diff --git a/.changeset/drift-multi-parameter-path-segments.md b/.changeset/drift-multi-parameter-path-segments.md
new file mode 100644
index 0000000000..fed5547851
--- /dev/null
+++ b/.changeset/drift-multi-parameter-path-segments.md
@@ -0,0 +1,7 @@
+---
+'@redocly/cli': patch
+---
+
+Fixed `drift` and `coverage` failing to match a path template whose segment mixes literal text with parameters, such as `/instances/{worldId}:{instanceId}`.
+Only a segment that was entirely one parameter was recognized, so these templates were compiled as literal text and never matched any request.
+Affected requests were reported as undocumented by `drift` and left out of the `coverage` figures.
diff --git a/packages/cli/src/commands/drift/__tests__/compile-openapi-path.test.ts b/packages/cli/src/commands/drift/__tests__/compile-openapi-path.test.ts
new file mode 100644
index 0000000000..f7e83d2039
--- /dev/null
+++ b/packages/cli/src/commands/drift/__tests__/compile-openapi-path.test.ts
@@ -0,0 +1,58 @@
+import { compileOpenApiPath } from '../utils/http.js';
+
+describe('compileOpenApiPath', () => {
+  it('compiles a segment that is a single parameter', () => {
+    const { regex, params } = compileOpenApiPath('/users/{userId}');
+
+    expect(params).toEqual(['userId']);
+    expect(regex.exec('/users/usr_abc')?.[1]).toBe('usr_abc');
+  });
+
+  it('does not let a parameter span a path separator', () => {
+    const { regex } = compileOpenApiPath('/users/{userId}');
+
+    expect(regex.exec('/users/usr_abc/friends')).toBeNull();
+  });
+
+  it('compiles two parameters separated by a literal inside one segment', () => {
+    const { regex, params } = compileOpenApiPath('/instances/{worldId}:{instanceId}');
+
+    expect(params).toEqual(['worldId', 'instanceId']);
+
+    const match = regex.exec(
+      '/instances/wrld_a:85981~group(grp_b)~groupAccessType(public)~region(us)'
+    );
+    expect(match?.[1]).toBe('wrld_a');
+    expect(match?.[2]).toBe('85981~group(grp_b)~groupAccessType(public)~region(us)');
+  });
+
+  it('splits on the first separator when the trailing value holds another', () => {
+    const { regex } = compileOpenApiPath('/instances/{worldId}:{instanceId}');
+    const match = regex.exec('/instances/wrld_a:12345~region(us):extra');
+
+    expect(match?.[1]).toBe('wrld_a');
+    expect(match?.[2]).toBe('12345~region(us):extra');
+  });
+
+  it('keeps matching a multi-parameter segment when a suffix segment follows', () => {
+    const { regex } = compileOpenApiPath('/instances/{worldId}:{instanceId}/shortName');
+
+    expect(regex.exec('/instances/wrld_a:123~private(usr_b)/shortName')?.[2]).toBe(
+      '123~private(usr_b)'
+    );
+  });
+
+  it('ranks a partially literal segment above a bare parameter', () => {
+    expect(compileOpenApiPath('/instances/{worldId}:{instanceId}').score).toBeGreaterThan(
+      compileOpenApiPath('/instances/{instanceId}').score
+    );
+  });
+
+  it('treats a segment with no parameters as a literal', () => {
+    const { regex, params } = compileOpenApiPath('/instances/recent');
+
+    expect(params).toEqual([]);
+    expect(regex.exec('/instances/anything')).toBeNull();
+    expect(regex.exec('/instances/recent')).not.toBeNull();
+  });
+});
diff --git a/packages/cli/src/commands/drift/utils/http.ts b/packages/cli/src/commands/drift/utils/http.ts
index 5e2f4a9397..cee38562b9 100644
--- a/packages/cli/src/commands/drift/utils/http.ts
+++ b/packages/cli/src/commands/drift/utils/http.ts
@@ -167,14 +167,36 @@ export function compileOpenApiPath(pathTemplate: string): {
         return '';
       }
 
-      const paramMatch = segment.match(/^\{([^}]+)\}$/);
-      if (paramMatch) {
+      // A segment may hold several parameters around literal text, as in
+      // `/instances/{worldId}:{instanceId}`. Matching the whole segment as one
+      // parameter would miss those, and treating it as a literal never matches.
+      const paramsBefore = params.length;
+      let compiled = '';
+      let literalLength = 0;
+      let offset = 0;
+
+      for (const paramMatch of segment.matchAll(/\{([^}]+)\}/g)) {
+        const literal = segment.slice(offset, paramMatch.index);
+
+        compiled += escapeRegex(literal);
+        literalLength += literal.length;
         params.push(paramMatch[1]);
-        return '([^/]+)';
+        compiled += '([^/]+?)';
+        offset = paramMatch.index + paramMatch[0].length;
       }
 
-      score += 2;
-      return escapeRegex(segment);
+      const trailing = segment.slice(offset);
+      compiled += escapeRegex(trailing);
+      literalLength += trailing.length;
+
+      if (params.length === paramsBefore) {
+        score += 2;
+      } else if (literalLength > 0) {
+        // More specific than a bare parameter, less so than a whole literal.
+        score += 1;
+      }
+
+      return compiled;
     })
     .join('/');