diff --git a/Sources/DocCDocumentation/DoccDocumentationError.swift b/Sources/DocCDocumentation/DoccDocumentationError.swift
index 35c00b9a4..263fbea81 100644
--- a/Sources/DocCDocumentation/DoccDocumentationError.swift
+++ b/Sources/DocCDocumentation/DoccDocumentationError.swift
@@ -14,14 +14,17 @@ import Foundation
 package import LanguageServerProtocol
 
 package enum DocCDocumentationError: LocalizedError {
-  case noDocumentation
+  case unsupportedLanguage(Language)
+  case noDocumentableSymbols
   case indexNotAvailable
   case symbolNotFound(String)
 
   var errorDescription: String? {
     switch self {
-    case .noDocumentation:
-      return "No documentation could be rendered for the position in this document"
+    case .unsupportedLanguage(let language):
+      return "Documentation preview is not available for \(language.description) files"
+    case .noDocumentableSymbols:
+      return "No documentable symbols were found in this Swift file"
     case .indexNotAvailable:
       return "The index is not availble to complete the request"
     case .symbolNotFound(let symbolName):
diff --git a/Sources/SourceKitLSP/Clang/ClangLanguageService.swift b/Sources/SourceKitLSP/Clang/ClangLanguageService.swift
index 6b75bc788..e10eb9eea 100644
--- a/Sources/SourceKitLSP/Clang/ClangLanguageService.swift
+++ b/Sources/SourceKitLSP/Clang/ClangLanguageService.swift
@@ -495,7 +495,12 @@ extension ClangLanguageService {
 
   #if canImport(DocCDocumentation)
   func doccDocumentation(_ req: DoccDocumentationRequest) async throws -> DoccDocumentationResponse {
-    throw ResponseError.requestFailed(doccDocumentationError: .noDocumentation)
+    guard let sourceKitLSPServer else {
+      throw ResponseError.unknown("Connection to the editor closed")
+    }
+
+    let snapshot = try sourceKitLSPServer.documentManager.latestSnapshot(req.textDocument.uri)
+    throw ResponseError.requestFailed(doccDocumentationError: .unsupportedLanguage(snapshot.language))
   }
   #endif
 
diff --git a/Sources/SourceKitLSP/Documentation/DoccDocumentationHandler.swift b/Sources/SourceKitLSP/Documentation/DoccDocumentationHandler.swift
index 332a335fe..078d13dae 100644
--- a/Sources/SourceKitLSP/Documentation/DoccDocumentationHandler.swift
+++ b/Sources/SourceKitLSP/Documentation/DoccDocumentationHandler.swift
@@ -105,7 +105,7 @@ extension DocumentationLanguageService {
         catalogURL: catalogURL
       )
     default:
-      throw ResponseError.requestFailed(doccDocumentationError: .noDocumentation)
+      throw ResponseError.requestFailed(doccDocumentationError: .unsupportedLanguage(snapshot.language))
     }
   }
 }
diff --git a/Sources/SourceKitLSP/Swift/DoccDocumentation.swift b/Sources/SourceKitLSP/Swift/DoccDocumentation.swift
index d57fde7cc..728fe73f5 100644
--- a/Sources/SourceKitLSP/Swift/DoccDocumentation.swift
+++ b/Sources/SourceKitLSP/Swift/DoccDocumentation.swift
@@ -48,7 +48,7 @@ extension SwiftLanguageService {
         position: snapshot.absolutePosition(of: position)
       )
     else {
-      throw ResponseError.requestFailed(doccDocumentationError: .noDocumentation)
+      throw ResponseError.requestFailed(doccDocumentationError: .noDocumentableSymbols)
     }
     // Retrieve the symbol graph as well as information about the symbol
     let symbolPosition = await adjustPositionToStartOfIdentifier(
@@ -130,30 +130,67 @@ fileprivate struct DocumentableSymbol {
     }
   }
 
