+            if captured.startswith(prefix + "/"):
+                return captured[len(prefix) + 1:]
+            return None
+
         with db.get_db_session(settings.db_url) as session:
 
             proxied_path = db.get_proxied_path_by_sharing_key(session, sharing_key)
             if not proxied_path:
-                return get_nosuchbucket_response(sharing_name), None
-
-            # Vol-E viewer sends URLs with literal % characters (not URL-encoded)
-            # FastAPI automatically decodes path parameters - % chars are treated as escapes, creating a garbled sharing_name if they're present
-            # We therefore need to handle two cases:
-            #   1. Properly encoded requests (sharing_name matches DB value of proxied_path.sharing_name)
-            #   2. Vol-E's unencoded requests (unquote(proxied_path.sharing_name) matches the garbled request value)
-            if proxied_path.sharing_name != sharing_name and unquote(proxied_path.sharing_name) != sharing_name:
-                return get_error_response(404, "NoSuchKey", f"Sharing name mismatch for sharing key {sharing_key}", sharing_name), None
+                return get_nosuchbucket_response(captured_path), None, ""
+
+            # Match captured_path against the stored url_prefix.
+            # The unquote() fallback handles clients like Vol-E viewer that send URLs
+            # with literal % characters instead of proper URL encoding — FastAPI
+            # auto-decodes path params, so we need to match the decoded form too.
+            subpath = try_strip_prefix(captured_path, proxied_path.url_prefix)
+            if subpath is None:
+                subpath = try_strip_prefix(captured_path, unquote(proxied_path.url_prefix))
+            if subpath is None:
+                return get_error_response(404, "NoSuchKey", f"Path mismatch for sharing key {sharing_key}", captured_path), None, ""
 
             fsp = db.get_file_share_path(session, proxied_path.fsp_name)
             if not fsp:
-                return get_error_response(400, "InvalidArgument", f"File share path {proxied_path.fsp_name} not found", sharing_name), None
+                return get_error_response(400, "InvalidArgument", f"File share path {proxied_path.fsp_name} not found", captured_path), None, ""
             # Expand ~ to user's home directory before constructing the mount path
             expanded_mount_path = os.path.expanduser(fsp.mount_path)
             mount_path = f"{expanded_mount_path}/{proxied_path.path}"
+            target_name = captured_path.rsplit('/', 1)[-1] if captured_path else os.path.basename(proxied_path.path)
             # Use 256KB buffer for better performance on network filesystems
-            return FileProxyClient(proxy_kwargs={'target_name': sharing_name}, path=mount_path, buffer_size=256*1024), _get_user_context(proxied_path.username)
+            return FileProxyClient(proxy_kwargs={'target_name': target_name}, path=mount_path, buffer_size=256*1024), _get_user_context(proxied_path.username), subpath
 
 
     @asynccontextmanager
@@ -849,14 +885,20 @@ async def delete_neuroglancer_short_link(short_key: str = Path(..., description=
               description="Create a new proxied path")
     async def create_proxied_path(fsp_name: str = Query(..., description="The name of the file share path that this proxied path is associated with"),
                                   path: str = Query(..., description="The path relative to the file share path mount point"),
+                                  url_prefix: Optional[str] = Query(None, description="The URL path prefix after the sharing key. Defaults to basename of path."),
                                   username: str = Depends(get_current_user)):
 
-        sharing_name = os.path.basename(path)
-        logger.info(f"Creating proxied path for {username} with sharing name {sharing_name} and fsp_name {fsp_name} and path {path}")
+        if url_prefix is None:
+            url_prefix = quote(os.path.basename(path), safe='/')
+        elif not _VALID_URL_PREFIX_RE.match(url_prefix):
+            url_prefix = quote(url_prefix, safe='/')
+        _validate_url_prefix(url_prefix)
+        sharing_name = url_prefix
+        logger.info(f"Creating proxied path for {username} with sharing name {sharing_name} and fsp_name {fsp_name} and path {path} (url_prefix={url_prefix})")
         with db.get_db_session(settings.db_url) as session:
             with _get_user_context(username): # Necessary to validate the user can access the proxied path
                 try:
-                    new_path = db.create_proxied_path(session, username, sharing_name, fsp_name, path)
+                    new_path = db.create_proxied_path(session, username, sharing_name, fsp_name, path, url_prefix=url_prefix)
                     return _convert_proxied_path(new_path, settings.external_proxy_url)
                 except ValueError as e:
                     logger.error(f"Error creating proxied path: {e}")
@@ -970,12 +1012,10 @@ async def get_neuroglancer_short_links(request: Request,
         return NeuroglancerShortLinkResponse(links=links)
 
 
-    @app.get("/files/{sharing_key}/{sharing_name}")
-    @app.get("/files/{sharing_key}/{sharing_name}/{path:path}")
+    @app.get("/files/{sharing_key}/{path:path}")
     async def target_dispatcher(request: Request,
                                 sharing_key: str,
-                                sharing_name: str,
-                                path: str | None = '',
+                                path: str = '',
                                 list_type: Optional[int] = Query(None, alias="list-type"),
                                 continuation_token: Optional[str] = Query(None, alias="continuation-token"),
                                 delimiter: Optional[str] = Query(None, alias="delimiter"),
@@ -988,7 +1028,7 @@ async def target_dispatcher(request: Request,
         if 'acl' in request.query_params:
             return get_read_access_acl()
 
-        client, ctx = _get_file_proxy_client(sharing_key, sharing_name)
+        client, ctx, subpath = _get_file_proxy_client(sharing_key, path)
         if isinstance(client, Response):
             return client
 
@@ -1005,7 +1045,7 @@ async def target_dispatcher(request: Request,
             # Open file in user context, then immediately exit
             # The file descriptor retains access rights after we switch back to root
             with ctx:
-                handle = await client.open_object(path, range_header)
+                handle = await client.open_object(subpath, range_header)
 
             # Context exited! Now stream without holding the lock
             if isinstance(handle, ObjectHandle):
@@ -1015,14 +1055,14 @@ async def target_dispatcher(request: Request,
                 return handle
 
