diff --git a/apps/yaak-client/components/HttpRequestPane.tsx b/apps/yaak-client/components/HttpRequestPane.tsx
index c5688a620..89d3bd7f3 100644
--- a/apps/yaak-client/components/HttpRequestPane.tsx
+++ b/apps/yaak-client/components/HttpRequestPane.tsx
@@ -19,6 +19,7 @@ import { useSendAnyHttpRequest } from "../hooks/useSendAnyHttpRequest";
 import { deepEqualAtom } from "../lib/atoms";
 import { languageFromContentType } from "../lib/contentType";
 import { generateId } from "../lib/generateId";
+import { extractPathPlaceholders } from "../lib/pathPlaceholders";
 import {
   BODY_TYPE_BINARY,
   BODY_TYPE_FORM_MULTIPART,
@@ -131,9 +132,7 @@ export function HttpRequestPane({ style, fullHeight, className, activeRequest }:
   );
 
   const { urlParameterPairs, urlParametersKey } = useMemo(() => {
-    const placeholderNames = Array.from(activeRequest.url.matchAll(/\/(:[^/]+)/g)).map(
-      (m) => m[1] ?? "",
-    );
+    const placeholderNames = extractPathPlaceholders(activeRequest.url);
     const nonEmptyParameters = activeRequest.urlParameters.filter((p) => p.name || p.value);
     const items: Pair[] = [...nonEmptyParameters];
     for (const name of placeholderNames) {
diff --git a/apps/yaak-client/components/WebsocketRequestPane.tsx b/apps/yaak-client/components/WebsocketRequestPane.tsx
index 83e6c1d60..af004c3dc 100644
--- a/apps/yaak-client/components/WebsocketRequestPane.tsx
+++ b/apps/yaak-client/components/WebsocketRequestPane.tsx
@@ -21,6 +21,7 @@ import { useRequestUpdateKey } from "../hooks/useRequestUpdateKey";
 import { deepEqualAtom } from "../lib/atoms";
 import { languageFromContentType } from "../lib/contentType";
 import { generateId } from "../lib/generateId";
+import { extractPathPlaceholders } from "../lib/pathPlaceholders";
 import { prepareImportQuerystring } from "../lib/prepareImportQuerystring";
 import { resolvedModelName } from "../lib/resolvedModelName";
 import { CountBadge } from "./core/CountBadge";
@@ -83,9 +84,7 @@ export function WebsocketRequestPane({ style, fullHeight, className, activeReque
   );
 
   const { urlParameterPairs, urlParametersKey } = useMemo(() => {
-    const placeholderNames = Array.from(activeRequest.url.matchAll(/\/(:[^/]+)/g)).map(
-      (m) => m[1] ?? "",
-    );
+    const placeholderNames = extractPathPlaceholders(activeRequest.url);
     const nonEmptyParameters = activeRequest.urlParameters.filter((p) => p.name || p.value);
     const items: Pair[] = [...nonEmptyParameters];
     for (const name of placeholderNames) {
diff --git a/apps/yaak-client/components/core/Editor/twig/pathParameters.ts b/apps/yaak-client/components/core/Editor/twig/pathParameters.ts
index dc226adc4..ee41751a4 100644
--- a/apps/yaak-client/components/core/Editor/twig/pathParameters.ts
+++ b/apps/yaak-client/components/core/Editor/twig/pathParameters.ts
@@ -51,15 +51,20 @@ function pathParameters(
       to,
       enter(node) {
         if (node.name === "Text") {
-          // Find the `url` node and then jump into it to find the placeholders
+          // Find the URL overlay root. With `Host?` optional, a path-only URL like
+          // `/:foo/:bar` produces `Path` as the topmost overlay node instead of `url`,
+          // so accept either.
           for (let i = node.from; i < node.to; i++) {
             const innerTree = syntaxTree(view.state).resolveInner(i);
-            if (innerTree.node.name === "url") {
+            if (innerTree.node.name === "url" || innerTree.node.name === "Path") {
               innerTree.toTree().iterate({
                 enter(node) {
                   if (node.name !== "Placeholder") return;
                   const globalFrom = innerTree.node.from + node.from;
                   const globalTo = innerTree.node.from + node.to;
+                  // A real path placeholder is preceded by `/`. This filters mid-segment
+                  // Placeholder nodes (e.g. trailing `:literal` after `:id:literal`).
+                  if (view.state.doc.sliceString(globalFrom - 1, globalFrom) !== "/") return;
                   const rawText = view.state.doc.sliceString(globalFrom, globalTo);
                   const onClick = () => onClickPathParameter(rawText);
                   const widget = new PathPlaceholderWidget(rawText, globalFrom, onClick);
diff --git a/apps/yaak-client/components/core/Editor/url/highlight.ts b/apps/yaak-client/components/core/Editor/url/highlight.ts
index 69c8ac9be..5a49a9512 100644
--- a/apps/yaak-client/components/core/Editor/url/highlight.ts
+++ b/apps/yaak-client/components/core/Editor/url/highlight.ts
@@ -2,7 +2,10 @@ import { styleTags, tags as t } from "@lezer/highlight";
 
