diff --git a/Riot/Modules/MatrixKit/Utils/MXKTools.m b/Riot/Modules/MatrixKit/Utils/MXKTools.m
index 3af8ef1fd..c993d0832 100644
--- a/Riot/Modules/MatrixKit/Utils/MXKTools.m
+++ b/Riot/Modules/MatrixKit/Utils/MXKTools.m
@@ -69,8 +69,9 @@ static NSRegularExpression* permalinkRegex;
         httpLinksRegex = [NSRegularExpression regularExpressionWithPattern:@"(?i)\\b(https?://\\S*)\\b" options:NSRegularExpressionCaseInsensitive error:nil];
         htmlTagsRegex  = [NSRegularExpression regularExpressionWithPattern:@"<(\\w+)[^>]*>" options:NSRegularExpressionCaseInsensitive error:nil];
         linkDetector = [NSDataDetector dataDetectorWithTypes:NSTextCheckingTypeLink error:nil];
-                
-        NSString *permalinkPattern = [NSString stringWithFormat:@"%@%@", BuildSettings.clientPermalinkBaseUrl ?: kMXMatrixDotToUrl, kMXKToolsRegexStringForPermalink];
+               
+        // if we have a custom clientPermalinkBaseUrl, we also need to support matrix.to permalinks
+        NSString *permalinkPattern = [NSString stringWithFormat:@"(?:%@|%@)%@", BuildSettings.clientPermalinkBaseUrl, kMXMatrixDotToUrl, kMXKToolsRegexStringForPermalink];
         permalinkRegex = [NSRegularExpression regularExpressionWithPattern:permalinkPattern options:NSRegularExpressionCaseInsensitive error:nil];
     });
 }
diff --git a/Riot/Modules/Pills/PillType.swift b/Riot/Modules/Pills/PillType.swift
index 8b90de15b..53b42e0e2 100644
--- a/Riot/Modules/Pills/PillType.swift
+++ b/Riot/Modules/Pills/PillType.swift
@@ -27,7 +27,7 @@ enum PillType: Codable {
 extension PillType {
     private static var regexPermalinkTarget: NSRegularExpression? = {
         let clientBaseUrl = BuildSettings.clientPermalinkBaseUrl ?? kMXMatrixDotToUrl
-        let pattern = #"\#(clientBaseUrl)/#/(?:(?:room|user)/)?((?:@|!|#)[^@!#/?\s]*)/?((?:\$)[^\$/?\s]*)?"#
+        let pattern = #"(?:\#(clientBaseUrl)|\#(kMXMatrixDotToUrl))/#/(?:(?:room|user)/)?((?:@|!|#)[^@!#/?\s]*)/?((?:\$)[^\$/?\s]*)?"#
         return try? NSRegularExpression(pattern: pattern, options: .caseInsensitive)
     }()
     
diff --git a/changelog.d/pr-7482.bugfix b/changelog.d/pr-7482.bugfix
new file mode 100644
index 000000000..842d621b2
--- /dev/null
+++ b/changelog.d/pr-7482.bugfix
@@ -0,0 +1 @@
+Continue to display pills for matrix.to permalinks if a custom permalinkBaseUrl is set.