diff --git a/crates/yaak-http/src/types.rs b/crates/yaak-http/src/types.rs
index d7931684..a9d85397 100644
--- a/crates/yaak-http/src/types.rs
+++ b/crates/yaak-http/src/types.rs
@@ -78,8 +78,19 @@ impl SendableHttpRequest {
     }
 
     pub fn insert_header(&mut self, header: (String, String)) {
+        if header.0.eq_ignore_ascii_case("cookie") {
+            if let Some(existing) =
+                self.headers.iter_mut().find(|h| h.0.eq_ignore_ascii_case("cookie"))
+            {
+                existing.1 = format!("{}; {}", existing.1, header.1);
+            } else {
+                self.headers.push(header);
+            }
+            return;
+        }
+
         if let Some(existing) =
-            self.headers.iter_mut().find(|h| h.0.to_lowercase() == header.0.to_lowercase())
+            self.headers.iter_mut().find(|h| h.0.eq_ignore_ascii_case(&header.0))
         {
             existing.1 = header.1;
         } else {
@@ -494,7 +505,76 @@ mod tests {
     use bytes::Bytes;
     use serde_json::json;
     use std::collections::BTreeMap;
-    use yaak_models::models::{HttpRequest, HttpUrlParameter};
+    use yaak_models::models::{HttpRequest, HttpRequestHeader, HttpUrlParameter};
+
+    #[tokio::test]
+    async fn test_sendable_request_preserves_independent_cookie_enabled_states() {
+        let request = HttpRequest {
+            url: "https://example.com/api".to_string(),
+            headers: vec![
+                HttpRequestHeader {
+                    enabled: true,
+                    name: "Cookie".to_string(),
+                    value: "session=abc".to_string(),
+                    id: None,
+                },
+                HttpRequestHeader {
+                    enabled: false,
+                    name: "Cookie".to_string(),
+                    value: "debug=verbose".to_string(),
+                    id: None,
+                },
+            ],
+            ..Default::default()
+        };
+
+        let sendable =
+            SendableHttpRequest::from_http_request(&request, SendableHttpRequestOptions::default())
+                .await
+                .unwrap();
+
+        assert_eq!(sendable.headers, vec![("Cookie".to_string(), "session=abc".to_string())]);
+    }
+
+    #[test]
+    fn test_insert_header_appends_authentication_cookie() {
+        let mut request = SendableHttpRequest {
+            headers: vec![
+                ("Cookie".to_string(), "session=abc".to_string()),
+                ("Cookie".to_string(), "theme=dark".to_string()),
+            ],
+            ..Default::default()
+        };
+
+        request.insert_header(("cookie".to_string(), "api_key=secret".to_string()));
+
+        assert_eq!(
+            request.headers,
+            vec![
+                ("Cookie".to_string(), "session=abc; api_key=secret".to_string()),
+                ("Cookie".to_string(), "theme=dark".to_string()),
+            ],
+        );
+    }
+
+    #[tokio::test]
+    async fn test_sendable_request_preserves_serialized_path_delimiters() {
+        let request = HttpRequest {
+            url: "https://example.com/labels/.one%2Ftwo.three/matrix/;x=1%3Bspoof%3D2;y=2"
+                .to_string(),
+            ..Default::default()
+        };
+
+        let sendable =
+            SendableHttpRequest::from_http_request(&request, SendableHttpRequestOptions::default())
+                .await
+                .unwrap();
+
+        assert_eq!(
+            sendable.url,
+            "https://example.com/labels/.one%2Ftwo.three/matrix/;x=1%3Bspoof%3D2;y=2",
+        );
+    }
 
     #[test]
     fn test_build_url_no_params() {
diff --git a/crates/yaak-models/src/queries/folders.rs b/crates/yaak-models/src/queries/folders.rs
index a26e3379..bc5bd389 100644
--- a/crates/yaak-models/src/queries/folders.rs
+++ b/crates/yaak-models/src/queries/folders.rs
@@ -1,4 +1,4 @@
-use super::conflict_free_name;
+use super::{conflict_free_name, merge_headers};
 use crate::client_db::ClientDb;
 use crate::connection_or_tx::ConnectionOrTx;
 use crate::error::Result;
@@ -144,9 +144,7 @@ impl<'a> ClientDb<'a> {
             headers.append(&mut workspace_headers);
         }
 
