diff --git a/compiler/src/dotty/tools/dotc/typer/Typer.scala b/compiler/src/dotty/tools/dotc/typer/Typer.scala
index 571d90181d18..88576ede9eda 100644
--- a/compiler/src/dotty/tools/dotc/typer/Typer.scala
+++ b/compiler/src/dotty/tools/dotc/typer/Typer.scala
@@ -3483,28 +3483,41 @@ class Typer extends Namer
       }
 
       // try an extension method in scope
-      pt match {
+      pt match
         case selProto @ SelectionProto(selName: TermName, mbrType, _, _) =>
+          val origCtx = ctx
           def tryExtension(using Context): Tree =
+            var tried: untpd.Tree = untpd.EmptyTree
             try
               findRef(selName, WildcardType, ExtensionMethod, tree.srcPos) match
                 case ref: TermRef =>
-                  extMethodApply(untpd.ref(ref).withSpan(tree.span), tree, mbrType)
+                  tried = untpd.ref(ref).withSpan(tree.span)
+                  extMethodApply(tried, tree, mbrType)
                 case _ => findRef(selProto.extensionName, WildcardType, ExtensionMethod, tree.srcPos) match
                   case ref: TermRef =>
-                    extMethodApply(untpd.ref(ref).withSpan(tree.span), tree, mbrType)
+                    tried = untpd.ref(ref).withSpan(tree.span)
+                    extMethodApply(tried, tree, mbrType)
                   case _ => EmptyTree
-            catch case ex: TypeError => errorTree(tree, ex, tree.srcPos)
+            catch case ex: TypeError =>
+              ex match
+                case ex: CyclicReference if ex.denot.is(Extension) && ex.denot.name == selName =>
+                  report.error(
+                    em"""An extension method for `.$selName` was tried but could not be fully constructed
+                        |since there was a cyclic reference involving ${ex.denot.symbol.showLocated}""",
+                    tree.srcPos)(using origCtx)
+                case _ =>
+              if tried.isEmpty then EmptyTree
+              else errorTree(tried, ex, tree.srcPos)
+
           val nestedCtx = ctx.fresh.setNewTyperState()
-          val app = tryExtension(using nestedCtx)
-          if (!app.isEmpty && !nestedCtx.reporter.hasErrors) {
+          val tried = tryExtension(using nestedCtx)
+          if !tried.isEmpty && !nestedCtx.reporter.hasErrors then
             nestedCtx.typerState.commit()
-            return ExtMethodApply(app)
-          }
-          else if !app.isEmpty then
-            rememberSearchFailure(tree, SearchFailure(app.withType(FailedExtension(app, pt))))
+            return ExtMethodApply(tried)
+          else if !tried.isEmpty then
+            rememberSearchFailure(tree,
+              SearchFailure(tried.withType(FailedExtension(tried, pt))))
         case _ =>
-      }
 
       // try an implicit conversion
       val prevConstraint = ctx.typerState.constraint
diff --git a/scala3doc/src/dotty/dokka/tasty/BasicSupport.scala b/scala3doc/src/dotty/dokka/tasty/BasicSupport.scala
index e49244678e44..08b1cfa2ee66 100644
--- a/scala3doc/src/dotty/dokka/tasty/BasicSupport.scala
+++ b/scala3doc/src/dotty/dokka/tasty/BasicSupport.scala
@@ -5,6 +5,7 @@ import org.jetbrains.dokka.model._
 import collection.JavaConverters._
 import dotty.dokka._
 import dotty.dokka.model.api.Annotation
+import doc.DocumentationNode
 import dotty.dokka.model.api.TastyDocumentableSource
 
 trait BasicSupport:
@@ -34,10 +35,11 @@ trait BasicSupport:
 
 
   extension (sym: Symbol):
-    def documentation(using cxt: Context) = sym.documentation match
-      case Some(comment) =>
+    def documentation(using cxt: Context): Map[SourceSetWrapper, DocumentationNode] =
+      qctx.reflect.SymbolMethods.documentation(sym) match
+        case Some(comment) =>
           Map(sourceSet -> parseComment(comment, sym.tree))
-      case None =>
+        case None =>
           Map.empty
 
     def source(using ctx: Context) =
diff --git a/tests/neg/i7986.check b/tests/neg/i7986.check
new file mode 100644
index 000000000000..042182324634
--- /dev/null
+++ b/tests/neg/i7986.check
@@ -0,0 +1,5 @@
+-- Error: tests/neg/i7986.scala:3:56 -----------------------------------------------------------------------------------
+3 |extension (project: Project) def dependencies = project.name.dependencies // error, following a cyclic reference warning
+  |                                                ^^^^^^^^^^^^
+  |                              An extension method for `.dependencies` was tried but could not be fully constructed
+  |                              since there was a cyclic reference involving method dependencies
diff --git a/tests/neg/i7986.scala b/tests/neg/i7986.scala
new file mode 100644
index 000000000000..61c896c4e145
--- /dev/null
+++ b/tests/neg/i7986.scala
@@ -0,0 +1,3 @@
+case class Project(name: String)
+extension (name: String) def dependencies = ???
+extension (project: Project) def dependencies = project.name.dependencies // error, following a cyclic reference warning
\ No newline at end of file
diff --git a/tests/pos/i7986.scala b/tests/pos/i7986.scala
new file mode 100644
index 000000000000..335ff51f5649
--- /dev/null
+++ b/tests/pos/i7986.scala
@@ -0,0 +1,3 @@
+case class Project(name: String)
+extension (name: String) def dependencies: String = ???
+extension (project: Project) def dependencies: String = project.name.dependencies
diff --git a/tests/pos/i8256.scala b/tests/pos/i8256.scala
index ecccc21c639b..bb084cc373d8 100644
--- a/tests/pos/i8256.scala
+++ b/tests/pos/i8256.scala
@@ -7,4 +7,4 @@ val a = 1
 
   val fetch = implicitly[Test[1]]
 
-@main def main() : Unit = {}
\ No newline at end of file
+@main def test() : Unit = {}
\ No newline at end of file