diff --git a/libsolidity/interface/FileReader.cpp b/libsolidity/interface/FileReader.cpp
index adb4b01ca..e581c4a56 100644
--- a/libsolidity/interface/FileReader.cpp
+++ b/libsolidity/interface/FileReader.cpp
@@ -116,7 +116,6 @@ ReadCallback::Result FileReader::readFile(string const& _kind, string const& _so
 		for (auto const& prefix: prefixes)
 		{
 			boost::filesystem::path canonicalPath = normalizeCLIPathForVFS(prefix / strippedSourceUnitName, SymlinkResolution::Enabled);
-
 			if (boost::filesystem::exists(canonicalPath))
 				candidates.push_back(std::move(canonicalPath));
 		}
@@ -124,7 +123,12 @@ ReadCallback::Result FileReader::readFile(string const& _kind, string const& _so
 		auto pathToQuotedString = [](boost::filesystem::path const& _path){ return "\"" + _path.string() + "\""; };
 
 		if (candidates.empty())
-			return ReadCallback::Result{false, "File not found."};
+			return ReadCallback::Result{
+				false,
+				"File not found. Searched the following locations: " +
+				joinHumanReadable(prefixes | ranges::views::transform(pathToQuotedString), ", ") +
+				"."
+			};
 
 		if (candidates.size() >= 2)
 			return ReadCallback::Result{
@@ -135,11 +139,13 @@ ReadCallback::Result FileReader::readFile(string const& _kind, string const& _so
 				"."
 			};
 
-		FileSystemPathSet extraAllowedPaths = {m_basePath.empty() ? "." : m_basePath};
-		extraAllowedPaths += m_includePaths;
+		FileSystemPathSet allowedPaths =
+			m_allowedDirectories +
+			decltype(allowedPaths){m_basePath.empty() ? "." : m_basePath} +
+			m_includePaths;
 
 		bool isAllowed = false;
-		for (boost::filesystem::path const& allowedDir: m_allowedDirectories + extraAllowedPaths)
+		for (boost::filesystem::path const& allowedDir: allowedPaths)
 			if (isPathPrefix(normalizeCLIPathForVFS(allowedDir, SymlinkResolution::Enabled), candidates[0]))
 			{
 				isAllowed = true;
@@ -147,7 +153,12 @@ ReadCallback::Result FileReader::readFile(string const& _kind, string const& _so
 			}
 
 		if (!isAllowed)
-			return ReadCallback::Result{false, "File outside of allowed directories."};
+			return ReadCallback::Result{
+				false,
+				"File outside of allowed directories. The following are allowed: " +
+				joinHumanReadable(allowedPaths | ranges::views::transform(pathToQuotedString), ", ") +
+				"."
+			};
 
 		if (!boost::filesystem::is_regular_file(candidates[0]))
 			return ReadCallback::Result{false, "Not a valid file."};
diff --git a/test/cmdlineTests/standard_yul_single_file_via_urls/output.json b/test/cmdlineTests/standard_yul_single_file_via_urls/output.json
index 3f62fa0fe..a97057c88 100644
--- a/test/cmdlineTests/standard_yul_single_file_via_urls/output.json
+++ b/test/cmdlineTests/standard_yul_single_file_via_urls/output.json
@@ -3,8 +3,8 @@
     [
         {
             "component": "general",
-            "formattedMessage": "Cannot import url (\"in.yul\"): File not found.",
-            "message": "Cannot import url (\"in.yul\"): File not found.",
+            "formattedMessage": "Cannot import url (\"in.yul\"): File not found. Searched the following locations: \"\".",
+            "message": "Cannot import url (\"in.yul\"): File not found. Searched the following locations: \"\".",
             "severity": "error",
             "type": "IOError"
         },
diff --git a/test/solc/CommandLineInterfaceAllowPaths.cpp b/test/solc/CommandLineInterfaceAllowPaths.cpp
index 77f727014..472f2184b 100644
--- a/test/solc/CommandLineInterfaceAllowPaths.cpp
+++ b/test/solc/CommandLineInterfaceAllowPaths.cpp
@@ -100,7 +100,7 @@ ImportCheck checkImport(
 		return ImportCheck::OK();
 
 	static regex const sourceNotFoundErrorRegex{
-		R"(^Error \(6275\): Source ".+" not found: (.*)\.\n)"
+		R"(^Error \(6275\): Source "[^"]+" not found: (.*)\.\n)"
 		R"(\s*--> .*<stdin>:\d+:\d+:\n)"
 		R"(\s*\|\n)"
 		R"(\d+\s*\| import '.+';\n)"
@@ -110,12 +110,12 @@ ImportCheck checkImport(
 	smatch submatches;
 	if (!regex_match(cliResult.stderrContent, submatches, sourceNotFoundErrorRegex))
 		return ImportCheck::Unknown("Unexpected stderr content: '" + cliResult.stderrContent + "'");
-	if (submatches[1] != "File not found" && submatches[1] != "File outside of allowed directories")
+	if (submatches[1] != "File not found" && !boost::starts_with(string(submatches[1]), "File outside of allowed directories"))
 		return ImportCheck::Unknown("Unexpected error message: '" + cliResult.stderrContent + "'");
 
 	if (submatches[1] == "File not found")
 		return ImportCheck::FileNotFound();
-	else if (submatches[1] == "File outside of allowed directories")
+	else if (boost::starts_with(string(submatches[1]), "File outside of allowed directories"))
 		return ImportCheck::PathDisallowed();
 	else
 		return ImportCheck::Unknown("Unexpected error message '" + submatches[1].str() + "'");