-        headers.append(&mut folder.headers.clone());
-
-        Ok(headers)
+        Ok(merge_headers(headers, folder.headers.clone()))
     }
 
     pub fn resolve_settings_for_folder(
diff --git a/crates/yaak-models/src/queries/grpc_requests.rs b/crates/yaak-models/src/queries/grpc_requests.rs
index f54635b4..593e128f 100644
--- a/crates/yaak-models/src/queries/grpc_requests.rs
+++ b/crates/yaak-models/src/queries/grpc_requests.rs
@@ -1,4 +1,4 @@
-use super::{conflict_free_name, dedupe_headers};
+use super::{conflict_free_name, merge_headers};
 use crate::client_db::ClientDb;
 use crate::error::Result;
 use crate::models::{
@@ -110,9 +110,7 @@ impl<'a> ClientDb<'a> {
             metadata.append(&mut workspace_metadata);
         }
 
-        metadata.append(&mut grpc_request.metadata.clone());
-
-        Ok(dedupe_headers(metadata))
+        Ok(merge_headers(metadata, grpc_request.metadata.clone()))
     }
 
     pub fn resolve_settings_for_grpc_request(
diff --git a/crates/yaak-models/src/queries/http_requests.rs b/crates/yaak-models/src/queries/http_requests.rs
index 6130ec67..d4e0d6d7 100644
--- a/crates/yaak-models/src/queries/http_requests.rs
+++ b/crates/yaak-models/src/queries/http_requests.rs
@@ -1,4 +1,4 @@
-use super::{conflict_free_name, dedupe_headers};
+use super::{conflict_free_name, merge_headers};
 use crate::client_db::ClientDb;
 use crate::error::Result;
 use crate::models::{
@@ -96,9 +96,7 @@ impl<'a> ClientDb<'a> {
             headers.append(&mut workspace_headers);
         }
 
-        headers.append(&mut http_request.headers.clone());
-
-        Ok(dedupe_headers(headers))
+        Ok(merge_headers(headers, http_request.headers.clone()))
     }
 
     pub fn resolve_settings_for_http_request(
@@ -172,3 +170,44 @@ impl<'a> ClientDb<'a> {
         Ok(children)
     }
 }
+
+#[cfg(test)]
+mod tests {
+    use crate::init_in_memory;
+    use crate::models::{HttpRequest, HttpRequestHeader};
+
+    #[test]
+    fn request_resolution_preserves_duplicate_request_headers() {
+        let (query_manager, _blob_manager, _rx) = init_in_memory().expect("Failed to init DB");
+        let db = query_manager.connect();
+        let workspace = db.list_workspaces().expect("Failed to list workspaces").remove(0);
+        let request = HttpRequest {
+            workspace_id: workspace.id,
+            headers: vec![
+                HttpRequestHeader {
+                    name: "Cookie".to_string(),
+                    value: "required=1".to_string(),
+                    ..Default::default()
+                },
+                HttpRequestHeader {
+                    enabled: false,
+                    name: "Cookie".to_string(),
+                    value: "optional=1".to_string(),
+                    ..Default::default()
+                },
+            ],
+            ..Default::default()
+        };
+
+        let resolved = db.resolve_headers_for_http_request(&request).expect("Failed to resolve");
+        let cookies = resolved
+            .iter()
+            .filter(|header| header.name.eq_ignore_ascii_case("cookie"))
+            .collect::<Vec<_>>();
+
+        assert_eq!(cookies.len(), 2);
+        assert_eq!(cookies[0].value, "required=1");
+        assert_eq!(cookies[1].value, "optional=1");
+        assert!(!cookies[1].enabled);
+    }
+}
diff --git a/crates/yaak-models/src/queries/mod.rs b/crates/yaak-models/src/queries/mod.rs
index 2b6bdc43..e2e8dabc 100644
--- a/crates/yaak-models/src/queries/mod.rs
+++ b/crates/yaak-models/src/queries/mod.rs
@@ -28,21 +28,59 @@ pub(crate) use duplicate_name::conflict_free_name;
 const MAX_HISTORY_ITEMS: usize = 20;
 
 use crate::models::HttpRequestHeader;
-use std::collections::HashMap;
+use std::collections::HashSet;
 