 export const highlight = styleTags({
   Protocol: t.comment,
-  Placeholder: t.emphasis,
+  // Placeholder nodes are rendered as chip widgets by `pathParameters.ts`, which
+  // replaces the underlying text — so a style on the text itself is invisible for
+  // valid placeholders and only ever appears on the spurious nodes the widget
+  // plugin filters out (e.g. the trailing `:literal` in `/:id:literal`).
   // PathSegment: t.tagName,
   // Host: t.variableName,
   // Path: t.bool,
diff --git a/apps/yaak-client/components/core/Editor/url/url.grammar b/apps/yaak-client/components/core/Editor/url/url.grammar
index 62c97dd85..8b28fd06b 100644
--- a/apps/yaak-client/components/core/Editor/url/url.grammar
+++ b/apps/yaak-client/components/core/Editor/url/url.grammar
@@ -1,6 +1,10 @@
-@top url { Protocol? Host Path? Query? }
+// Host is optional so URLs starting with `/` go straight to Path. Without this,
+// the parser error-recovers past the leading `/` and consumes the first segment as
+// Host (since Host's char class includes `:` for `host:port`), eating an initial
+// `:name` placeholder like `/:foo/:bar`.
+@top url { Protocol? Host? Path? Query? }
 
-Path { ("/" (Placeholder | PathSegment))+ }
+Path { ("/" (Placeholder PathSegment? | PathSegment))+ }
 
 Query { "?" queryPair ("&" queryPair)* }
 
@@ -9,7 +13,10 @@ Query { "?" queryPair ("&" queryPair)* }
     Host { $[a-zA-Z0-9-_.:\[\]]+ }
     @precedence { Protocol, Host }
 
-    Placeholder { ":" ![/?#]+ }
+    // Placeholder name excludes `:` so a literal colon ends the placeholder. `/:abc:def`
+    // parses as Placeholder(:abc) + PathSegment(:def). `/abc:def` is all literal since
+    // the segment doesn't start with `:`.
+    Placeholder { ":" ![/?#:]+ }
     PathSegment { ![?#/]+ }
     @precedence { Placeholder, PathSegment }
 
