diff --git a/server/src/queries/asset.repository.sql b/server/src/queries/asset.repository.sql
index b790705cc..dbdae444d 100644
--- a/server/src/queries/asset.repository.sql
+++ b/server/src/queries/asset.repository.sql
@@ -531,7 +531,7 @@ where
   and "libraryId" = $5::uuid
   and (
     not "originalPath" like $6
-    or "originalPath" like $7
+    or "originalPath" ~ $7
   )
 
 -- AssetRepository.filterNewExternalAssetPaths
diff --git a/server/src/repositories/asset.repository.ts b/server/src/repositories/asset.repository.ts
index 9427bfca6..189c5c621 100644
--- a/server/src/repositories/asset.repository.ts
+++ b/server/src/repositories/asset.repository.ts
@@ -54,7 +54,7 @@ import {
   withTagId,
   withTags,
 } from 'src/utils/database';
-import { globToSqlPattern } from 'src/utils/misc';
+import { globToPostgresRegex } from 'src/utils/misc';
 
 export type AssetStats = Record<AssetType, number>;
 
@@ -1086,7 +1086,7 @@ export class AssetRepository {
     exclusionPatterns: string[],
   ): Promise<UpdateResult> {
     const paths = importPaths.map((importPath) => `${importPath}%`);
-    const exclusions = exclusionPatterns.map((pattern) => globToSqlPattern(pattern));
+    const exclusions = exclusionPatterns.map((pattern) => globToPostgresRegex(pattern));
 
     return this.db
       .updateTable('asset')
@@ -1100,7 +1100,7 @@ export class AssetRepository {
       .where((eb) =>
         eb.or([
           eb.not(eb.or(paths.map((path) => eb('originalPath', 'like', path)))),
-          eb.or(exclusions.map((path) => eb('originalPath', 'like', path))),
+          eb.or(exclusions.map((pattern) => eb('originalPath', '~', pattern))),
         ]),
       )
       .executeTakeFirstOrThrow();
diff --git a/server/src/utils/misc.spec.ts b/server/src/utils/misc.spec.ts
index 3c4548293..e6b36d4a0 100644
--- a/server/src/utils/misc.spec.ts
+++ b/server/src/utils/misc.spec.ts
@@ -1,4 +1,4 @@
-import { getKeysDeep, globToSqlPattern, unsetDeep } from 'src/utils/misc';
+import { getKeysDeep, globToPostgresRegex, unsetDeep } from 'src/utils/misc';
 import { describe, expect, it } from 'vitest';
 
 describe('getKeysDeep', () => {
@@ -52,18 +52,26 @@ describe('unsetDeep', () => {
   });
 });
 
-describe('globToSqlPattern', () => {
-  const testCases = [
-    ['**/Raw/**', '%/Raw/%'],
-    ['**/abc/*.tif', '%/abc/%.tif'],
-    ['**/*.tif', '%/%.tif'],
-    ['**/*.jp?', '%/%.jp_'],
-    ['**/@eaDir/**', '%/@eaDir/%'],
-    ['**/._*', `%/._%`],
-    ['/absolute/path/**', `/absolute/path/%`],
+const matches = (glob: string, value: string) => new RegExp(globToPostgresRegex(glob)).test(value);
+
+describe('globToPostgresRegex', () => {
+  const testCases: [string, string, boolean][] = [
+    ['**/Raw/**', '/foo/Raw/bar.jpg', true],
+    ['**/Raw/**', '/foo/bar.jpg', false],
+    ['**/abc/*.tif', '/foo/abc/scan.tif', true],
+    ['**/abc/*.tif', '/foo/abc/sub/scan.tif', false],
+    ['**/*.tif', '/foo/bar.tif', true],
+    ['**/*.jp?', '/foo/bar.jpg', true],
+    ['**/@eaDir/**', '/foo/@eaDir/thumb.jpg', true],
+    ['**/._*', '/foo/._resource', true],
+    ['/absolute/path/**', '/absolute/path/photo.jpg', true],
+    ['/absolute/path/**', '/other/path/photo.jpg', false],
+    // a bare `*` must not cross a path separator, unlike SQL `LIKE`'s `%`
+    ['/path/*.*', '/path/photo.jpg', true],
+    ['/path/*.*', '/path/2020/photo.jpg', false],
   ];
 
-  it.each(testCases)('should convert %s to %s', (input, expected) => {
-    expect(globToSqlPattern(input)).toEqual(expected);
+  it.each(testCases)('should match %s against %s as %s', (glob, value, expected) => {
+    expect(matches(glob, value)).toEqual(expected);
   });
 });
diff --git a/server/src/utils/misc.ts b/server/src/utils/misc.ts
index 84ebc7e98..7727a8eb8 100644
--- a/server/src/utils/misc.ts
+++ b/server/src/utils/misc.ts
@@ -12,7 +12,6 @@ import { cleanupOpenApiDoc } from 'nestjs-zod';
 import { writeFileSync } from 'node:fs';
 import path from 'node:path';
 import picomatch from 'picomatch';
-import parse from 'picomatch/lib/parse';
 import { CLIP_MODEL_INFO, JOBS_ASSET_PAGINATION_SIZE, endpointTags, serverVersion } from 'src/constants';
 import { extraModels } from 'src/decorators';
 import { SystemConfig } from 'src/dtos/config.dto';
@@ -338,37 +337,10 @@ export const useSwagger = (app: INestApplication, { write }: { write: boolean })
   }
 };
 
-const convertTokenToSqlPattern = (token: parse.Token): string => {
-  switch (token.type) {
-    case 'slash': {
-      return '/';
-    }
-    case 'text': {
-      return token.value;
-    }
-    case 'globstar':
-    case 'star': {
-      return '%';
-    }
-    case 'underscore': {
-      return String.raw`\_`;
-    }
-    case 'qmark': {
-      return '_';
-    }
-    case 'dot': {
-      return '.';
-    }
-    default: {
-      return '';
-    }
-  }
-};
-
-export const globToSqlPattern = (glob: string) => {
-  const tokens = picomatch.parse(glob).tokens;
-  return tokens.map((token) => convertTokenToSqlPattern(token)).join('');
-};
+// Compiles a glob to the equivalent Postgres regex (Postgres's Advanced Regular Expression
+// dialect is a superset of what picomatch emits, so the two stay in sync with `picomatch.isMatch`,
+// including which paths a lone `*` may cross vs `/`).
+export const globToPostgresRegex = (glob: string) => picomatch.makeRe(glob).source;
 
 export function clamp(value: number, min: number, max: number) {
   return Math.max(min, Math.min(max, value));