-/// Deduplicate headers by name (case-insensitive), keeping the latest (most specific) value.
-/// Preserves the order of first occurrence for each header name.
-pub(crate) fn dedupe_headers(headers: Vec<HttpRequestHeader>) -> Vec<HttpRequestHeader> {
-    let mut index_by_name: HashMap<String, usize> = HashMap::new();
-    let mut deduped: Vec<HttpRequestHeader> = Vec::new();
-    for header in headers {
-        let key = header.name.to_lowercase();
-        if let Some(&idx) = index_by_name.get(&key) {
-            deduped[idx] = header;
-        } else {
-            index_by_name.insert(key, deduped.len());
-            deduped.push(header);
-        }
-    }
-    deduped
+/// Merge a more-specific header layer over its parent. Names in the child replace
+/// inherited values case-insensitively, while duplicates declared together in
+/// either layer remain independent entries.
+pub(crate) fn merge_headers(
+    mut parent: Vec<HttpRequestHeader>,
+    child: Vec<HttpRequestHeader>,
+) -> Vec<HttpRequestHeader> {
+    let child_names = child.iter().map(|header| header.name.to_lowercase()).collect::<HashSet<_>>();
+    parent.retain(|header| !child_names.contains(&header.name.to_lowercase()));
+    parent.extend(child);
+    parent
+}
+
+#[cfg(test)]
+mod tests {
+    use super::merge_headers;
+    use crate::models::HttpRequestHeader;
+
+    fn header(name: &str, value: &str) -> HttpRequestHeader {
+        HttpRequestHeader { name: name.to_string(), value: value.to_string(), ..Default::default() }
+    }
+
+    #[test]
+    fn preserves_duplicate_headers_declared_in_one_layer() {
+        let merged = merge_headers(
+            vec![header("Cookie", "inherited=1")],
+            vec![
+                header("Cookie", "required=1"),
+                header("cookie", "optional=1"),
+            ],
+        );
+
+        assert_eq!(
+            merged.iter().map(|header| header.value.as_str()).collect::<Vec<_>>(),
+            vec!["required=1", "optional=1"],
+        );
+    }
+
+    #[test]
+    fn child_names_override_parent_names_without_affecting_other_headers() {
+        let merged = merge_headers(
+            vec![header("Accept", "*/*"), header("X-Parent", "kept")],
+            vec![header("accept", "application/json")],
+        );
+
+        assert_eq!(
+            merged
+                .iter()
+                .map(|header| (header.name.as_str(), header.value.as_str()))
+                .collect::<Vec<_>>(),
+            vec![("X-Parent", "kept"), ("accept", "application/json")],
+        );
+    }
 }
diff --git a/crates/yaak-models/src/queries/websocket_requests.rs b/crates/yaak-models/src/queries/websocket_requests.rs
index 3ef4c16d..1dcf752f 100644
--- a/crates/yaak-models/src/queries/websocket_requests.rs
+++ b/crates/yaak-models/src/queries/websocket_requests.rs
@@ -1,4 +1,4 @@
-use super::{conflict_free_name, dedupe_headers};
+use super::{conflict_free_name, merge_headers};
 use crate::client_db::ClientDb;
 use crate::error::Result;
 use crate::models::{
@@ -103,13 +103,9 @@ impl<'a> ClientDb<'a> {
         &self,
         websocket_request: &WebsocketRequest,
     ) -> Result<Vec<HttpRequestHeader>> {
-        let workspace = self.get_workspace(&websocket_request.workspace_id)?;
-
         // Resolved headers should be from furthest to closest ancestor, to override logically.
         let mut headers = Vec::new();
 
-        headers.append(&mut workspace.headers.clone());
-
         if let Some(folder_id) = websocket_request.folder_id.clone() {
             let parent_folder = self.get_folder(&folder_id)?;
             let mut folder_headers = self.resolve_headers_for_folder(&parent_folder)?;
@@ -120,9 +116,7 @@ impl<'a> ClientDb<'a> {
             headers.append(&mut workspace_headers);
         }
 
-        headers.append(&mut websocket_request.headers.clone());
-
-        Ok(dedupe_headers(headers))
+        Ok(merge_headers(headers, websocket_request.headers.clone()))
     }
 
     pub fn resolve_settings_for_websocket_request(
diff --git a/crates/yaak-models/src/queries/workspaces.rs b/crates/yaak-models/src/queries/workspaces.rs
index 50deb620..6ed7a262 100644
--- a/crates/yaak-models/src/queries/workspaces.rs
+++ b/crates/yaak-models/src/queries/workspaces.rs
@@ -1,3 +1,4 @@
+use super::merge_headers;
 use crate::blob_manager::BlobManager;
 use crate::client_db::ClientDb;
 use crate::error::Result;
@@ -144,9 +145,7 @@ impl<'a> ClientDb<'a> {
     }
 
