diff --git a/apps/settings/lib/Controller/CheckSetupController.php b/apps/settings/lib/Controller/CheckSetupController.php
index 1429fd5ed8..04711cf530 100644
--- a/apps/settings/lib/Controller/CheckSetupController.php
+++ b/apps/settings/lib/Controller/CheckSetupController.php
@@ -703,6 +703,7 @@ Raw output
 				'pendingBigIntConversionColumns' => $this->hasBigIntConversionPendingColumns(),
 				'isMysqlUsedWithoutUTF8MB4' => $this->isMysqlUsedWithoutUTF8MB4(),
 				'isEnoughTempSpaceAvailableIfS3PrimaryStorageIsUsed' => $this->isEnoughTempSpaceAvailableIfS3PrimaryStorageIsUsed(),
+				'reverseProxyGeneratedURL' => $this->urlGenerator->getAbsoluteURL('index.php'),
 			]
 		);
 	}
diff --git a/apps/settings/tests/Controller/CheckSetupControllerTest.php b/apps/settings/tests/Controller/CheckSetupControllerTest.php
index 7740b2f427..93c7814389 100644
--- a/apps/settings/tests/Controller/CheckSetupControllerTest.php
+++ b/apps/settings/tests/Controller/CheckSetupControllerTest.php
@@ -426,14 +426,6 @@ class CheckSetupControllerTest extends TestCase {
 		$this->clientService->expects($this->exactly(4))
 			->method('newClient')
 			->will($this->returnValue($client));
-		$this->urlGenerator->expects($this->at(0))
-			->method('linkToDocs')
-			->with('admin-performance')
-			->willReturn('http://docs.example.org/server/go.php?to=admin-performance');
-		$this->urlGenerator->expects($this->at(1))
-			->method('linkToDocs')
-			->with('admin-security')
-			->willReturn('https://docs.example.org/server/8.1/admin_manual/configuration_server/hardening.html');
 		$this->checkSetupController
 			->expects($this->once())
 			->method('isPhpOutdated')
@@ -442,26 +434,6 @@ class CheckSetupControllerTest extends TestCase {
 			->expects($this->once())
 			->method('isOpcacheProperlySetup')
 			->willReturn(false);
-		$this->urlGenerator->expects($this->at(2))
-			->method('linkToDocs')
-			->with('admin-reverse-proxy')
-			->willReturn('reverse-proxy-doc-link');
-		$this->urlGenerator->expects($this->at(3))
-			->method('linkToDocs')
-			->with('admin-code-integrity')
-			->willReturn('http://docs.example.org/server/go.php?to=admin-code-integrity');
-		$this->urlGenerator->expects($this->at(4))
-			->method('linkToDocs')
-			->with('admin-php-opcache')
-			->willReturn('http://docs.example.org/server/go.php?to=admin-php-opcache');
-		$this->urlGenerator->expects($this->at(5))
-			->method('linkToDocs')
-			->with('admin-db-conversion')
-			->willReturn('http://docs.example.org/server/go.php?to=admin-db-conversion');
-		$this->urlGenerator->expects($this->at(6))
-			->method('getAbsoluteURL')
-			->with('index.php/settings/admin')
-			->willReturn('https://server/index.php/settings/admin');
 		$this->checkSetupController
 			->method('hasFreeTypeSupport')
 			->willReturn(false);
@@ -540,6 +512,40 @@ class CheckSetupControllerTest extends TestCase {
 			->method('isEnoughTempSpaceAvailableIfS3PrimaryStorageIsUsed')
 			->willReturn(true);
 