+  init?(node: any SyntaxProtocol) {
+    if let namedDecl = node.asProtocol(NamedDeclSyntax.self) {
+      self = DocumentableSymbol(node: namedDecl, position: namedDecl.name.positionAfterSkippingLeadingTrivia)
+    } else if let initDecl = node.as(InitializerDeclSyntax.self) {
+      self = DocumentableSymbol(node: initDecl, position: initDecl.initKeyword.positionAfterSkippingLeadingTrivia)
+    } else if let deinitDecl = node.as(DeinitializerDeclSyntax.self) {
+      self = DocumentableSymbol(node: deinitDecl, position: deinitDecl.deinitKeyword.positionAfterSkippingLeadingTrivia)
+    } else if let functionDecl = node.as(FunctionDeclSyntax.self) {
+      self = DocumentableSymbol(node: functionDecl, position: functionDecl.name.positionAfterSkippingLeadingTrivia)
+    } else if let subscriptDecl = node.as(SubscriptDeclSyntax.self) {
+      self = DocumentableSymbol(node: subscriptDecl, position: subscriptDecl.positionAfterSkippingLeadingTrivia)
+    } else if let variableDecl = node.as(VariableDeclSyntax.self) {
+      guard let identifier = variableDecl.bindings.only?.pattern.as(IdentifierPatternSyntax.self) else {
+        return nil
+      }
+      self = DocumentableSymbol(node: variableDecl, position: identifier.positionAfterSkippingLeadingTrivia)
+    } else if let enumCaseDecl = node.as(EnumCaseDeclSyntax.self) {
+      guard let name = enumCaseDecl.elements.only?.name else {
+        return nil
+      }
+      self = DocumentableSymbol(node: enumCaseDecl, position: name.positionAfterSkippingLeadingTrivia)
+    } else {
+      return nil
+    }
+  }
+
   static func findNearestSymbol(syntaxTree: SourceFileSyntax, position: AbsolutePosition) -> DocumentableSymbol? {
-    guard let token = syntaxTree.token(at: position) else {
+    let token: TokenSyntax
+    if let tokenAtPosition = syntaxTree.token(at: position) {
+      token = tokenAtPosition
+    } else if position >= syntaxTree.endPosition, let lastToken = syntaxTree.lastToken(viewMode: .sourceAccurate) {
+      // token(at:) returns nil if position is at the end of the document.
+      token = lastToken
+    } else if position < syntaxTree.position, let firstToken = syntaxTree.firstToken(viewMode: .sourceAccurate) {
+      // No case in practice where this happens but good to cover anyway
+      token = firstToken
+    } else {
       return nil
     }
-    return token.ancestorOrSelf { node in
-      if let namedDecl = node.asProtocol(NamedDeclSyntax.self) {
-        return DocumentableSymbol(node: namedDecl, position: namedDecl.name.positionAfterSkippingLeadingTrivia)
-      } else if let initDecl = node.as(InitializerDeclSyntax.self) {
-        return DocumentableSymbol(node: initDecl, position: initDecl.initKeyword.positionAfterSkippingLeadingTrivia)
-      } else if let functionDecl = node.as(FunctionDeclSyntax.self) {
-        return DocumentableSymbol(node: functionDecl, position: functionDecl.name.positionAfterSkippingLeadingTrivia)
-      } else if let variableDecl = node.as(VariableDeclSyntax.self) {
-        guard let identifier = variableDecl.bindings.only?.pattern.as(IdentifierPatternSyntax.self) else {
-          return nil
-        }
-        return DocumentableSymbol(node: variableDecl, position: identifier.positionAfterSkippingLeadingTrivia)
-      } else if let enumCaseDecl = node.as(EnumCaseDeclSyntax.self) {
-        guard let name = enumCaseDecl.elements.only?.name else {
-          return nil
-        }
-        return DocumentableSymbol(node: enumCaseDecl, position: name.positionAfterSkippingLeadingTrivia)
+    // Check if the current token is within a valid documentable symbol
+    if let symbol = token.ancestorOrSelf(mapping: { DocumentableSymbol(node: $0) }) {
+      return symbol
+    }
+    // Walk forward through the tokens until we find a documentable symbol
+    var previousToken: TokenSyntax? = token
+    while let nextToken = previousToken?.nextToken(viewMode: .sourceAccurate) {
+      if let symbol = nextToken.ancestorOrSelf(mapping: { DocumentableSymbol(node: $0) }) {
+        return symbol
       }
-      return nil
+      previousToken = nextToken
+    }
+    // Walk backwards through the tokens until we find a documentable symbol
+    previousToken = token
+    while let nextToken = previousToken?.previousToken(viewMode: .sourceAccurate) {
+      if let symbol = nextToken.ancestorOrSelf(mapping: { DocumentableSymbol(node: $0) }) {
+        return symbol
+      }
+      previousToken = nextToken
     }
+    // We couldn't find anything
+    return nil
   }
 }
 #endif
diff --git a/Tests/SourceKitLSPTests/DoccDocumentationTests.swift b/Tests/SourceKitLSPTests/DoccDocumentationTests.swift
index 40320f753..11f45ebe0 100644
--- a/Tests/SourceKitLSPTests/DoccDocumentationTests.swift
+++ b/Tests/SourceKitLSPTests/DoccDocumentationTests.swift
@@ -21,20 +21,39 @@ import SwiftDocC
 import XCTest
 