     pub fn resolve_headers_for_workspace(&self, workspace: &Workspace) -> Vec<HttpRequestHeader> {
-        let mut headers = default_headers();
-        headers.extend(workspace.headers.clone());
-        headers
+        merge_headers(default_headers(), workspace.headers.clone())
     }
 
     pub fn resolve_settings_for_workspace(
diff --git a/plugins/importer-openapi/src/index.ts b/plugins/importer-openapi/src/index.ts
index 920c0288..8253022f 100644
--- a/plugins/importer-openapi/src/index.ts
+++ b/plugins/importer-openapi/src/index.ts
@@ -302,7 +302,7 @@ function importOperation({
     useDynamicServerUrls,
   });
   const urlParameters = [
-    ...importUrlParameters({ importState, parameters }),
+    ...importUrlParameters({ importState, parameters, path }),
     ...authentication.urlParameters,
   ];
   const headers = mergeHeaders(
@@ -336,6 +336,8 @@ function importOperation({
     url: buildOperationUrl(
       operationBaseUrl({ operation, pathItem, requestBaseUrl, serverOverrides }),
       path,
+      parameters,
+      importState,
     ),
     urlParameters,
     headers,
@@ -645,8 +647,58 @@ function findOrCreateFolderId({
   return folder.id;
 }
 
-function buildOperationUrl(baseUrl: string, path: string): string {
-  return joinUrlParts(baseUrl, path.replaceAll(/{([^}/]+)}/g, ":$1"));
+function buildOperationUrl(
+  baseUrl: string,
+  path: string,
+  parameters: unknown[],
+  importState: ImportState,
+): string {
+  let serializedPath = path;
+  for (const rawParameter of parameters) {
+    const parameter = importState.resolve(rawParameter);
+    if (!isRecord(parameter) || !shouldInlinePathParameter(parameter, importState, path)) continue;
+
+    const name = stringAt(parameter, "name") ?? "";
+    if (name.length === 0) continue;
+    const value = parameterExampleValue(parameter, importState);
+    serializedPath = serializedPath.replaceAll(
+      `{${name}}`,
+      isRecord(parameter.content)
+        ? encodePathComponent(serializeContentParameter(parameter, importState))
+        : serializePathParameter(name, value, parameter, encodePathComponent),
+    );
+  }
+  return joinUrlParts(baseUrl, serializedPath.replaceAll(/{([^}/]+)}/g, ":$1"));
+}
+
+function shouldInlinePathParameter(
+  parameter: UnknownRecord,
+  importState: ImportState,
+  path: string,
+): boolean {
+  if (stringAt(parameter, "in") !== "path") return false;
+  const name = stringAt(parameter, "name") ?? "";
+  const template = `{${name}}`;
+  const matchingSegments = path.split("/").filter((segment) => segment.includes(template));
+  if (matchingSegments.length === 0 || matchingSegments.some((segment) => segment !== template)) {
+    return true;
+  }
+  if (isRecord(parameter.content)) return false;
+  const value = parameterExampleValue(parameter, importState);
+  const style = stringAt(parameter, "style");
+  return (
+    style === "label" ||
+    style === "matrix" ||
+    Array.isArray(value) ||
+    isRecord(value)
+  );
+}
+
+function encodePathComponent(value: unknown): string {
+  return encodeURIComponent(stringifyExampleValue(value)).replace(
+    /[!'()*]/g,
+    (character) => `%${character.charCodeAt(0).toString(16).toUpperCase()}`,
+  );
 }
 
 function importBaseUrl(spec: UnknownRecord): string {
@@ -733,25 +785,82 @@ function trimTrailingSlashes(value: string): string {
 function importUrlParameters({
   importState,
   parameters,
+  path,
 }: {
   importState: ImportState;
   parameters: unknown[];
+  path: string;
 }): HttpUrlParameter[] {
   return parameters
     .map((p) => importState.resolve(p))
     .filter(isRecord)
     .filter((p) => stringAt(p, "in") === "query" || stringAt(p, "in") === "path")
-    .map((p) => ({
-      enabled: p.required === true,
-      name:
-        stringAt(p, "in") === "path"
-          ? `:${stringAt(p, "name") ?? ""}`
-          : (stringAt(p, "name") ?? ""),
-      value: parameterExample(p, importState),
-    }))
+    .flatMap((p) => serializeUrlParameter(p, importState, path))
     .filter(({ name }) => name.length > 0);
 }
 