 
-    @app.head("/files/{sharing_key}/{sharing_name}/{path:path}")
-    async def head_object(sharing_key: str, sharing_name: str, path: str):
+    @app.head("/files/{sharing_key}/{path:path}")
+    async def head_object(sharing_key: str, path: str = ''):
         try:
-            client, ctx = _get_file_proxy_client(sharing_key, sharing_name)
+            client, ctx, subpath = _get_file_proxy_client(sharing_key, path)
             if isinstance(client, Response):
                 return client
             with ctx:
-                return await client.head_object(path)
+                return await client.head_object(subpath)
         except:
             logger.opt(exception=sys.exc_info()).info("Error requesting head")
             return get_error_response(500, "InternalError", "Error requesting HEAD", path)
diff --git a/frontend/src/__tests__/mocks/handlers.ts b/frontend/src/__tests__/mocks/handlers.ts
index e61b2d9b3..609be7049 100644
--- a/frontend/src/__tests__/mocks/handlers.ts
+++ b/frontend/src/__tests__/mocks/handlers.ts
@@ -18,16 +18,36 @@ export const handlers = [
     return HttpResponse.json({ paths: [] }, { status: 200 });
   }),
 
-  http.post('/api/proxied-path', () => {
+  http.post('/api/proxied-path', ({ request }) => {
+    const url = new URL(request.url);
+    const path = url.searchParams.get('path') || '/test/path';
+    const pathBasename = path.split('/').pop() || path;
+    const urlPrefix = url.searchParams.get('url_prefix') || pathBasename;
     return HttpResponse.json({
       username: 'testuser',
       sharing_key: 'testkey',
-      sharing_name: 'testshare',
+      sharing_name: pathBasename,
+      path: path,
+      fsp_name: url.searchParams.get('fsp_name') || 'test_fsp',
+      created_at: '2025-07-08T15:56:42.588942',
+      updated_at: '2025-07-08T15:56:42.588942',
+      url: 'http://127.0.0.1:7878/files/testkey/' + urlPrefix,
+      url_prefix: urlPrefix
+    });
+  }),
+
+  http.put('/api/proxied-path/:sharingKey', async ({ params, request }) => {
+    const { sharingKey } = params;
+    const body = (await request.json()) as { sharing_name?: string };
+    return HttpResponse.json({
+      username: 'testuser',
+      sharing_key: sharingKey,
+      sharing_name: body.sharing_name || 'testshare',
       path: '/test/path',
       fsp_name: 'test_fsp',
       created_at: '2025-07-08T15:56:42.588942',
       updated_at: '2025-07-08T15:56:42.588942',
-      url: 'http://127.0.0.1:7878/files/testkey/test/path'
+      url: 'http://127.0.0.1:7878/files/' + sharingKey + '/path'
     });
   }),
 
diff --git a/frontend/src/components/ui/Dialogs/DataLink.tsx b/frontend/src/components/ui/Dialogs/DataLink.tsx
index d11bbe27d..a09f17110 100644
--- a/frontend/src/components/ui/Dialogs/DataLink.tsx
+++ b/frontend/src/components/ui/Dialogs/DataLink.tsx
@@ -1,20 +1,27 @@
 /* eslint-disable react/destructuring-assignment */
 // Props are used for TypeScript type narrowing purposes and cannot be destructured at the beginning
 
-import { useState, SetStateAction } from 'react';
+import { useState, useMemo, SetStateAction } from 'react';
 import type { ReactNode, Dispatch } from 'react';
 import { Button, Typography } from '@material-tailwind/react';
+import { Link } from 'react-router';
 
 import type { ProxiedPath } from '@/contexts/ProxiedPathContext';
 import { useFileBrowserContext } from '@/contexts/FileBrowserContext';
+import { validateUrlPrefix } from '@/hooks/useDataToolLinks';
 import { usePreferencesContext } from '@/contexts/PreferencesContext';
 import { useZoneAndFspMapContext } from '@/contexts/ZonesAndFspMapContext';
-import { getPreferredPathForDisplay, makeMapKey } from '@/utils';
+import { makeMapKey } from '@/utils';
+import {
+  getPreferredPathForDisplay,
+  joinPaths,
+  normalizePosixStylePath
+} from '@/utils/pathHandling';
 import type { FileSharePath } from '@/shared.types';
 import type { PendingToolKey } from '@/hooks/useZarrMetadata';
 import FgDialog from './FgDialog';
 import TextWithFilePath from './TextWithFilePath';
-import AutomaticLinksToggle from '@/components/ui/PreferencesPage/DataLinkOptions';
+import DataLinkOptions from '@/components/ui/PreferencesPage/DataLinkOptions';
 import DeleteBtn from '@/components/ui/buttons/DeleteBtn';
 
 interface CommonDataLinkDialogProps {
@@ -25,7 +32,7 @@ interface CommonDataLinkDialogProps {
 interface CreateLinkFromToolsProps extends CommonDataLinkDialogProps {
   tools: true;
   action: 'create';
-  onConfirm: () => Promise<void>;
+  onConfirm: (urlPrefixOverride?: string) => Promise<void>;
   onCancel: () => void;
   setPendingToolKey: Dispatch<SetStateAction<PendingToolKey>>;
 }
@@ -33,7 +40,7 @@ interface CreateLinkFromToolsProps extends CommonDataLinkDialogProps {
 interface CreateLinkNotFromToolsProps extends CommonDataLinkDialogProps {
   tools: false;
   action: 'create';
-  onConfirm: () => Promise<void>;
+  onConfirm: (urlPrefixOverride?: string) => Promise<void>;
   onCancel: () => void;
 }
 
@@ -50,14 +57,17 @@ type DataLinkDialogProps =
   | DeleteLinkDialogProps;
 
 function CreateLinkBtn({
-  onConfirm
+  onConfirm,
+  disabled
 }: {
   readonly onConfirm: () => Promise<void>;
+  readonly disabled?: boolean;
 }) {
   return (
     <Button
       className="!rounded-md flex items-center gap-2"
       color="error"
+      disabled={disabled}
       onClick={async () => {
         await onConfirm();
       }}
@@ -105,22 +115,24 @@ function BtnContainer({ children }: { readonly children: ReactNode }) {
 
 export default function DataLinkDialog(props: DataLinkDialogProps) {
   const { fspName, filePath } = useFileBrowserContext();
-  const { pathPreference, areDataLinksAutomatic } = usePreferencesContext();
+  const { pathPreference, areDataLinksAutomatic, dataLinkSubpathMode } =
+    usePreferencesContext();
   const { zonesAndFspQuery } = useZoneAndFspMapContext();
   const [localAreDataLinksAutomatic] = useState(areDataLinksAutomatic);
 