 final class DoccDocumentationTests: XCTestCase {
+
+  func testUnsupportedLanguage() async throws {
+    try await renderDocumentation(
+      markedText: "1️⃣",
+      language: .c,
+      expectedResponses: ["1️⃣": .error(.unsupportedLanguage(.c))]
+    )
+    try await renderDocumentation(
+      markedText: "2️⃣",
+      language: .cpp,
+      expectedResponses: ["2️⃣": .error(.unsupportedLanguage(.cpp))]
+    )
+    try await renderDocumentation(
+      markedText: "3️⃣",
+      language: .objective_c,
+      expectedResponses: ["3️⃣": .error(.unsupportedLanguage(.objective_c))]
+    )
+  }
+
   // MARK: Swift Documentation
 
   func testEmptySwiftFile() async throws {
     try await renderDocumentation(
-      swiftFile: "1️⃣",
+      markedText: "1️⃣",
       expectedResponses: [
-        "1️⃣": .error(.noDocumentation)
+        "1️⃣": .error(.noDocumentableSymbols)
       ]
     )
   }
 
   func testFunction() async throws {
     try await renderDocumentation(
-      swiftFile: """
+      markedText: """
         /// A function that do1️⃣es some important stuff.
         func func2️⃣tion() {
           // Some import3️⃣ant function contents.
@@ -44,14 +63,14 @@ final class DoccDocumentationTests: XCTestCase {
         "1️⃣": .renderNode(kind: .symbol, path: "test/function()"),
         "2️⃣": .renderNode(kind: .symbol, path: "test/function()"),
         "3️⃣": .renderNode(kind: .symbol, path: "test/function()"),
-        "4️⃣": .error(.noDocumentation),
+        "4️⃣": .renderNode(kind: .symbol, path: "test/function()"),
       ]
     )
   }
 
   func testStructure() async throws {
     try await renderDocumentation(
-      swiftFile: """
+      markedText: """
         /// A structure contain1️⃣ing important information.
         public struct Struc2️⃣ture {
           /// The inte3️⃣ger `foo`
@@ -76,14 +95,14 @@ final class DoccDocumentationTests: XCTestCase {
         "6️⃣": .renderNode(kind: .symbol, path: "test/Structure/bar"),
         "7️⃣": .renderNode(kind: .symbol, path: "test/Structure/init(_:bar:)"),
         "8️⃣": .renderNode(kind: .symbol, path: "test/Structure/init(_:bar:)"),
-        "9️⃣": .error(.noDocumentation),
+        "9️⃣": .renderNode(kind: .symbol, path: "test/Structure"),
       ]
     )
   }
 
   func testEmptyStructure() async throws {
     try await renderDocumentation(
-      swiftFile: """
+      markedText: """
         pub1️⃣lic struct Struc2️⃣ture {
           3️⃣
         }4️⃣
@@ -92,14 +111,33 @@ final class DoccDocumentationTests: XCTestCase {
         "1️⃣": .renderNode(kind: .symbol, path: "test/Structure"),
         "2️⃣": .renderNode(kind: .symbol, path: "test/Structure"),
         "3️⃣": .renderNode(kind: .symbol, path: "test/Structure"),
-        "4️⃣": .error(.noDocumentation),
+        "4️⃣": .renderNode(kind: .symbol, path: "test/Structure"),
+      ]
+    )
+  }
+
+  func testSubscriptDeclaration() async throws {
+    try await renderDocumentation(
+      markedText: """
+        /// A structure containing important information.
+        public struct Structure {
+          // Get the 1️⃣subscript at index
+          subscript(in2️⃣dex: Int) -> Int {
+            return i3️⃣ndex
+          }
+        }
+        """,
+      expectedResponses: [
+        "1️⃣": .renderNode(kind: .symbol, path: "test/Structure/subscript(_:)"),
+        "2️⃣": .renderNode(kind: .symbol, path: "test/Structure/subscript(_:)"),
+        "3️⃣": .renderNode(kind: .symbol, path: "test/Structure/subscript(_:)"),
       ]
     )
   }
 