+		$this->urlGenerator->method('linkToDocs')
+			->willReturnCallback(function(string $key): string {
+				if ($key === 'admin-performance') {
+					return 'http://docs.example.org/server/go.php?to=admin-performance';
+				}
+				if ($key === 'admin-security') {
+					return 'https://docs.example.org/server/8.1/admin_manual/configuration_server/hardening.html';
+				}
+				if ($key === 'admin-reverse-proxy') {
+					return 'reverse-proxy-doc-link';
+				}
+				if ($key === 'admin-code-integrity') {
+					return 'http://docs.example.org/server/go.php?to=admin-code-integrity';
+				}
+				if ($key === 'admin-php-opcache') {
+					return 'http://docs.example.org/server/go.php?to=admin-php-opcache';
+				}
+				if ($key === 'admin-db-conversion') {
+					return 'http://docs.example.org/server/go.php?to=admin-db-conversion';
+				}
+				return '';
+			});
+
+		$this->urlGenerator->method('getAbsoluteURL')
+			->willReturnCallback(function(string $url): string {
+				if ($url === 'index.php/settings/admin') {
+					return 'https://server/index.php/settings/admin';
+				}
+				if ($url === 'index.php') {
+					return 'https://server/index.php';
+				}
+				return '';
+			});
+
 		$expected = new DataResponse(
 			[
 				'isGetenvServerWorking' => true,
@@ -585,6 +591,7 @@ class CheckSetupControllerTest extends TestCase {
 				'pendingBigIntConversionColumns' => [],
 				'isMysqlUsedWithoutUTF8MB4' => false,
 				'isEnoughTempSpaceAvailableIfS3PrimaryStorageIsUsed' => true,
+				'reverseProxyGeneratedURL' => 'https://server/index.php',
 			]
 		);
 		$this->assertEquals($expected, $this->checkSetupController->check());
diff --git a/core/js/setupchecks.js b/core/js/setupchecks.js
index 33ba31f049..12d1104a63 100644
--- a/core/js/setupchecks.js
+++ b/core/js/setupchecks.js
@@ -460,6 +460,18 @@
 							type: OC.SetupChecks.MESSAGE_TYPE_WARNING
 						})
 					}
+					if (window.location.protocol === 'http:' && data.reverseProxyGeneratedURL.split('/')[0] !== 'https:') {
+						messages.push({
+							msg: t(
+								'core',
+								'You are accessing your instance over a secure connection, however your instance is generating insecure URLs. This most likely means that you are behind a reverse proxy and the overwrite config variables are not set correctly. Please read <a target="_blank" rel="noreferrer noopener" href="{docLink}">the documentation page about this</a>.',
+								{
+									docLink: data.reverseProxyDocs
+								}
+							),
+							type: OC.SetupChecks.MESSAGE_TYPE_WARNING
+						})
+					}
 
 				} else {
 					messages.push({
diff --git a/core/js/tests/specs/setupchecksSpec.js b/core/js/tests/specs/setupchecksSpec.js
index 86d4e47a81..5e93cbf7bd 100644
--- a/core/js/tests/specs/setupchecksSpec.js
+++ b/core/js/tests/specs/setupchecksSpec.js
@@ -249,7 +249,8 @@ describe('OC.SetupChecks tests', function() {
 					recommendedPHPModules: [],
 					pendingBigIntConversionColumns: [],
 					isMysqlUsedWithoutUTF8MB4: false,
-					isEnoughTempSpaceAvailableIfS3PrimaryStorageIsUsed: true
+					isEnoughTempSpaceAvailableIfS3PrimaryStorageIsUsed: true,
+					reverseProxyGeneratedURL: 'https://server',
 				})
 			);
 
@@ -301,7 +302,8 @@ describe('OC.SetupChecks tests', function() {
 					recommendedPHPModules: [],
 					pendingBigIntConversionColumns: [],
 					isMysqlUsedWithoutUTF8MB4: false,
-					isEnoughTempSpaceAvailableIfS3PrimaryStorageIsUsed: true
+					isEnoughTempSpaceAvailableIfS3PrimaryStorageIsUsed: true,
+					reverseProxyGeneratedURL: 'https://server',
 				})
 			);
 
@@ -354,7 +356,8 @@ describe('OC.SetupChecks tests', function() {
 					recommendedPHPModules: [],
 					pendingBigIntConversionColumns: [],
 					isMysqlUsedWithoutUTF8MB4: false,
-					isEnoughTempSpaceAvailableIfS3PrimaryStorageIsUsed: true
+					isEnoughTempSpaceAvailableIfS3PrimaryStorageIsUsed: true,
+					reverseProxyGeneratedURL: 'https://server',
 				})
 			);
 
