diff --git a/CHANGELOG.md b/CHANGELOG.md
index 84beae193..b6a682f50 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -9,6 +9,7 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
 
 ### Fixed
 - Fixed search query parser rejecting parenthesized regex alternation in filter values (e.g. `file:(test|spec)`, `-file:(test|spec)`). [#946](https://github.com/sourcebot-dev/sourcebot/pull/946)
+- Fixed `content:` filter ignoring the regex toggle. [#947](https://github.com/sourcebot-dev/sourcebot/pull/947)
 
 ## [4.12.0] - 2026-02-26
 
diff --git a/packages/web/src/features/search/parser.ts b/packages/web/src/features/search/parser.ts
index 753e1252e..b0e1e09af 100644
--- a/packages/web/src/features/search/parser.ts
+++ b/packages/web/src/features/search/parser.ts
@@ -272,7 +272,15 @@ const transformTreeToIR = async ({
                 };
 
             case ContentExpr:
-                return {
+                return isRegexEnabled ? {
+                    regexp: {
+                        regexp: value,
+                        case_sensitive: isCaseSensitivityEnabled,
+                        file_name: false,
+                        content: true
+                    },
+                    query: "regexp"
+                } : {
                     substring: {
                         pattern: value,
                         case_sensitive: isCaseSensitivityEnabled,