diff --git a/packages/insomnia-app/app/common/render.js b/packages/insomnia-app/app/common/render.js
index b1c66504f..ac14d51a0 100644
--- a/packages/insomnia-app/app/common/render.js
+++ b/packages/insomnia-app/app/common/render.js
@@ -291,6 +291,7 @@ export async function getRenderedRequestAndContext (
       settingEncodeUrl: renderedRequest.settingEncodeUrl,
       settingSendCookies: renderedRequest.settingSendCookies,
       settingStoreCookies: renderedRequest.settingStoreCookies,
+      settingRebuildPath: renderedRequest.settingRebuildPath,
       type: renderedRequest.type,
       url: renderedRequest.url
     }
diff --git a/packages/insomnia-app/app/models/request.js b/packages/insomnia-app/app/models/request.js
index e6a1994b3..a7feb01d1 100644
--- a/packages/insomnia-app/app/models/request.js
+++ b/packages/insomnia-app/app/models/request.js
@@ -61,7 +61,8 @@ type BaseRequest = {
   settingStoreCookies: boolean,
   settingSendCookies: boolean,
   settingDisableRenderRequestBody: boolean,
-  settingEncodeUrl: boolean
+  settingEncodeUrl: boolean,
+  settingRebuildPath: boolean
 };
 
 export type Request = BaseModel & BaseRequest;
@@ -83,7 +84,8 @@ export function init (): BaseRequest {
     settingStoreCookies: true,
     settingSendCookies: true,
     settingDisableRenderRequestBody: false,
-    settingEncodeUrl: true
+    settingEncodeUrl: true,
+    settingRebuildPath: true
   };
 }
 
diff --git a/packages/insomnia-app/app/network/network.js b/packages/insomnia-app/app/network/network.js
index 317b99556..bfe7da8ab 100644
--- a/packages/insomnia-app/app/network/network.js
+++ b/packages/insomnia-app/app/network/network.js
@@ -157,6 +157,11 @@ export async function _actuallySend (
         setOpt(Curl.option.MAXREDIRS, settings.maxRedirects);
       }
 
+      // Don't rebuild dot sequences in path
+      if (!renderedRequest.settingRebuildPath) {
+        setOpt(Curl.option.PATH_AS_IS, true);
+      }
+
       // Only set CURLOPT_CUSTOMREQUEST if not HEAD or GET. This is because Curl
       // See https://curl.haxx.se/libcurl/c/CURLOPT_CUSTOMREQUEST.html
       switch (renderedRequest.method.toUpperCase()) {
diff --git a/packages/insomnia-app/app/ui/components/modals/request-settings-modal.js b/packages/insomnia-app/app/ui/components/modals/request-settings-modal.js
index 6162b8ec9..16112cd18 100644
--- a/packages/insomnia-app/app/ui/components/modals/request-settings-modal.js
+++ b/packages/insomnia-app/app/ui/components/modals/request-settings-modal.js
@@ -162,6 +162,16 @@ class RequestSettingsModal extends PureComponent {
               </HelpTooltip>
             </label>
           </div>
+          <div className="form-control form-control--thin">
+            <label>Rebuild path dot sequences
+              <HelpTooltip position="top" className="space-left">
+                This instructs libcurl to squash sequences of "/../" or "/./" that may exist in
+                the URL's path part and that is supposed to be removed according to RFC 3986
+                section 5.2.4
+              </HelpTooltip>
+              {this.renderCheckboxInput('settingRebuildPath')}
+            </label>
+          </div>
         </div>
       </div>
     );
diff --git a/packages/insomnia-app/flow-typed/insomnia-libcurl.js b/packages/insomnia-app/flow-typed/insomnia-libcurl.js
index 6c1963523..b6c816f1e 100644
--- a/packages/insomnia-app/flow-typed/insomnia-libcurl.js
+++ b/packages/insomnia-app/flow-typed/insomnia-libcurl.js
@@ -25,6 +25,7 @@ declare class Curl {
     NOPROGRESS: number,
     NOPROXY: number,
     PASSWORD: number,
+    PATH_AS_IS: number,
     POST: number,
     POSTFIELDS: number,
     PROXY: number,