+  const fspKey =
+    props.action === 'delete'
+      ? makeMapKey('fsp', props.proxiedPath.fsp_name)
+      : fspName
+        ? makeMapKey('fsp', fspName)
+        : '';
+
+  const pathFsp =
+    fspKey && zonesAndFspQuery.isSuccess
+      ? (zonesAndFspQuery.data[fspKey] as FileSharePath)
+      : null;
+
   function getDisplayPath(): string {
-    const fspKey =
-      props.action === 'delete'
-        ? makeMapKey('fsp', props.proxiedPath.fsp_name)
-        : fspName
-          ? makeMapKey('fsp', fspName)
-          : '';
-
-    const pathFsp =
-      fspKey && zonesAndFspQuery.isSuccess
-        ? (zonesAndFspQuery.data[fspKey] as FileSharePath)
-        : null;
     const targetPath =
       props.action === 'delete' ? props.proxiedPath.path : filePath;
 
@@ -130,6 +142,56 @@ export default function DataLinkDialog(props: DataLinkDialogProps) {
   }
   const displayPath = getDisplayPath();
 
+  // Generate preview components
+  const folderNameOnly = filePath ? filePath.split('/').pop() || filePath : '';
+  const linuxPath = pathFsp?.linux_path;
+  const transparentPath =
+    linuxPath && filePath
+      ? normalizePosixStylePath(joinPaths(linuxPath, filePath))
+      : filePath || '';
+
+  // Custom subpath local state (only used in this dialog, not persisted)
+  const [customSubpath, setCustomSubpath] = useState(folderNameOnly);
+
+  const customSubpathError = useMemo(
+    () =>
+      dataLinkSubpathMode === 'custom'
+        ? validateUrlPrefix(customSubpath)
+        : null,
+    [customSubpath, dataLinkSubpathMode]
+  );
+
+  // Compute preview based on current mode
+  function getPreviewPath(): string {
+    switch (dataLinkSubpathMode) {
+      case 'full_path':
+        return transparentPath;
+      case 'custom':
+        return customSubpath;
+      case 'name':
+      default:
+        return folderNameOnly;
+    }
+  }
+  const dataLinkPreview = `https://.../<key>/${getPreviewPath()}`;
+
+  // Whether this dialog was triggered by automatic+custom mode
+  const isAutoCustom =
+    props.action === 'create' &&
+    localAreDataLinksAutomatic &&
+    dataLinkSubpathMode === 'custom';
+
+  const handleConfirmWithPrefix = async () => {
+    if (props.action !== 'create') {
+      return;
+    }
+    if (dataLinkSubpathMode === 'custom') {
+      await props.onConfirm(customSubpath);
+    } else {
+      await props.onConfirm();
+    }
+  };
+
   return (
     <FgDialog
       onClose={() => {
@@ -140,29 +202,96 @@ export default function DataLinkDialog(props: DataLinkDialogProps) {
       }}
       open={props.showDataLinkDialog}
     >
-      <div className="flex flex-col gap-4 my-4">
-        {props.action === 'create' && localAreDataLinksAutomatic ? (
+      <div className="flex flex-col gap-2 my-4">
+        {props.action === 'create' && isAutoCustom ? (
+          <>
+            <Typography className="text-foreground font-semibold">
+              Set data link name
+            </Typography>
+            <Typography className="text-foreground">
+              Enter the name for your data link:
+            </Typography>
+            <input
+              className={`w-full p-2 rounded border bg-surface text-foreground font-mono text-sm ${customSubpathError ? 'border-error' : 'border-outline'}`}
+              onChange={e => setCustomSubpath(e.target.value)}
+              type="text"
+              value={customSubpath}
+            />
+            {customSubpathError ? (
+              <Typography className="text-error text-xs">
+                {customSubpathError}
+              </Typography>
+            ) : null}
+            <Typography className="text-foreground text-sm font-mono break-all bg-surface/30 p-2 rounded">
+              {dataLinkPreview}
+            </Typography>
+            <BtnContainer>
+              <CreateLinkBtn
+                disabled={!!customSubpathError}
+                onConfirm={handleConfirmWithPrefix}
+              />
+              <CancelBtn onCancel={props.onCancel} />
+            </BtnContainer>
+            <Typography className="text-xs text-foreground">
+              You're seeing this because you enabled custom data link naming in
+              your{' '}
+              <Link className="text-primary underline" to="/preferences">
+                preferences
+              </Link>
+              .
+            </Typography>
+          </>
+        ) : props.action === 'create' &&
+          localAreDataLinksAutomatic &&
+          dataLinkSubpathMode !== 'custom' ? (
           <> </>
         ) : props.action === 'create' && !localAreDataLinksAutomatic ? (
           <>
-            <TextWithFilePath
-              path={displayPath}
-              text="Are you sure you want to create a data link for this path?"
-            />
+            <Typography className="text-foreground font-semibold">
+              Are you sure you want to create a data link?
+            </Typography>
             <Typography className="text-foreground">
               If you share the data link with internal collaborators, they will
               be able to view these data.
             </Typography>
-            <div className="flex flex-col gap-2">
-              <Typography className="font-semibold text-foreground">
-                Don't ask me this again:
-              </Typography>
-              <AutomaticLinksToggle checkboxesOnly />
-            </div>
             <BtnContainer>
-              <CreateLinkBtn onConfirm={props.onConfirm} />
+              <CreateLinkBtn
+                disabled={!!customSubpathError}
+                onConfirm={handleConfirmWithPrefix}
+              />
               <CancelBtn onCancel={props.onCancel} />
             </BtnContainer>
+            <div className="flex flex-col gap-2 mt-4">
+              <Typography className="font-semibold text-foreground">
+                Data link settings:
+              </Typography>
+              <DataLinkOptions checkboxesOnly />
+              {dataLinkSubpathMode === 'custom' ? (
+                <>
+                  <input
+                    className={`w-full p-2 rounded border bg-surface text-foreground font-mono text-sm ${customSubpathError ? 'border-error' : 'border-outline'}`}
+                    onChange={e => setCustomSubpath(e.target.value)}
+                    type="text"
+                    value={customSubpath}
+                  />
+                  {customSubpathError ? (
+                    <Typography className="text-error text-xs">
+                      {customSubpathError}
+                    </Typography>
+                  ) : null}
+                </>
+              ) : null}
+              <Typography className="text-foreground text-sm font-mono break-all bg-surface/30 p-2 rounded">
+                {dataLinkPreview}
+              </Typography>
+              <Typography className="text-xs text-foreground">
+                You can always modify settings on the{' '}
+                <Link className="text-primary underline" to="/preferences">
+                  preferences page
+                </Link>{' '}
+                .
+              </Typography>
+            </div>
           </>
         ) : null}
         {props.action === 'delete' ? (
diff --git a/frontend/src/components/ui/PreferencesPage/DataLinkOptions.tsx b/frontend/src/components/ui/PreferencesPage/DataLinkOptions.tsx
index e8b25abc4..0ab835c34 100644
--- a/frontend/src/components/ui/PreferencesPage/DataLinkOptions.tsx
+++ b/frontend/src/components/ui/PreferencesPage/DataLinkOptions.tsx
@@ -1,41 +1,92 @@
 import toast from 'react-hot-toast';
+import { Typography } from '@material-tailwind/react';
 
