diff --git a/src/main/certificateStore.ts b/src/main/certificateStore.ts
index 64c326b7..271ea700 100644
--- a/src/main/certificateStore.ts
+++ b/src/main/certificateStore.ts
@@ -13,10 +13,11 @@ import urlUtils from 'common/utils/url';
 
 import * as Validator from './Validator';
 
-function comparableCertificate(certificate: Certificate): ComparableCertificate {
+function comparableCertificate(certificate: Certificate, dontTrust = false): ComparableCertificate {
     return {
         data: certificate.data.toString(),
         issuerName: certificate.issuerName,
+        dontTrust,
     };
 }
 
@@ -53,8 +54,8 @@ export default class CertificateStore {
         fs.writeFileSync(this.storeFile, JSON.stringify(this.data, null, '  '));
     };
 
-    add = (targetURL: string, certificate: Certificate) => {
-        this.data[urlUtils.getHost(targetURL)] = comparableCertificate(certificate);
+    add = (targetURL: string, certificate: Certificate, dontTrust = false) => {
+        this.data[urlUtils.getHost(targetURL)] = comparableCertificate(certificate, dontTrust);
     };
 
     isExisting = (targetURL: string) => {
@@ -68,4 +69,12 @@ export default class CertificateStore {
         }
         return areEqual(this.data[host], comparableCertificate(certificate));
     };
+
+    isExplicitlyUntrusted = (targetURL: string) => {
+        // Whether or not the certificate was explicitly marked as untrusted by
+        // clicking "Don't ask again" checkbox before cancelling the connection.
+        const host = urlUtils.getHost(targetURL);
+        const dontTrust = this.data[host]?.dontTrust;
+        return dontTrust === undefined ? false : dontTrust;
+    }
 }
diff --git a/src/main/main.ts b/src/main/main.ts
index 9ac155eb..a8531b08 100644
--- a/src/main/main.ts
+++ b/src/main/main.ts
@@ -396,7 +396,11 @@ function handleAppCertificateError(event: electron.Event, webContents: electron.
         return;
     }
     const origin = parsedURL.origin;
-    if (certificateStore.isTrusted(origin, certificate)) {
+    if (certificateStore.isExplicitlyUntrusted(origin)) {
+        event.preventDefault();
+        log.warn(`Ignoring previously untrusted certificate for ${origin}`);
+        callback(false);
+    } else if (certificateStore.isTrusted(origin, certificate)) {
         event.preventDefault();
         callback(true);
     } else {
@@ -436,11 +440,13 @@ function handleAppCertificateError(event: electron.Event, webContents: electron.
                         type: 'error',
                         buttons: ['Trust Insecure Certificate', 'Cancel Connection'],
                         cancelId: 1,
+                        checkboxChecked: false,
+                        checkboxLabel: "Don't ask again",
                     });
                 }
-                return {response};
+                return {response, checkboxChecked: false};
             }).then(
-            ({response: responseTwo}) => {
+            ({response: responseTwo, checkboxChecked}) => {
                 if (responseTwo === 0) {
                     certificateStore.add(origin, certificate);
                     certificateStore.save();
@@ -448,6 +454,10 @@ function handleAppCertificateError(event: electron.Event, webContents: electron.
                     certificateErrorCallbacks.delete(errorID);
                     webContents.loadURL(url);
                 } else {
+                    if (checkboxChecked) {
+                        certificateStore.add(origin, certificate, true);
+                        certificateStore.save();
+                    }
                     certificateErrorCallbacks.get(errorID)(false);
                     certificateErrorCallbacks.delete(errorID);
                 }
diff --git a/src/types/certificate.ts b/src/types/certificate.ts
index 65462da4..5edb3240 100644
--- a/src/types/certificate.ts
+++ b/src/types/certificate.ts
@@ -6,6 +6,7 @@ import {Certificate} from 'electron/common';
 export type ComparableCertificate = {
     data: string;
     issuerName: string;
+    dontTrust: boolean;
 }
 
 export type CertificateModalData = {