@@ -405,7 +408,8 @@ describe('OC.SetupChecks tests', function() {
 					recommendedPHPModules: [],
 					pendingBigIntConversionColumns: [],
 					isMysqlUsedWithoutUTF8MB4: false,
-					isEnoughTempSpaceAvailableIfS3PrimaryStorageIsUsed: true
+					isEnoughTempSpaceAvailableIfS3PrimaryStorageIsUsed: true,
+					reverseProxyGeneratedURL: 'https://server',
 				})
 			);
 
@@ -454,7 +458,8 @@ describe('OC.SetupChecks tests', function() {
 					recommendedPHPModules: [],
 					pendingBigIntConversionColumns: [],
 					isMysqlUsedWithoutUTF8MB4: false,
-					isEnoughTempSpaceAvailableIfS3PrimaryStorageIsUsed: true
+					isEnoughTempSpaceAvailableIfS3PrimaryStorageIsUsed: true,
+					reverseProxyGeneratedURL: 'https://server',
 				})
 			);
 
@@ -505,7 +510,8 @@ describe('OC.SetupChecks tests', function() {
 					recommendedPHPModules: [],
 					pendingBigIntConversionColumns: [],
 					isMysqlUsedWithoutUTF8MB4: false,
-					isEnoughTempSpaceAvailableIfS3PrimaryStorageIsUsed: true
+					isEnoughTempSpaceAvailableIfS3PrimaryStorageIsUsed: true,
+					reverseProxyGeneratedURL: 'https://server',
 				})
 			);
 
@@ -554,7 +560,8 @@ describe('OC.SetupChecks tests', function() {
 					recommendedPHPModules: [],
 					pendingBigIntConversionColumns: [],
 					isMysqlUsedWithoutUTF8MB4: false,
-					isEnoughTempSpaceAvailableIfS3PrimaryStorageIsUsed: true
+					isEnoughTempSpaceAvailableIfS3PrimaryStorageIsUsed: true,
+					reverseProxyGeneratedURL: 'https://server',
 				})
 			);
 
@@ -603,7 +610,8 @@ describe('OC.SetupChecks tests', function() {
 					recommendedPHPModules: [],
 					pendingBigIntConversionColumns: [],
 					isMysqlUsedWithoutUTF8MB4: false,
-					isEnoughTempSpaceAvailableIfS3PrimaryStorageIsUsed: true
+					isEnoughTempSpaceAvailableIfS3PrimaryStorageIsUsed: true,
+					reverseProxyGeneratedURL: 'https://server',
 				})
 			);
 
@@ -652,7 +660,8 @@ describe('OC.SetupChecks tests', function() {
 					recommendedPHPModules: [],
 					pendingBigIntConversionColumns: [],
 					isMysqlUsedWithoutUTF8MB4: false,
-					isEnoughTempSpaceAvailableIfS3PrimaryStorageIsUsed: true
+					isEnoughTempSpaceAvailableIfS3PrimaryStorageIsUsed: true,
+					reverseProxyGeneratedURL: 'https://server',
 				})
 			);
 
@@ -722,7 +731,8 @@ describe('OC.SetupChecks tests', function() {
 					recommendedPHPModules: [],
 					pendingBigIntConversionColumns: [],
 					isMysqlUsedWithoutUTF8MB4: false,
-					isEnoughTempSpaceAvailableIfS3PrimaryStorageIsUsed: true
+					isEnoughTempSpaceAvailableIfS3PrimaryStorageIsUsed: true,
+					reverseProxyGeneratedURL: 'https://server',
 				})
 			);
 
@@ -772,7 +782,8 @@ describe('OC.SetupChecks tests', function() {
 					recommendedPHPModules: [],
 					pendingBigIntConversionColumns: [],
 					isMysqlUsedWithoutUTF8MB4: false,
-					isEnoughTempSpaceAvailableIfS3PrimaryStorageIsUsed: true
+					isEnoughTempSpaceAvailableIfS3PrimaryStorageIsUsed: true,
+					reverseProxyGeneratedURL: 'https://server',
 				})
 			);
 
@@ -822,7 +833,8 @@ describe('OC.SetupChecks tests', function() {
 					recommendedPHPModules: [],
 					pendingBigIntConversionColumns: [],
 					isMysqlUsedWithoutUTF8MB4: false,
-					isEnoughTempSpaceAvailableIfS3PrimaryStorageIsUsed: true
+					isEnoughTempSpaceAvailableIfS3PrimaryStorageIsUsed: true,
+					reverseProxyGeneratedURL: 'https://server',
 				})
 			);
 