 import { usePreferencesContext } from '@/contexts/PreferencesContext';
 import OptionsSection from '@/components/ui/PreferencesPage/OptionsSection';
 
-type AutomaticLinksToggleProps = {
+type DataLinkOptionsProps = {
   readonly checkboxesOnly?: boolean;
 };
 
-export default function AutomaticLinksToggle({
+const SUBPATH_MODES = [
+  { value: 'name' as const, label: 'Directory name only' },
+  { value: 'full_path' as const, label: 'Full path' },
+  { value: 'custom' as const, label: 'Custom' }
+];
+
+export default function DataLinkOptions({
   checkboxesOnly = false
-}: AutomaticLinksToggleProps) {
-  const { areDataLinksAutomatic, toggleAutomaticDataLinks } =
-    usePreferencesContext();
+}: DataLinkOptionsProps) {
+  const {
+    areDataLinksAutomatic,
+    toggleAutomaticDataLinks,
+    dataLinkSubpathMode,
+    setDataLinkSubpathMode
+  } = usePreferencesContext();
+
+  const automaticOption = {
+    checked: areDataLinksAutomatic,
+    id: 'automatic_data_links',
+    label: 'Enable automatic data link creation',
+    onChange: async () => {
+      const result = await toggleAutomaticDataLinks();
+      if (result.success) {
+        toast.success(
+          areDataLinksAutomatic
+            ? 'Disabled automatic data links'
+            : 'Enabled automatic data links'
+        );
+      } else {
+        toast.error(result.error);
+      }
+    }
+  };
+
+  const handleSubpathModeChange = async (
+    mode: 'name' | 'full_path' | 'custom'
+  ) => {
+    const result = await setDataLinkSubpathMode(mode);
+    if (result.success) {
+      const label = SUBPATH_MODES.find(m => m.value === mode)?.label;
+      toast.success(`Link name format set to: ${label}`);
+    } else {
+      toast.error(result.error);
+    }
+  };
 
   return (
-    <OptionsSection
-      checkboxesOnly={checkboxesOnly}
-      header="Data Links"
-      options={[
-        {
-          checked: areDataLinksAutomatic,
-          id: 'automatic_data_links',
-          label: 'Enable automatic data link creation',
-          onChange: async () => {
-            const result = await toggleAutomaticDataLinks();
-            if (result.success) {
-              toast.success(
-                areDataLinksAutomatic
-                  ? 'Disabled automatic data links'
-                  : 'Enabled automatic data links'
-              );
-            } else {
-              toast.error(result.error);
-            }
-          }
-        }
-      ]}
-    />
+    <>
+      <OptionsSection
+        checkboxesOnly={checkboxesOnly}
+        header="Data Links"
+        options={[automaticOption]}
+      />
+      <div className={checkboxesOnly ? '' : 'pl-4'}>
+        <Typography
+          className={`text-foreground ${checkboxesOnly ? '' : 'mt-2'} mb-1`}
+        >
+          Link name format:
+        </Typography>
+        {SUBPATH_MODES.map(mode => (
+          <div className="flex items-center gap-2" key={mode.value}>
+            <input
+              checked={dataLinkSubpathMode === mode.value}
+              className="icon-small accent-secondary-light dark:accent-secondary"
+              id={`subpath_mode_${mode.value}`}
+              name="subpath_mode"
+              onChange={() => handleSubpathModeChange(mode.value)}
+              type="radio"
+            />
+            <Typography
+              as="label"
+              className="text-foreground"
+              htmlFor={`subpath_mode_${mode.value}`}
+            >
+              {mode.label}
+            </Typography>
+          </div>
+        ))}
+      </div>
+    </>
   );
 }
diff --git a/frontend/src/components/ui/PropertiesDrawer/PropertiesDrawer.tsx b/frontend/src/components/ui/PropertiesDrawer/PropertiesDrawer.tsx
index 1bffce046..b94e9bae4 100644
--- a/frontend/src/components/ui/PropertiesDrawer/PropertiesDrawer.tsx
+++ b/frontend/src/components/ui/PropertiesDrawer/PropertiesDrawer.tsx
@@ -100,7 +100,8 @@ export default function PropertiesDrawer({
   const [activeTab, setActiveTab] = useState<string>('overview');
 
   const { fileQuery, fileBrowserState } = useFileBrowserContext();
-  const { pathPreference, areDataLinksAutomatic } = usePreferencesContext();
+  const { pathPreference, areDataLinksAutomatic, dataLinkSubpathMode } =
+    usePreferencesContext();
   const { ticketByPathQuery } = useTicketContext();
   const {
     allProxiedPathsQuery,
@@ -289,6 +290,7 @@ export default function PropertiesDrawer({
                       onChange={async () => {
                         if (
                           areDataLinksAutomatic &&
+                          dataLinkSubpathMode !== 'custom' &&
                           !proxiedPathByFspAndPathQuery.data
                         ) {
                           await handleCreateDataLink();
diff --git a/frontend/src/components/ui/Table/TableCard.tsx b/frontend/src/components/ui/Table/TableCard.tsx
index 659d9fc4a..f71a7eea0 100644
--- a/frontend/src/components/ui/Table/TableCard.tsx
+++ b/frontend/src/components/ui/Table/TableCard.tsx
@@ -164,15 +164,8 @@ const globalFilterFn: FilterFn<unknown> = (row, _columnId, filterValue) => {
 
   const query = String(filterValue).toLowerCase();
 