+function serializeUrlParameter(
+  parameter: UnknownRecord,
+  importState: ImportState,
+  path: string,
+): HttpUrlParameter[] {
+  const name = stringAt(parameter, "name") ?? "";
+  const location = stringAt(parameter, "in");
+  const enabled = parameter.required === true;
+  const value = parameterExampleValue(parameter, importState);
+  if (isRecord(parameter.content)) {
+    return [
+      {
+        enabled,
+        name: location === "path" ? `:${name}` : name,
+        value: serializeContentParameter(parameter, importState),
+      },
+    ];
+  }
+  if (location === "path") {
+    if (shouldInlinePathParameter(parameter, importState, path)) return [];
+    return [{ enabled, name: `:${name}`, value: serializePathParameter(name, value, parameter) }];
+  }
+
+  if (isRecord(value)) {
+    const entries = Object.entries(value);
+    const style = stringAt(parameter, "style") ?? "form";
+    const explode = parameter.explode !== false;
+    if (style === "deepObject") {
+      return entries.map(([key, entryValue]) => ({
+        enabled,
+        name: `${name}[${key}]`,
+        value: stringifyExampleValue(entryValue),
+      }));
+    }
+    if (style === "form" && explode) {
+      return entries.map(([key, entryValue]) => ({
+        enabled,
+        name: key,
+        value: stringifyExampleValue(entryValue),
+      }));
+    }
+    const separator = style === "spaceDelimited" ? " " : style === "pipeDelimited" ? "|" : ",";
+    return [{ enabled, name, value: entries.flat().map(stringifyExampleValue).join(separator) }];
+  }
+
+  if (Array.isArray(value)) {
+    const style = stringAt(parameter, "style") ?? "form";
+    const explode = parameter.explode !== false;
+    if (style === "form" && explode) {
+      return value.map((entryValue) => ({
+        enabled,
+        name,
+        value: stringifyExampleValue(entryValue),
+      }));
+    }
+    const separator = style === "spaceDelimited" ? " " : style === "pipeDelimited" ? "|" : ",";
+    return [{ enabled, name, value: value.map(stringifyExampleValue).join(separator) }];
+  }
+
+  return [{ enabled, name, value: stringifyExampleValue(value) }];
+}
+
 function importHeaderParameters({
   importState,
   parameters,
@@ -763,18 +872,138 @@ function importHeaderParameters({
     .map((p) => importState.resolve(p))
     .filter(isRecord)
     .filter((p) => stringAt(p, "in") === "header")
+    .filter(
+      (p) =>
+        !["accept", "authorization", "content-type"].includes(
+          (stringAt(p, "name") ?? "").toLowerCase(),
+        ),
+    )
     .map((p) => ({
       enabled: p.required === true,
       name: stringAt(p, "name") ?? "",
-      value: parameterExample(p, importState),
+      value: serializeParameterValue(p, importState),
     }))
-    .filter(({ name }) => name.length > 0);
+    .filter(({ name }) => name.length > 0)
+    .concat(importCookieHeader(parameters, importState));
+}
+
+function importCookieHeader(parameters: unknown[], importState: ImportState): HttpRequestHeader[] {
+  return parameters
+    .map((p) => importState.resolve(p))
+    .filter(isRecord)
+    .filter((p) => stringAt(p, "in") === "cookie")
+    .map((p) => ({
+      enabled: p.required === true,
+      name: "Cookie",
+      value: serializeCookieParameter(p, importState),
+    }))
+    .filter(({ value }) => value.length > 0);
+}
+
+function serializeCookieParameter(parameter: UnknownRecord, importState: ImportState): string {