diff --git a/apps/yaak-client/components/core/Editor/url/url.terms.ts b/apps/yaak-client/components/core/Editor/url/url.terms.ts
index 159035e3d..8a57dd228 100644
--- a/apps/yaak-client/components/core/Editor/url/url.terms.ts
+++ b/apps/yaak-client/components/core/Editor/url/url.terms.ts
@@ -1,9 +1,9 @@
 // This file was generated by lezer-generator. You probably shouldn't edit it.
-export const url = 1,
+export const
+  url = 1,
   Protocol = 2,
   Host = 3,
-  Port = 4,
-  Path = 5,
-  Placeholder = 6,
-  PathSegment = 7,
-  Query = 8;
+  Path = 4,
+  Placeholder = 5,
+  PathSegment = 6,
+  Query = 7
diff --git a/apps/yaak-client/components/core/Editor/url/url.test.ts b/apps/yaak-client/components/core/Editor/url/url.test.ts
new file mode 100644
index 000000000..76d3f98c4
--- /dev/null
+++ b/apps/yaak-client/components/core/Editor/url/url.test.ts
@@ -0,0 +1,39 @@
+import { describe, expect, test } from "vite-plus/test";
+import { parser } from "./url";
+
+function placeholderStarts(input: string): number[] {
+  const positions: number[] = [];
+  parser
+    .parse(input)
+    .cursor()
+    .iterate((node) => {
+      if (node.name === "Placeholder") positions.push(node.from);
+    });
+  return positions;
+}
+
+describe("URL grammar Placeholder", () => {
+  test("recognized after `/`", () => {
+    const url = "https://x.com/users/:id";
+    const [pos] = placeholderStarts(url);
+    expect(url[pos - 1]).toBe("/");
+  });
+
+  test("lexer over-emits a second Placeholder after a literal `:` (filter relies on this)", () => {
+    const url = "https://x.com/x/:id:def";
+    const positions = placeholderStarts(url);
+    expect(positions.length).toBe(2);
+    expect(url[positions[0] - 1]).toBe("/");
+    expect(url[positions[1] - 1]).not.toBe("/");
+  });
+
+  test("first segment of a path-only URL is a Placeholder, not eaten as Host", () => {
+    // Regression: without `Host?`, the first `:chip1` would be tokenized as Host
+    // (Host's char class includes `:` for `host:port`), leaving only `:chip2` as
+    // a Placeholder.
+    const url = "/:chip1/:chip2";
+    const positions = placeholderStarts(url);
+    expect(positions.length).toBe(2);
+    expect(url.slice(positions[0])).toMatch(/^:chip1/);
+  });
+});
diff --git a/apps/yaak-client/components/core/Editor/url/url.ts b/apps/yaak-client/components/core/Editor/url/url.ts
index ad421be67..911b6646f 100644
--- a/apps/yaak-client/components/core/Editor/url/url.ts
+++ b/apps/yaak-client/components/core/Editor/url/url.ts
@@ -4,17 +4,17 @@ import { highlight } from "./highlight";
 export const parser = LRParser.deserialize({
   version: 14,
   states:
-    "!|OQOPOOQYOPOOOTOPOOObOQO'#CdOjOPO'#C`OuOSO'#CcQOOOOOQ]OPOOOOOO,59O,59OOOOO-E6b-E6bOzOPO,58}O!SOSO'#CeO!XOPO1G.iOOOO,59P,59POOOO-E6c-E6c",
-  stateData: "!g~OQQORPO~OZRO[TO~OTWOUWO~OZROYSX[SX~O]YO~O^ZOYVa~O]]O~O^ZOYVi~OQRTUT~",
-  goto: "nYPPPPZPP^bhRVPTUPVQSPRXSQ[YR^[",
+    "#YQQOPOOO`OQO'#CdOhOPO'#C`OsOSO'#CcQOOOOOQZOPOOQWOPOOQTOPOOOxOQO,59OOOOO,59O,59OOOOO-E6b-E6bO!WOPO,58}OOOO1G.j1G.jO!`OSO'#CeO!eOPO1G.iOOOO,59P,59POOOO-E6c-E6c",
+  stateData: "!s~OQVORUOZPO[RO~OTWOUXO~OZPOYSX[SX~O]ZO~OU[OYWaZWa[Wa~O^]OYVa~O]_O~O^]OYVi~OQRTUT~",