-  // Search all columns except the name column
-  // NOTE: this needs to change if we allow custom sharing names
-  // For now, the sharing name is always in the file path
+  // Search all columns
   const rowValues = row.getVisibleCells().flatMap(cell => {
-    // Exclude the name column (sharing_name)
-    if (cell.column.id === 'sharing_name') {
-      return [];
-    }
-
     const value = cell.getValue();
     if (value === null || value === undefined) {
       return [''];
diff --git a/frontend/src/components/ui/Table/linksColumns.tsx b/frontend/src/components/ui/Table/linksColumns.tsx
index c84725e30..90ecb5286 100644
--- a/frontend/src/components/ui/Table/linksColumns.tsx
+++ b/frontend/src/components/ui/Table/linksColumns.tsx
@@ -2,7 +2,6 @@ import { useState, useMemo } from 'react';
 import type { MouseEvent } from 'react';
 import { Typography } from '@material-tailwind/react';
 import type { ColumnDef } from '@tanstack/react-table';
-
 import DataLinkDialog from '@/components/ui/Dialogs/DataLink';
 import DataLinkUsageDialog from '@/components/ui/Dialogs/dataLinkUsage/DataLinkUsageDialog';
 import DataLinksActionsMenu from '@/components/ui/Menus/DataLinksActions';
@@ -58,6 +57,33 @@ function createPathMap(
   };
 }
 
+function NameCell({
+  item,
+  onContextMenu
+}: {
+  readonly item: ProxiedPath;
+  readonly onContextMenu?: (
+    e: MouseEvent<HTMLElement>,
+    data: { value: string }
+  ) => void;
+}) {
+  return (
+    <div
+      className="flex items-center truncate w-full h-full"
+      onContextMenu={e => {
+        e.preventDefault();
+        onContextMenu?.(e, { value: item.sharing_name });
+      }}
+    >
+      <FgTooltip label={item.sharing_name} triggerClasses={TRIGGER_CLASSES}>
+        <Typography className="text-foreground truncate select-all">
+          {item.sharing_name}
+        </Typography>
+      </FgTooltip>
+    </div>
+  );
+}
+
 function PathCell({
   displayPath,
   item,
@@ -206,28 +232,10 @@ export function useLinksColumns(): ColumnDef<ProxiedPath>[] {
       {
         accessorKey: 'sharing_name',
         header: 'Name',
-        cell: ({ cell, row, table }) => {
+        cell: ({ row, table }) => {
           const item = row.original;
           const onContextMenu = table.options.meta?.onCellContextMenu;
-          return (
-            <div
-              className="flex items-center truncate w-full h-full"
-              key={cell.id}
-              onContextMenu={e => {
-                e.preventDefault();
-                onContextMenu?.(e, { value: item.sharing_name });
-              }}
-            >
-              <FgTooltip
-                label={item.sharing_name}
-                triggerClasses={TRIGGER_CLASSES}
-              >
-                <Typography className="text-foreground truncate select-all">
-                  {item.sharing_name}
-                </Typography>
-              </FgTooltip>
-            </div>
-          );
+          return <NameCell item={item} onContextMenu={onContextMenu} />;
         },
         enableSorting: true
       },
diff --git a/frontend/src/contexts/PreferencesContext.tsx b/frontend/src/contexts/PreferencesContext.tsx
index e1c4e8d9f..1a3713ffb 100644
--- a/frontend/src/contexts/PreferencesContext.tsx
+++ b/frontend/src/contexts/PreferencesContext.tsx
@@ -48,6 +48,7 @@ type PreferencesContextType = {
   layout: string;
   hideDotFiles: boolean;
   areDataLinksAutomatic: boolean;
+  dataLinkSubpathMode: 'name' | 'full_path' | 'custom';
   disableNeuroglancerStateGeneration: boolean;
   disableHeuristicalLayerTypeDetection: boolean;
   useLegacyMultichannelApproach: boolean;
@@ -77,6 +78,9 @@ type PreferencesContextType = {
   setLayoutWithPropertiesOpen: () => Promise<Result<void>>;
   toggleHideDotFiles: () => Promise<Result<void>>;
   toggleAutomaticDataLinks: () => Promise<Result<void>>;
+  setDataLinkSubpathMode: (
+    mode: 'name' | 'full_path' | 'custom'
+  ) => Promise<Result<void>>;
   toggleDisableNeuroglancerStateGeneration: () => Promise<Result<void>>;
   toggleDisableHeuristicalLayerTypeDetection: () => Promise<Result<void>>;
   toggleUseLegacyMultichannelApproach: () => Promise<Result<void>>;
@@ -212,6 +216,20 @@ export const PreferencesProvider = ({
     );
   };
 
+  const setDataLinkSubpathMode = async (
+    mode: 'name' | 'full_path' | 'custom'
+  ): Promise<Result<void>> => {
+    try {
+      await updatePreferenceMutation.mutateAsync({
+        key: 'dataLinkSubpathMode',
+        value: mode
+      });
+      return createSuccess(undefined);
+    } catch (error) {
+      return handleError(error);
+    }
+  };
+
   const toggleDisableNeuroglancerStateGeneration = async (): Promise<
     Result<void>
   > => {
@@ -524,6 +542,7 @@ export const PreferencesProvider = ({
     hideDotFiles: preferencesQuery.data?.hideDotFiles || false,
     areDataLinksAutomatic:
       preferencesQuery.data?.areDataLinksAutomatic ?? false,
+    dataLinkSubpathMode: preferencesQuery.data?.dataLinkSubpathMode ?? 'name',
     disableNeuroglancerStateGeneration:
       preferencesQuery.data?.disableNeuroglancerStateGeneration || false,
     disableHeuristicalLayerTypeDetection:
@@ -555,6 +574,7 @@ export const PreferencesProvider = ({
     setLayoutWithPropertiesOpen,
     toggleHideDotFiles,
     toggleAutomaticDataLinks,
+    setDataLinkSubpathMode,
     toggleDisableNeuroglancerStateGeneration,
     toggleDisableHeuristicalLayerTypeDetection,
     toggleUseLegacyMultichannelApproach,
diff --git a/frontend/src/contexts/ProxiedPathContext.tsx b/frontend/src/contexts/ProxiedPathContext.tsx
index 5d964540d..3697b68e4 100644
--- a/frontend/src/contexts/ProxiedPathContext.tsx
+++ b/frontend/src/contexts/ProxiedPathContext.tsx
@@ -18,6 +18,7 @@ export type ProxiedPath = {
   created_at: string;
   updated_at: string;
   url: string;
+  url_prefix: string;
 };
 