   func testClass() async throws {
     try await renderDocumentation(
-      swiftFile: """
+      markedText: """
         /// A class contain1️⃣ing important information.
         public class Cla2️⃣ss {
           /// The inte3️⃣ger `foo`
@@ -125,14 +163,33 @@ final class DoccDocumentationTests: XCTestCase {
         "7️⃣": .renderNode(kind: .symbol, path: "test/Class/init(_:bar:)"),
         "8️⃣": .renderNode(kind: .symbol, path: "test/Class/init(_:bar:)"),
         "9️⃣": .renderNode(kind: .symbol, path: "test/Class"),
-        "0️⃣": .error(.noDocumentation),
+        "0️⃣": .renderNode(kind: .symbol, path: "test/Class"),
+      ]
+    )
+  }
+
+  func testClassDeInitializer() async throws {
+    try await renderDocumentation(
+      markedText: """
+        /// A class containing important information.
+        public class Class {
+          /// Initi1️⃣alize the class.
+          dein2️⃣it {
+            // De-initi3️⃣alize stuff
+          }
+        }
+        """,
+      expectedResponses: [
+        "1️⃣": .renderNode(kind: .symbol, path: "test/Class/deinit"),
+        "2️⃣": .renderNode(kind: .symbol, path: "test/Class/deinit"),
+        "3️⃣": .renderNode(kind: .symbol, path: "test/Class/deinit"),
       ]
     )
   }
 
   func testEmptyClass() async throws {
     try await renderDocumentation(
-      swiftFile: """
+      markedText: """
         pub1️⃣lic class Cla2️⃣ss {
           3️⃣
         }4️⃣
@@ -141,14 +198,14 @@ final class DoccDocumentationTests: XCTestCase {
         "1️⃣": .renderNode(kind: .symbol, path: "test/Class"),
         "2️⃣": .renderNode(kind: .symbol, path: "test/Class"),
         "3️⃣": .renderNode(kind: .symbol, path: "test/Class"),
-        "4️⃣": .error(.noDocumentation),
+        "4️⃣": .renderNode(kind: .symbol, path: "test/Class"),
       ]
     )
   }
 
   func testActor() async throws {
     try await renderDocumentation(
-      swiftFile: """
+      markedText: """
         /// An actor contain1️⃣ing important information.
         public actor Ac2️⃣tor {
           /// The inte3️⃣ger `foo`
@@ -173,14 +230,14 @@ final class DoccDocumentationTests: XCTestCase {
         "6️⃣": .renderNode(kind: .symbol, path: "test/Actor/bar"),
         "7️⃣": .renderNode(kind: .symbol, path: "test/Actor/init(_:bar:)"),
         "8️⃣": .renderNode(kind: .symbol, path: "test/Actor/init(_:bar:)"),
-        "9️⃣": .error(.noDocumentation),
+        "9️⃣": .renderNode(kind: .symbol, path: "test/Actor"),
       ]
     )
   }
 
   func testEmptyActor() async throws {
     try await renderDocumentation(
-      swiftFile: """
+      markedText: """
         pub1️⃣lic class Act2️⃣or {
           3️⃣
         }4️⃣
@@ -189,14 +246,14 @@ final class DoccDocumentationTests: XCTestCase {
         "1️⃣": .renderNode(kind: .symbol, path: "test/Actor"),
         "2️⃣": .renderNode(kind: .symbol, path: "test/Actor"),
         "3️⃣": .renderNode(kind: .symbol, path: "test/Actor"),
-        "4️⃣": .error(.noDocumentation),
+        "4️⃣": .renderNode(kind: .symbol, path: "test/Actor"),
       ]
     )
   }
 
   func testEnumeration() async throws {
     try await renderDocumentation(
-      swiftFile: """
+      markedText: """
         /// An enumeration contain1️⃣ing important information.
         public enum En2️⃣um {
           /// The 3️⃣first case.
@@ -218,7 +275,7 @@ final class DoccDocumentationTests: XCTestCase {
         "6️⃣": .renderNode(kind: .symbol, path: "test/Enum/second"),
         "7️⃣": .renderNode(kind: .symbol, path: "test/Enum/third(_:)"),
         "8️⃣": .renderNode(kind: .symbol, path: "test/Enum/third(_:)"),
-        "9️⃣": .error(.noDocumentation),
+        "9️⃣": .renderNode(kind: .symbol, path: "test/Enum"),
       ]
     )
   }
@@ -272,7 +329,7 @@ final class DoccDocumentationTests: XCTestCase {
 