@@ -872,7 +884,8 @@ describe('OC.SetupChecks tests', function() {
 					recommendedPHPModules: [],
 					pendingBigIntConversionColumns: [],
 					isMysqlUsedWithoutUTF8MB4: false,
-					isEnoughTempSpaceAvailableIfS3PrimaryStorageIsUsed: true
+					isEnoughTempSpaceAvailableIfS3PrimaryStorageIsUsed: true,
+					reverseProxyGeneratedURL: 'https://server',
 				})
 			);
 
@@ -921,7 +934,8 @@ describe('OC.SetupChecks tests', function() {
 					recommendedPHPModules: [],
 					pendingBigIntConversionColumns: [],
 					isMysqlUsedWithoutUTF8MB4: true,
-					isEnoughTempSpaceAvailableIfS3PrimaryStorageIsUsed: true
+					isEnoughTempSpaceAvailableIfS3PrimaryStorageIsUsed: true,
+					reverseProxyGeneratedURL: 'https://server',
 				})
 			);
 
@@ -934,6 +948,57 @@ describe('OC.SetupChecks tests', function() {
 			});
 		});
 
+		it('should return an error if the protocol is https but the server generates http links', function(done) {
+			var async = OC.SetupChecks.checkSetup();
+
+			suite.server.requests[0].respond(
+				200,
+				{
+					'Content-Type': 'application/json',
+				},
+				JSON.stringify({
+					hasFileinfoInstalled: true,
+					isGetenvServerWorking: true,
+					isReadOnlyConfig: false,
+					hasWorkingFileLocking: true,
+					hasValidTransactionIsolationLevel: true,
+					suggestedOverwriteCliURL: '',
+					isRandomnessSecure: true,
+					securityDocs: 'https://docs.owncloud.org/myDocs.html',
+					serverHasInternetConnectionProblems: false,
+					isMemcacheConfigured: true,
+					forwardedForHeadersWorking: true,
+					isCorrectMemcachedPHPModuleInstalled: true,
+					hasPassedCodeIntegrityCheck: true,
+					isOpcacheProperlySetup: true,
+					hasOpcacheLoaded: true,
+					isSettimelimitAvailable: true,
+					hasFreeTypeSupport: true,
+					missingIndexes: [],
+					cronErrors: [],
+					cronInfo: {
+						diffInSeconds: 0
+					},
+					isMemoryLimitSufficient: true,
+					appDirsWithDifferentOwner: [],
+					recommendedPHPModules: [],
+					pendingBigIntConversionColumns: [],
+					isMysqlUsedWithoutUTF8MB4: false,
+					isEnoughTempSpaceAvailableIfS3PrimaryStorageIsUsed: true,
+					reverseProxyDocs: 'https://docs.nextcloud.com/foo/bar.html',
+					reverseProxyGeneratedURL: 'http://server',
+				})
+			);
+
+			async.done(function( data, s, x ){
+				expect(data).toEqual([{
+					msg: 'You are accessing your instance over a secure connection, however your instance is generating insecure URLs. This most likely means that you are behind a reverse proxy and the overwrite config variables are not set correctly. Please read <a href="https://docs.nextcloud.com/foo/bar.html" rel="noreferrer noopener">the documentation page about this</a>.',
+					type: OC.SetupChecks.MESSAGE_TYPE_WARNING
+				}]);
+				done();
+			});
+		});
+
 		it('should return an error if there is not enough free space in the temp directory', function(done) {
 			var async = OC.SetupChecks.checkSetup();
 
@@ -970,7 +1035,8 @@ describe('OC.SetupChecks tests', function() {
 					recommendedPHPModules: [],
 					pendingBigIntConversionColumns: [],
 					isMysqlUsedWithoutUTF8MB4: false,
-					isEnoughTempSpaceAvailableIfS3PrimaryStorageIsUsed: false
+					isEnoughTempSpaceAvailableIfS3PrimaryStorageIsUsed: false,
+					reverseProxyGeneratedURL: 'https://server',
 				})
 			);