+  const name = stringAt(parameter, "name") ?? "";
+  if (name.length === 0) return "";
+  if (isRecord(parameter.content)) {
+    return `${name}=${serializeContentParameter(parameter, importState)}`;
+  }
+
+  const value = parameterExampleValue(parameter, importState);
+  const explode = parameter.explode !== false;
+  if (Array.isArray(value)) {
+    return explode
+      ? value.map((entryValue) => `${name}=${stringifyExampleValue(entryValue)}`).join("&")
+      : `${name}=${value.map(stringifyExampleValue).join(",")}`;
+  }
+  if (isRecord(value)) {
+    const entries = Object.entries(value);
+    return explode
+      ? entries.map(([key, entryValue]) => `${key}=${stringifyExampleValue(entryValue)}`).join("&")
+      : `${name}=${entries.flat().map(stringifyExampleValue).join(",")}`;
+  }
+  return `${name}=${stringifyExampleValue(value)}`;
+}
+
+function serializeParameterValue(parameter: UnknownRecord, importState: ImportState): string {
+  if (isRecord(parameter.content)) return serializeContentParameter(parameter, importState);
+  return serializeSimpleParameter(parameterExampleValue(parameter, importState), parameter);
+}
+
+function serializeContentParameter(parameter: UnknownRecord, importState: ImportState): string {
+  const [contentType, rawMediaType] = Object.entries(toRecord(parameter.content))[0] ?? [];
+  const value = mediaTypeExample(toRecord(rawMediaType), importState);
+  return contentType?.toLowerCase().includes("json")
+    ? (JSON.stringify(value) ?? "")
+    : stringifyExampleValue(value);
+}
+
+function serializePathParameter(
+  name: string,
+  value: unknown,
+  parameter: UnknownRecord,
+  serializeValue: (value: unknown) => string = stringifyExampleValue,
+): string {
+  const style = stringAt(parameter, "style") ?? "simple";
+  const explode = parameter.explode === true;
+  const values = Array.isArray(value)
+    ? value.map(serializeValue)
+    : isRecord(value)
+      ? Object.entries(value).flatMap(([key, entryValue]) => [
+          serializeValue(key),
+          serializeValue(entryValue),
+        ])
+      : [serializeValue(value)];
+
+  if (style === "label") {
+    if (explode && isRecord(value)) {
+      return `.${Object.entries(value)
+        .map(([key, entryValue]) => `${serializeValue(key)}=${serializeValue(entryValue)}`)
+        .join(".")}`;
+    }
+    return `.${values.join(explode ? "." : ",")}`;
+  }
+  if (style === "matrix") {
+    if (explode && Array.isArray(value)) {
+      return value.map((entryValue) => `;${name}=${serializeValue(entryValue)}`).join("");
+    }
+    if (explode && isRecord(value)) {
+      return Object.entries(value)
+        .map(([key, entryValue]) => `;${serializeValue(key)}=${serializeValue(entryValue)}`)
+        .join("");
+    }
+    return `;${name}=${values.join(",")}`;
+  }
+  return serializeSimpleParameter(value, parameter, serializeValue);
+}
+
+function serializeSimpleParameter(
+  value: unknown,
+  parameter: UnknownRecord,
+  serializeValue: (value: unknown) => string = stringifyExampleValue,
+): string {
+  if (Array.isArray(value)) return value.map(serializeValue).join(",");
+  if (isRecord(value)) {
+    const entries = Object.entries(value);
+    return parameter.explode === true
+      ? entries
+          .map(([key, entryValue]) => `${serializeValue(key)}=${serializeValue(entryValue)}`)
+          .join(",")
+      : entries.flat().map(serializeValue).join(",");
+  }
+  return serializeValue(value);
 }
 