 type ProxiedPathContextType = {
diff --git a/frontend/src/hooks/useDataToolLinks.ts b/frontend/src/hooks/useDataToolLinks.ts
index f882c69b4..50fcec5b3 100644
--- a/frontend/src/hooks/useDataToolLinks.ts
+++ b/frontend/src/hooks/useDataToolLinks.ts
@@ -9,9 +9,35 @@ import {
 import { usePreferencesContext } from '@/contexts/PreferencesContext';
 import { useExternalBucketContext } from '@/contexts/ExternalBucketContext';
 import { useFileBrowserContext } from '@/contexts/FileBrowserContext';
+import {
+  escapePathForUrl,
+  joinPaths,
+  normalizePosixStylePath
+} from '@/utils/pathHandling';
 import useCopyTooltip from './useCopyTooltip';
 import type { OpenWithToolUrls, PendingToolKey } from '@/hooks/useZarrMetadata';
 
+const VALID_URL_PREFIX_RE = /^[A-Za-z0-9\-._~/!@$&'()*+,;:=%]+$/;
+
+export function validateUrlPrefix(value: string): string | null {
+  if (!value || !value.trim()) {
+    return 'Data link name must not be empty';
+  }
+  if (!VALID_URL_PREFIX_RE.test(value)) {
+    const invalidChars = [
+      ...new Set([...value].filter(c => !VALID_URL_PREFIX_RE.test(c)))
+    ];
+    return `Contains invalid URL characters: ${invalidChars.join(' ')}`;
+  }
+  if (value.startsWith('/') || value.endsWith('/')) {
+    return 'Data link name must not start or end with /';
+  }
+  if (value.includes('//')) {
+    return 'Data link name must not contain consecutive slashes';
+  }
+  return null;
+}
+
 // Overload for ZarrPreview usage with required parameters
 export default function useDataToolLinks(
   setShowDataLinkDialog: Dispatch<SetStateAction<boolean>>,
@@ -22,7 +48,7 @@ export default function useDataToolLinks(
   handleCreateDataLink: (pathOverride?: string) => Promise<boolean>;
   handleDeleteDataLink: (proxiedPath: ProxiedPath) => Promise<void>;
   handleToolClick: (toolKey: PendingToolKey) => Promise<void>;
-  handleDialogConfirm: () => Promise<void>;
+  handleDialogConfirm: (urlPrefixOverride?: string) => Promise<void>;
   handleDialogCancel: () => void;
   showCopiedTooltip: boolean;
 };
@@ -34,7 +60,7 @@ export default function useDataToolLinks(
   handleCreateDataLink: (pathOverride?: string) => Promise<boolean>;
   handleDeleteDataLink: (proxiedPath: ProxiedPath) => Promise<void>;
   handleToolClick: (toolKey: PendingToolKey) => Promise<void>;
-  handleDialogConfirm: () => Promise<void>;
+  handleDialogConfirm: (urlPrefixOverride?: string) => Promise<void>;
   handleDialogCancel: () => void;
   showCopiedTooltip: boolean;
 };
@@ -57,12 +83,14 @@ export default function useDataToolLinks(
     currentDirProxiedPathQuery
   } = useProxiedPathContext();
 
-  const { areDataLinksAutomatic } = usePreferencesContext();
+  const { areDataLinksAutomatic, dataLinkSubpathMode } =
+    usePreferencesContext();
   const { externalDataUrlQuery } = useExternalBucketContext();
   const { handleCopy, showCopiedTooltip } = useCopyTooltip();
 
   const handleCreateDataLink = async (
-    pathOverride?: string
+    pathOverride?: string,
+    urlPrefixOverride?: string
   ): Promise<boolean> => {
     const path = pathOverride || fileBrowserState.dataLinkPath;
     if (!fileQuery.data?.currentFileSharePath) {
@@ -75,9 +103,39 @@ export default function useDataToolLinks(
     }
 
     try {
+      let urlPrefix: string;
+      if (urlPrefixOverride !== undefined) {
+        urlPrefix = urlPrefixOverride;
+      } else {
+        const linuxPath = fileQuery.data.currentFileSharePath.linux_path;
+        switch (dataLinkSubpathMode) {
+          case 'full_path':
+            urlPrefix = escapePathForUrl(
+              normalizePosixStylePath(
+                linuxPath ? joinPaths(linuxPath, path) : path
+              )
+            );
+            break;
+          case 'custom':
+            urlPrefix = path.split('/').pop() || path;
+            break;
+          case 'name':
+          default:
+            urlPrefix = escapePathForUrl(path.split('/').pop() || path);
+            break;
+        }
+      }
+
+      const validationError = validateUrlPrefix(urlPrefix);
+      if (validationError) {
+        toast.error(validationError);
+        return false;
+      }
+
       await createProxiedPathMutation.mutateAsync({
         fsp_name: fileQuery.data.currentFileSharePath.name,
-        path
+        path,
+        url_prefix: urlPrefix
       });
       toast.success('Data link created successfully');
       await allProxiedPathsQuery.refetch();
@@ -172,7 +230,7 @@ export default function useDataToolLinks(
 
   const handleToolClick = async (toolKey: PendingToolKey) => {
     if (!currentDirProxiedPathQuery.data && !externalDataUrlQuery.data) {
-      if (areDataLinksAutomatic) {
+      if (areDataLinksAutomatic && dataLinkSubpathMode !== 'custom') {
         await createLinkAndExecuteAction(toolKey);
       } else {
         setPendingToolKey?.(toolKey);
@@ -188,11 +246,32 @@ export default function useDataToolLinks(
 