+  goto: "tYPPPPZPP`fnVTOUVXSOTUVUQOUVRYQQ^ZR`^",
   nodeNames: "⚠ url Protocol Host Path Placeholder PathSegment Query",
   maxTerm: 14,
   propSources: [highlight],
   skippedNodes: [0],
   repeatNodeCount: 2,
   tokenData:
-    ".i~RgOs!jtv!jvw#Xw}!j}!O#r!O!P#r!P!Q%U!Q![%Z![!]'o!]!a!j!a!b+W!b!c!j!c!}+]!}#O#r#O#P!j#P#Q#r#Q#R!j#R#S#r#S#T!j#T#o+]#o;'S!j;'S;=`#R<%lO!jQ!oUUQOs!jt!P!j!Q!a!j!b;'S!j;'S;=`#R<%lO!jQ#UP;=`<%l!jR#`U^PUQOs!jt!P!j!Q!a!j!b;'S!j;'S;=`#R<%lO!jR#ycRPUQOs!jt}!j}!O#r!O!P#r!Q![#r![!]#r!]!a!j!b!c!j!c!}#r!}#O#r#O#P!j#P#Q#r#Q#R!j#R#S#r#S#T!j#T#o#r#o;'S!j;'S;=`#R<%lO!j~%ZOZ~V%de]SRPUQOs!jt}!j}!O#r!O!P#r!Q![%Z![!]#r!]!_!j!_!`&u!`!a!j!b!c!j!c!}%Z!}#O#r#O#P!j#P#Q#r#Q#R!j#R#S#r#S#T!j#T#o%Z#o;'S!j;'S;=`#R<%lO!jU&|Z]SUQOs!jt!P!j!Q![&u![!a!j!b!c!j!c!}&u!}#T!j#T#o&u#o;'S!j;'S;=`#R<%lO!jR'vcRPUQOs)Rt})R}!O)r!O!P)r!Q![)r![!])r!]!a)R!b!c)R!c!})r!}#O)r#O#P)R#P#Q)r#Q#R)R#R#S)r#S#T)R#T#o)r#o;'S)R;'S;=`)l<%lO)RQ)YUTQUQOs)Rt!P)R!Q!a)R!b;'S)R;'S;=`)l<%lO)RQ)oP;=`<%l)RR){cRPTQUQOs)Rt})R}!O)r!O!P)r!Q![)r![!])r!]!a)R!b!c)R!c!})r!}#O)r#O#P)R#P#Q)r#Q#R)R#R#S)r#S#T)R#T#o)r#o;'S)R;'S;=`)l<%lO)R~+]O[~V+fe]SRPUQOs!jt}!j}!O#r!O!P#r!Q![%Z![!],w!]!_!j!_!`&u!`!a!j!b!c!j!c!}+]!}#O#r#O#P!j#P#Q#r#Q#R!j#R#S#r#S#T!j#T#o+]#o;'S!j;'S;=`#R<%lO!jR-OdRPUQOs!jt}!j}!O#r!O!P#r!P!Q.^!Q![#r![!]#r!]!a!j!b!c!j!c!}#r!}#O#r#O#P!j#P#Q#r#Q#R!j#R#S#r#S#T!j#T#o#r#o;'S!j;'S;=`#R<%lO!jP.aP!P!Q.dP.iOQP",
+    ".o~RgOs!jtv!jvw#Xw}!j}!O#r!O!P#r!P!Q%U!Q![%Z![!]'o!]!a!j!a!b+^!b!c!j!c!}+c!}#O#r#O#P!j#P#Q#r#Q#R!j#R#S#r#S#T!j#T#o+c#o;'S!j;'S;=`#R<%lO!jQ!oUUQOs!jt!P!j!Q!a!j!b;'S!j;'S;=`#R<%lO!jQ#UP;=`<%l!jR#`U^PUQOs!jt!P!j!Q!a!j!b;'S!j;'S;=`#R<%lO!jR#ycRPUQOs!jt}!j}!O#r!O!P#r!Q![#r![!]#r!]!a!j!b!c!j!c!}#r!}#O#r#O#P!j#P#Q#r#Q#R!j#R#S#r#S#T!j#T#o#r#o;'S!j;'S;=`#R<%lO!j~%ZOZ~V%de]SRPUQOs!jt}!j}!O#r!O!P#r!Q![%Z![!]#r!]!_!j!_!`&u!`!a!j!b!c!j!c!}%Z!}#O#r#O#P!j#P#Q#r#Q#R!j#R#S#r#S#T!j#T#o%Z#o;'S!j;'S;=`#R<%lO!jU&|Z]SUQOs!jt!P!j!Q![&u![!a!j!b!c!j!c!}&u!}#T!j#T#o&u#o;'S!j;'S;=`#R<%lO!jR'vcRPUQOs)Rt})R}!O)x!O!P)x!Q![)x![!]#r!]!a)R!b!c)R!c!})x!}#O)x#O#P)R#P#Q)x#Q#R)R#R#S)x#S#T)R#T#o)x#o;'S)R;'S;=`)r<%lO)RQ)YWTQUQOs)Rt!P)R!Q![)R![!]!j!]!a)R!b;'S)R;'S;=`)r<%lO)RQ)uP;=`<%l)RR*RcRPTQUQOs)Rt})R}!O)x!O!P)x!Q![)x![!]#r!]!a)R!b!c)R!c!})x!}#O)x#O#P)R#P#Q)x#Q#R)R#R#S)x#S#T)R#T#o)x#o;'S)R;'S;=`)r<%lO)R~+cO[~V+le]SRPUQOs!jt}!j}!O#r!O!P#r!Q![%Z![!],}!]!_!j!_!`&u!`!a!j!b!c!j!c!}+c!}#O#r#O#P!j#P#Q#r#Q#R!j#R#S#r#S#T!j#T#o+c#o;'S!j;'S;=`#R<%lO!jR-UdRPUQOs!jt}!j}!O#r!O!P#r!P!Q.d!Q![#r![!]#r!]!a!j!b!c!j!c!}#r!}#O#r#O#P!j#P#Q#r#Q#R!j#R#S#r#S#T!j#T#o#r#o;'S!j;'S;=`#R<%lO!jP.gP!P!Q.jP.oOQP",
   tokenizers: [0, 1, 2],
   topRules: { url: [0, 1] },
-  tokenPrec: 63,
+  tokenPrec: 75,
 });
diff --git a/apps/yaak-client/lib/pathPlaceholders.test.ts b/apps/yaak-client/lib/pathPlaceholders.test.ts
new file mode 100644
index 000000000..3c74b3151
--- /dev/null
+++ b/apps/yaak-client/lib/pathPlaceholders.test.ts
@@ -0,0 +1,28 @@
+import { describe, expect, test } from "vite-plus/test";
+import { extractPathPlaceholders } from "./pathPlaceholders";
+
+describe("extractPathPlaceholders", () => {
+  test("extracts a single placeholder", () => {
+    expect(extractPathPlaceholders("/users/:id")).toEqual([":id"]);
+  });
+