 function parameterExample(parameter: UnknownRecord, importState: ImportState): string {
+  return stringifyExampleValue(parameterExampleValue(parameter, importState));
+}
+
+function parameterExampleValue(parameter: UnknownRecord, importState: ImportState): unknown {
   const directExample = firstPresent(parameter.example, firstExampleValue(parameter.examples));
-  if (directExample != null) return stringifyExampleValue(directExample);
-  return stringifyExampleValue(schemaToExample(importState.resolve(parameter.schema), importState));
+  if (directExample != null) return directExample;
+  if (isRecord(parameter.content)) {
+    const mediaType = toRecord(Object.values(parameter.content)[0]);
+    return mediaTypeExample(mediaType, importState);
+  }
+  return schemaToExample(importState.resolve(parameter.schema), importState);
 }
 
 function importBody({
@@ -1374,10 +1603,13 @@ function buildOAuthVariablesByScheme(
 
 function mergeHeaders(...headerGroups: HttpRequestHeader[][]): HttpRequestHeader[] {
   const headers: HttpRequestHeader[] = [];
-  for (const header of headerGroups.flat()) {
-    const existing = headers.find((h) => h.name.toLowerCase() === header.name.toLowerCase());
-    if (existing == null) {
-      headers.push(header);
+  for (const group of headerGroups) {
+    const namesFromEarlierGroups = new Set(headers.map((header) => header.name.toLowerCase()));
+    for (const header of group) {
+      const name = header.name.toLowerCase();
+      if (name === "cookie" || !namesFromEarlierGroups.has(name)) {
+        headers.push(header);
+      }
     }
   }
   return headers;
diff --git a/plugins/importer-openapi/tests/__snapshots__/index.test.ts.snap b/plugins/importer-openapi/tests/__snapshots__/index.test.ts.snap
index 86a2eff5..121a8bee 100644
--- a/plugins/importer-openapi/tests/__snapshots__/index.test.ts.snap
+++ b/plugins/importer-openapi/tests/__snapshots__/index.test.ts.snap
@@ -163,18 +163,13 @@ Responses:
         "model": "http_request",
         "name": "Retrieve one version of a particular API",
         "sortPriority": 5,
-        "url": "\${[baseUrl]}/specs/:provider/:api.json",
+        "url": "\${[baseUrl]}/specs/:provider/2.1.0.json",
         "urlParameters": [
           {
             "enabled": true,
             "name": ":provider",
             "value": "apis.guru",
           },
-          {
-            "enabled": true,
-            "name": ":api",
-            "value": "2.1.0",
-          },
         ],
         "workspaceId": "GENERATE_ID::WORKSPACE_0",
       },
@@ -207,7 +202,7 @@ Responses:
         "model": "http_request",
         "name": "Retrieve one version of a particular API with a serviceName.",
         "sortPriority": 6,
-        "url": "\${[baseUrl]}/specs/:provider/:service/:api.json",
+        "url": "\${[baseUrl]}/specs/:provider/:service/2.1.0.json",
         "urlParameters": [
           {
             "enabled": true,
@@ -219,11 +214,6 @@ Responses:
             "name": ":service",
             "value": "graph",
           },
-          {
-            "enabled": true,
-            "name": ":api",
-            "value": "2.1.0",
-          },
         ],
         "workspaceId": "GENERATE_ID::WORKSPACE_0",
       },
@@ -256,14 +246,8 @@ Responses:
         "model": "http_request",
         "name": "List all APIs for a particular provider",
         "sortPriority": 7,
-        "url": "\${[baseUrl]}/:provider.json",
-        "urlParameters": [
-          {
-            "enabled": true,
-            "name": ":provider",
-            "value": "apis.guru",
-          },
-        ],
+        "url": "\${[baseUrl]}/apis.guru.json",
+        "urlParameters": [],
         "workspaceId": "GENERATE_ID::WORKSPACE_0",
       },
       {
@@ -860,13 +844,7 @@ Responses:
 - 200: Sucessful authentication.
 - 401: Unsuccessful authentication.",
         "folderId": "GENERATE_ID::FOLDER_1",
-        "headers": [
-          {
-            "enabled": false,
-            "name": "Authorization",
-            "value": "",
-          },
-        ],
+        "headers": [],
         "id": "GENERATE_ID::HTTP_REQUEST_15",
         "method": "GET",
         "model": "http_request",
diff --git a/plugins/importer-openapi/tests/index.test.ts b/plugins/importer-openapi/tests/index.test.ts
index deabbfba..8043eb62 100644
--- a/plugins/importer-openapi/tests/index.test.ts
+++ b/plugins/importer-openapi/tests/index.test.ts
@@ -766,6 +766,194 @@ describe("importer-openapi", () => {
     ]);
   });
 