   // First case is for link creation through a data tool button click
   // Second case is for link creation through the PropertiesDrawer dialog
-  const handleDialogConfirm = async () => {
+  const handleDialogConfirm = async (urlPrefixOverride?: string) => {
     if (pendingToolKey) {
-      await createLinkAndExecuteAction();
+      if (urlPrefixOverride !== undefined) {
+        const success = await handleCreateDataLink(
+          fileQuery.data?.currentFileOrFolder?.path,
+          urlPrefixOverride
+        );
+        if (success) {
+          // Wait for URLs to update then execute tool action
+          let attempts = 0;
+          const maxAttempts = 50;
+          while (attempts < maxAttempts) {
+            const currentUrls = currentUrlsRef.current;
+            if (currentUrls && currentUrls.copy && currentUrls.copy !== '') {
+              await executeToolAction(pendingToolKey, currentUrls);
+              break;
+            }
+            await new Promise(resolve => setTimeout(resolve, 100));
+            attempts++;
+          }
+        }
+      } else {
+        await createLinkAndExecuteAction();
+      }
     } else {
-      await handleCreateDataLink();
+      await handleCreateDataLink(undefined, urlPrefixOverride);
     }
     setShowDataLinkDialog?.(false);
   };
diff --git a/frontend/src/queries/preferencesQueries.ts b/frontend/src/queries/preferencesQueries.ts
index 57f508151..b9b357982 100644
--- a/frontend/src/queries/preferencesQueries.ts
+++ b/frontend/src/queries/preferencesQueries.ts
@@ -33,6 +33,7 @@ type PreferencesApiResponse = {
   layout?: { value: string };
   hideDotFiles?: { value: boolean };
   areDataLinksAutomatic?: { value: boolean };
+  dataLinkSubpathMode?: { value: string };
   disableNeuroglancerStateGeneration?: { value: boolean };
   disableHeuristicalLayerTypeDetection?: { value: boolean };
   useLegacyMultichannelApproach?: { value: boolean };
@@ -65,6 +66,7 @@ export type PreferencesQueryData = {
   layout: string;
   hideDotFiles: boolean;
   areDataLinksAutomatic: boolean;
+  dataLinkSubpathMode: 'name' | 'full_path' | 'custom';
   disableNeuroglancerStateGeneration: boolean;
   disableHeuristicalLayerTypeDetection: boolean;
   useLegacyMultichannelApproach: boolean;
@@ -229,6 +231,11 @@ const createTransformPreferences = (
       layout: rawData.layout?.value || '',
       hideDotFiles: rawData.hideDotFiles?.value || false,
       areDataLinksAutomatic: rawData.areDataLinksAutomatic?.value ?? false,
+      dataLinkSubpathMode:
+        (rawData.dataLinkSubpathMode?.value as
+          | 'name'
+          | 'full_path'
+          | 'custom') ?? 'name',
       disableNeuroglancerStateGeneration:
         rawData.disableNeuroglancerStateGeneration?.value || false,
       disableHeuristicalLayerTypeDetection:
diff --git a/frontend/src/queries/proxiedPathQueries.ts b/frontend/src/queries/proxiedPathQueries.ts
index 315aa8208..604ed1e50 100644
--- a/frontend/src/queries/proxiedPathQueries.ts
+++ b/frontend/src/queries/proxiedPathQueries.ts
@@ -27,6 +27,7 @@ type ProxiedPathApiResponse = {
 type CreateProxiedPathPayload = {
   fsp_name: string;
   path: string;
+  url_prefix?: string;
 };
 
 /**
@@ -178,10 +179,14 @@ export function useCreateProxiedPathMutation(): UseMutationResult<
 
   return useMutation({
     mutationFn: async (payload: CreateProxiedPathPayload) => {
-      const url = buildUrl('/api/proxied-path', null, {
+      const queryParams: Record<string, string> = {
         fsp_name: payload.fsp_name,
         path: payload.path
-      });
+      };
+      if (payload.url_prefix !== undefined) {
+        queryParams.url_prefix = payload.url_prefix;
+      }
+      const url = buildUrl('/api/proxied-path', null, queryParams);
       const proxiedPath = await sendRequestAndThrowForNotOk(url, 'POST');
       return proxiedPath as ProxiedPath;
     },
diff --git a/tests/test_endpoints.py b/tests/test_endpoints.py
index 96be209df..11f4c5bfd 100644
--- a/tests/test_endpoints.py
+++ b/tests/test_endpoints.py
@@ -1246,6 +1246,158 @@ def test_head_content_with_symlink(test_client, temp_dir):
     assert int(response.headers["Content-Length"]) == len(target_content)
 