+  test("extracts multiple placeholders", () => {
+    expect(extractPathPlaceholders("/users/:id/posts/:postId")).toEqual([":id", ":postId"]);
+  });
+
+  test("stops at a literal `:` in the same segment", () => {
+    expect(extractPathPlaceholders("/tasks/:id:cancel")).toEqual([":id"]);
+  });
+
+  test("does not match `:foo` mid-segment", () => {
+    expect(extractPathPlaceholders("/users/abc:def")).toEqual([]);
+  });
+
+  test("does not match `:` in a host port", () => {
+    expect(extractPathPlaceholders("https://example.com:8080/users/:id")).toEqual([":id"]);
+  });
+
+  test("returns empty for a URL with no placeholders", () => {
+    expect(extractPathPlaceholders("https://example.com/foo/bar?q=1#hash")).toEqual([]);
+  });
+});
diff --git a/apps/yaak-client/lib/pathPlaceholders.ts b/apps/yaak-client/lib/pathPlaceholders.ts
new file mode 100644
index 000000000..f6dab4de2
--- /dev/null
+++ b/apps/yaak-client/lib/pathPlaceholders.ts
@@ -0,0 +1,14 @@
+/**
+ * Extract `:name`-style path placeholders from a URL string.
+ *
+ * A placeholder is `:` followed by one-or-more characters that are not `/`, `?`,
+ * `#`, or `:`. The `:` boundary means a placeholder ends where a literal colon
+ * starts in the same segment, e.g. `/tasks/:id:increment-importance` yields one
+ * placeholder `:id` and `:increment-importance` is literal text.
+ *
+ * Only `:` that sits at the start of a `/`-delimited segment counts — `/abc:def`
+ * has no placeholders. Returned names include the leading colon.
+ */
+export function extractPathPlaceholders(url: string): string[] {
+  return Array.from(url.matchAll(/\/(:[^/?#:]+)/g)).map((m) => m[1] ?? "");
+}
diff --git a/crates/yaak-http/src/path_placeholders.rs b/crates/yaak-http/src/path_placeholders.rs
index 9a700e82c..25aee7896 100644
--- a/crates/yaak-http/src/path_placeholders.rs
+++ b/crates/yaak-http/src/path_placeholders.rs
@@ -34,7 +34,10 @@ fn replace_path_placeholder(p: &HttpUrlParameter, url: &str) -> String {
         return url.to_string();
     }
 
-    let re = regex::Regex::new(format!("(/){}([/?#]|$)", p.name).as_str()).unwrap();
+    // A path placeholder is terminated by `/`, `?`, `#`, end-of-string, or a literal `:`.
+    // The `:` boundary is what lets `/:id:increment-importance` substitute the `:id`
+    // placeholder while leaving `:increment-importance` as literal text.
+    let re = regex::Regex::new(format!("(/){}([/?#:]|$)", p.name).as_str()).unwrap();
     let result = re
         .replace_all(url, |cap: &regex::Captures| {
             format!(
@@ -83,6 +86,18 @@ mod placeholder_tests {
         );
     }
 
+    #[test]
+    fn placeholder_followed_by_literal_colon() {
+        // AIP-136-style custom method: `:id` is the placeholder, `:increment-importance`
+        // is literal text in the same path segment.
+        let p =
+            HttpUrlParameter { name: ":id".into(), value: "42".into(), enabled: true, id: None };
+        assert_eq!(
+            replace_path_placeholder(&p, "https://example.com/tasks/:id:increment-importance"),
+            "https://example.com/tasks/42:increment-importance",
+        );
+    }
+
     #[test]
     fn placeholder_missing() {
         let p = HttpUrlParameter {