+  test("Imports cookie and content-based parameters", async () => {
+    const imported = await convertOpenApi(
+      JSON.stringify({
+        openapi: "3.0.4",
+        info: { title: "Parameter Test", version: "1.0.0" },
+        paths: {
+          "/items": {
+            get: {
+              parameters: [
+                {
+                  name: "session",
+                  in: "cookie",
+                  required: true,
+                  schema: { type: "string", example: "abc" },
+                },
+                {
+                  name: "debug",
+                  in: "cookie",
+                  schema: { type: "string", example: "verbose" },
+                },
+                {
+                  name: "X-Filter",
+                  in: "header",
+                  required: true,
+                  content: { "text/plain": { example: "active" } },
+                },
+              ],
+              responses: {},
+            },
+          },
+        },
+      }),
+    );
+
+    expect(imported?.resources.httpRequests[0]?.headers).toEqual([
+      { enabled: true, name: "X-Filter", value: "active" },
+      { enabled: true, name: "Cookie", value: "session=abc" },
+      { enabled: false, name: "Cookie", value: "debug=verbose" },
+    ]);
+  });
+
+  test("Preserves parameter cookies alongside cookie API-key authentication", async () => {
+    const imported = await convertOpenApi(
+      JSON.stringify({
+        openapi: "3.0.4",
+        info: { title: "Authenticated Cookie Test", version: "1.0.0" },
+        paths: {
+          "/items": {
+            get: {
+              security: [{ basicAuth: [], cookieKey: [] }],
+              parameters: [
+                {
+                  name: "session",
+                  in: "cookie",
+                  required: true,
+                  schema: { type: "string", example: "abc" },
+                },
+                {
+                  name: "debug",
+                  in: "cookie",
+                  schema: { type: "string", example: "verbose" },
+                },
+              ],
+              responses: {},
+            },
+          },
+        },
+        components: {
+          securitySchemes: {
+            basicAuth: { type: "http", scheme: "basic" },
+            cookieKey: { type: "apiKey", in: "cookie", name: "api_key" },
+          },
+        },
+      }),
+    );
+
+    expect(imported?.resources.httpRequests[0]).toEqual(
+      expect.objectContaining({
+        authenticationType: "basic",
+        headers: [
+          { enabled: true, name: "Cookie", value: "api_key=${[auth_cookie_key_key]}" },
+          { enabled: true, name: "Cookie", value: "session=abc" },
+          { enabled: false, name: "Cookie", value: "debug=verbose" },
+        ],
+      }),
+    );
+  });
+
+  test("Serializes structured query parameters according to style and explode", async () => {
+    const imported = await convertOpenApi(
+      JSON.stringify({
+        openapi: "3.0.4",
+        info: { title: "Serialization Test", version: "1.0.0" },
+        paths: {
+          "/items": {
+            get: {
+              parameters: [
+                {
+                  name: "filter",
+                  in: "query",
+                  required: true,
+                  style: "deepObject",
+                  explode: true,
+                  schema: {
+                    type: "object",
+                    properties: {
+                      role: { example: "admin" },
+                      active: { example: true },
+                    },
+                  },
+                },
+                {
+                  name: "tags",
+                  in: "query",
+                  style: "form",
+                  explode: true,
+                  schema: { type: "array", example: ["one", "two"] },
+                },
+              ],
+              responses: {},
+            },
+          },
+        },
+      }),
+    );
+
+    expect(imported?.resources.httpRequests[0]?.urlParameters).toEqual([
+      { enabled: true, name: "filter[role]", value: "admin" },
+      { enabled: true, name: "filter[active]", value: "true" },
+      { enabled: false, name: "tags", value: "one" },
+      { enabled: false, name: "tags", value: "two" },
+    ]);
+  });
+
+  test("Emits executable label and matrix path serializations", async () => {
+    const imported = await convertOpenApi(
+      JSON.stringify({
+        openapi: "3.0.4",
+        info: { title: "Path Serialization Test", version: "1.0.0" },
+        paths: {
+          "/labels/{labels}/matrix/{coordinates}/scalar/{color}/report.{format}": {
+            get: {
+              parameters: [
+                {
+                  name: "labels",
+                  in: "path",
+                  required: true,
+                  style: "label",
+                  explode: true,
+                  schema: { type: "array", example: ["one/two", "three"] },
+                },
+                {
+                  name: "coordinates",
+                  in: "path",
+                  required: true,
+                  style: "matrix",
+                  explode: true,
+                  schema: { type: "object", example: { x: "1;spoof=2", y: 2 } },
+                },
+                {
+                  name: "format",
+                  in: "path",
+                  required: true,
+                  schema: { type: "string", example: "json/evil" },
+                },
+                {
+                  name: "color",
+                  in: "path",
+                  required: true,
+                  style: "label",
+                  schema: { type: "string", example: "blue" },
+                },
+              ],
+              responses: {},
+            },
+          },
+        },
+      }),
+    );
+
+    expect(imported?.resources.httpRequests[0]).toEqual(
+      expect.objectContaining({
+        url: "${[baseUrl]}/labels/.one%2Ftwo.three/matrix/;x=1%3Bspoof%3D2;y=2/scalar/.blue/report.json%2Fevil",
+        urlParameters: [],
+      }),
+    );
+  });
+
   test("Prefers operation-level consumes for Swagger bodies", async () => {
     const imported = await convertOpenApi(
       JSON.stringify({