 
+def test_create_non_transparent_proxied_path(test_client, temp_dir):
+    """Test creating a non-transparent link uses basename in URL"""
+    path = "test_proxied_path"
+
+    response = test_client.post(f"/api/proxied-path?fsp_name=tempdir&path={path}")
+    assert response.status_code == 200
+    data = response.json()
+    # URL should use basename (last path component)
+    assert data["url"].endswith(f"/{data['sharing_key']}/test_proxied_path")
+
+
+def test_create_proxied_path_with_custom_url_prefix(test_client, temp_dir):
+    """Test creating a link with a custom url_prefix"""
+    # Create nested dirs for a multi-segment path
+    nested_path = os.path.join(temp_dir, "a", "b", "c")
+    os.makedirs(nested_path, exist_ok=True)
+    path = "a/b/c"
+
+    response = test_client.post(f"/api/proxied-path?fsp_name=tempdir&path={path}&url_prefix=custom/prefix")
+    assert response.status_code == 200
+    data = response.json()
+    # URL should use the custom url_prefix
+    assert data["url"].endswith(f"/{data['sharing_key']}/custom/prefix")
+    assert data["url_prefix"] == "custom/prefix"
+
+
+def test_proxy_resolve_non_transparent(test_client, temp_dir):
+    """Test that a non-transparent link resolves correctly via basename prefix match"""
+    # Create a file inside the proxied directory
+    proxied_dir = os.path.join(temp_dir, "test_proxied_path")
+    test_file = os.path.join(proxied_dir, "data.txt")
+    with open(test_file, "w") as f:
+        f.write("hello")
+
+    # Create the non-transparent link
+    response = test_client.post(f"/api/proxied-path?fsp_name=tempdir&path=test_proxied_path")
+    assert response.status_code == 200
+    sharing_key = response.json()["sharing_key"]
+
+    # Access through the proxy using basename prefix
+    response = test_client.get(f"/files/{sharing_key}/test_proxied_path/data.txt")
+    assert response.status_code == 200
+    assert response.text == "hello"
+
+
+def test_proxy_resolve_custom_url_prefix(test_client, temp_dir):
+    """Test that a link with custom url_prefix resolves correctly"""
+    nested_dir = os.path.join(temp_dir, "a", "b")
+    os.makedirs(nested_dir, exist_ok=True)
+    test_file = os.path.join(nested_dir, "data.txt")
+    with open(test_file, "w") as f:
+        f.write("custom prefix hello")
+
+    response = test_client.post(f"/api/proxied-path?fsp_name=tempdir&path=a/b&url_prefix=my/custom/prefix")
+    assert response.status_code == 200
+    sharing_key = response.json()["sharing_key"]
+
+    # Access through the proxy using the custom url_prefix
+    response = test_client.get(f"/files/{sharing_key}/my/custom/prefix/data.txt")
+    assert response.status_code == 200
+    assert response.text == "custom prefix hello"
+
+
+def test_proxy_path_boundary_guard(test_client, temp_dir):
+    """Test that prefix 'foo' does NOT match 'foobar/file' (path boundary enforcement)"""
+    # Create two directories: "foo" and "foobar"
+    foo_dir = os.path.join(temp_dir, "foo")
+    foobar_dir = os.path.join(temp_dir, "foobar")
+    os.makedirs(foo_dir, exist_ok=True)
+    os.makedirs(foobar_dir, exist_ok=True)
+    with open(os.path.join(foobar_dir, "secret.txt"), "w") as f:
+        f.write("secret")
+
+    # Create a non-transparent link for "foo"
+    response = test_client.post(f"/api/proxied-path?fsp_name=tempdir&path=foo")
+    assert response.status_code == 200
+    sharing_key = response.json()["sharing_key"]
+
+    # Try to access "foobar/secret.txt" via the "foo" sharing key - should fail
+    response = test_client.get(f"/files/{sharing_key}/foobar/secret.txt")
+    assert response.status_code == 404
+
+
+def test_proxy_resolve_url_encoded_path_non_transparent(test_client, temp_dir):
+    """Test that a non-transparent link resolves when the basename contains URL-encoded characters"""
+    dir_name = "my data set"
+    proxied_dir = os.path.join(temp_dir, dir_name)
+    os.makedirs(proxied_dir, exist_ok=True)
+    with open(os.path.join(proxied_dir, "file.txt"), "w") as f:
+        f.write("encoded hello")
+
+    response = test_client.post(f"/api/proxied-path?fsp_name=tempdir&path={dir_name}")
+    assert response.status_code == 200
+    sharing_key = response.json()["sharing_key"]
+
+    # Request with URL-encoded space (%20) in the basename
+    response = test_client.get(f"/files/{sharing_key}/my%20data%20set/file.txt")
+    assert response.status_code == 200
+    assert response.text == "encoded hello"
+
+
+def test_proxy_resolve_url_encoded_path_custom_prefix(test_client, temp_dir):
+    """Test that a link with URL-encoded characters in url_prefix resolves correctly"""
+    nested_dir = os.path.join(temp_dir, "my folder", "sub dir")
+    os.makedirs(nested_dir, exist_ok=True)
+    with open(os.path.join(nested_dir, "file.txt"), "w") as f:
+        f.write("encoded custom prefix hello")
+
+    response = test_client.post(f"/api/proxied-path?fsp_name=tempdir&path=my folder/sub dir&url_prefix=my folder/sub dir")
+    assert response.status_code == 200
+    sharing_key = response.json()["sharing_key"]
+
+    # Request with URL-encoded spaces in the url_prefix
+    response = test_client.get(f"/files/{sharing_key}/my%20folder/sub%20dir/file.txt")
+    assert response.status_code == 200
+    assert response.text == "encoded custom prefix hello"
+
+
+def test_proxy_resolve_special_characters_in_path(test_client, temp_dir):
+    """Test that paths with special characters (parentheses, brackets, etc.) resolve correctly"""
+    dir_name = "experiment (2) [final]"
+    proxied_dir = os.path.join(temp_dir, dir_name)
+    os.makedirs(proxied_dir, exist_ok=True)
+    with open(os.path.join(proxied_dir, "result.txt"), "w") as f:
+        f.write("special chars")
+
+    response = test_client.post(f"/api/proxied-path?fsp_name=tempdir&path={dir_name}")
+    assert response.status_code == 200
+    sharing_key = response.json()["sharing_key"]
+
+    response = test_client.get(f"/files/{sharing_key}/experiment%20%282%29%20%5Bfinal%5D/result.txt")
+    assert response.status_code == 200
+    assert response.text == "special chars"
+
+
+def test_proxy_reject_mismatched_url_prefix(test_client, temp_dir):
+    """Test that a link rejects requests with a different prefix than url_prefix"""
+    nested_dir = os.path.join(temp_dir, "a", "b")
+    os.makedirs(nested_dir, exist_ok=True)
+    with open(os.path.join(nested_dir, "file.txt"), "w") as f:
+        f.write("should not be accessible")
+
+    # Create link for "a/b" with default url_prefix (basename "b")
+    response = test_client.post(f"/api/proxied-path?fsp_name=tempdir&path=a/b")
+    assert response.status_code == 200
+    sharing_key = response.json()["sharing_key"]
+
+    # Attempt to access via full path "a/b" — should be rejected since url_prefix is just "b"
+    response = test_client.get(f"/files/{sharing_key}/a/b/file.txt")
+    assert response.status_code == 404
+
+
 def test_broken_symlink_in_file_listing(test_client, temp_dir):
     """Test that broken symlinks appear in /api/files response with correct properties"""
     # Create a broken symlink pointing to a nonexistent path