   func testProtocol() async throws {
     try await renderDocumentation(
-      swiftFile: """
+      markedText: """
         /// A protocol contain1️⃣ing important information.
         public protocol Proto2️⃣col {
           /// The inte3️⃣ger `foo`
@@ -289,14 +346,14 @@ final class DoccDocumentationTests: XCTestCase {
         "4️⃣": .renderNode(kind: .symbol, path: "test/Protocol/foo"),
         "5️⃣": .renderNode(kind: .symbol, path: "test/Protocol/bar"),
         "6️⃣": .renderNode(kind: .symbol, path: "test/Protocol/bar"),
-        "7️⃣": .error(.noDocumentation),
+        "7️⃣": .renderNode(kind: .symbol, path: "test/Protocol"),
       ]
     )
   }
 
   func testEmptyProtocol() async throws {
     try await renderDocumentation(
-      swiftFile: """
+      markedText: """
         /// A protocol containing important information
         pub1️⃣lic struct Prot2️⃣ocol {
           3️⃣
@@ -306,19 +363,21 @@ final class DoccDocumentationTests: XCTestCase {
         "1️⃣": .renderNode(kind: .symbol, path: "test/Protocol"),
         "2️⃣": .renderNode(kind: .symbol, path: "test/Protocol"),
         "3️⃣": .renderNode(kind: .symbol, path: "test/Protocol"),
-        "4️⃣": .error(.noDocumentation),
+        "4️⃣": .renderNode(kind: .symbol, path: "test/Protocol"),
       ]
     )
   }
 
   func testExtension() async throws {
-    try await renderDocumentation(
-      swiftFile: """
+    let project = try await SwiftPMTestProject(
+      files: [
+        "MyLibrary/Structure.swift": """
         /// A structure containing important information
         public struct Structure {
           let number: Int
         }
-
+        """,
+        "MyLibrary/Extension.swift": """
         extension Stru1️⃣cture {
           /// One more than the number
           var numberPlusOne: Int {2️⃣ number + 1 }
@@ -329,16 +388,39 @@ final class DoccDocumentationTests: XCTestCase {
             case first
             /// The se5️⃣cond kind
             case second
-          }
-        }6️⃣
+          }6️⃣
+        }7️⃣
+        """,
+      ],
+      enableBackgroundIndexing: true
+    )
+    try await renderDocumentation(
+      fileName: "Extension.swift",
+      project: project,
+      expectedResponses: [
+        "1️⃣": .renderNode(kind: .symbol, path: "MyLibrary/Structure/numberPlusOne"),
+        "2️⃣": .renderNode(kind: .symbol, path: "MyLibrary/Structure/numberPlusOne"),
+        "3️⃣": .renderNode(kind: .symbol, path: "MyLibrary/Structure/Kind"),
+        "4️⃣": .renderNode(kind: .symbol, path: "MyLibrary/Structure/Kind/first"),
+        "5️⃣": .renderNode(kind: .symbol, path: "MyLibrary/Structure/Kind/second"),
+        "6️⃣": .renderNode(kind: .symbol, path: "MyLibrary/Structure/Kind"),
+        "7️⃣": .renderNode(kind: .symbol, path: "MyLibrary/Structure/Kind"),
+      ]
+    )
+  }
+
+  func testCursorInImport() async throws {
+    try await renderDocumentation(
+      markedText: """
+        import Found1️⃣ation
+
+        /// A structure containing important information
+        public struct Structure {
+          let number: Int
+        }
         """,
       expectedResponses: [
-        "1️⃣": .error(.noDocumentation),
-        "2️⃣": .renderNode(kind: .symbol, path: "test/Structure/numberPlusOne"),
-        "3️⃣": .renderNode(kind: .symbol, path: "test/Structure/Kind"),
-        "4️⃣": .renderNode(kind: .symbol, path: "test/Structure/Kind/first"),
-        "5️⃣": .renderNode(kind: .symbol, path: "test/Structure/Kind/second"),
-        "6️⃣": .error(.noDocumentation),
+        "1️⃣": .renderNode(kind: .symbol, path: "test/Structure")
       ]
     )
   }
@@ -709,13 +791,14 @@ fileprivate func renderDocumentation(
 }
 
 fileprivate func renderDocumentation(
-  swiftFile markedText: String,
+  markedText: String,
+  language: Language = .swift,
   expectedResponses: [String: PartialConvertResponse],
   file: StaticString = #filePath,
   line: UInt = #line
 ) async throws {
   let testClient = try await TestSourceKitLSPClient()
-  let uri = DocumentURI(for: .swift)
+  let uri = DocumentURI(for: language)
   let positions = testClient.openDocument(markedText, uri: uri)
 
   await renderDocumentation(