diff --git a/src/main/kotlin/link/infra/packwiz/installer/DownloadTask.kt b/src/main/kotlin/link/infra/packwiz/installer/DownloadTask.kt
index e5de0d2..917550a 100644
--- a/src/main/kotlin/link/infra/packwiz/installer/DownloadTask.kt
+++ b/src/main/kotlin/link/infra/packwiz/installer/DownloadTask.kt
@@ -21,6 +21,7 @@ import java.nio.file.StandardCopyOption
 
 internal class DownloadTask private constructor(val metadata: IndexFile.File, val index: IndexFile, private val downloadSide: Side) : IOptionDetails {
 	var cachedFile: ManifestFile.File? = null
+		private set
 
 	private var err: Exception? = null
 	val exceptionDetails get() = err?.let { e -> ExceptionDetails(name, e) }
@@ -28,10 +29,24 @@ internal class DownloadTask private constructor(val metadata: IndexFile.File, va
 	fun failed() = err != null
 
 	var alreadyUpToDate = false
+		private set
 	private var metadataRequired = true
 	private var invalidated = false
 	// If file is new or isOptional changed to true, the option needs to be presented again
 	private var newOptional = true
+	var completionStatus = CompletionStatus.INCOMPLETE
+		private set
+
+	enum class CompletionStatus {
+		INCOMPLETE,
+		DOWNLOADED,
+		ALREADY_EXISTS_CACHED,
+		ALREADY_EXISTS_VALIDATED,
+		SKIPPED_DISABLED,
+		SKIPPED_WRONG_SIDE,
+		DELETED_DISABLED,
+		DELETED_WRONG_SIDE;
+	}
 
 	val isOptional get() = metadata.linkedFile?.option?.optional ?: false
 
@@ -76,6 +91,7 @@ internal class DownloadTask private constructor(val metadata: IndexFile.File, va
 			if (currHash == cachedFile.hash) { // Already up to date
 				alreadyUpToDate = true
 				metadataRequired = false
+				completionStatus = CompletionStatus.ALREADY_EXISTS_CACHED
 			}
 		}
 		if (cachedFile.isOptional) {
@@ -143,6 +159,7 @@ internal class DownloadTask private constructor(val metadata: IndexFile.File, va
 					fileSource.buffer().readAll(blackholeSink())
 					if (hash == fileSource.hash) {
 						alreadyUpToDate = true
+						completionStatus = CompletionStatus.ALREADY_EXISTS_VALIDATED
 
 						// Update the manifest file
 						cachedFile = (cachedFile ?: ManifestFile.File()).also {
@@ -181,10 +198,18 @@ internal class DownloadTask private constructor(val metadata: IndexFile.File, va
 				if (it.cachedLocation != null) {
 					// Ensure wrong-side or optional false files are removed
 					try {
-						Files.deleteIfExists(it.cachedLocation!!.nioPath)
+						completionStatus = if (Files.deleteIfExists(it.cachedLocation!!.nioPath)) {
+							if (correctSide()) { CompletionStatus.DELETED_DISABLED } else { CompletionStatus.DELETED_WRONG_SIDE }
+						} else {
+							if (correctSide()) { CompletionStatus.SKIPPED_DISABLED } else { CompletionStatus.SKIPPED_WRONG_SIDE }
+						}
 					} catch (e: IOException) {
 						Log.warn("Failed to delete file", e)
 					}
+				} else {
+					completionStatus =
+						if (correctSide()) { CompletionStatus.SKIPPED_DISABLED }
+						else { CompletionStatus.SKIPPED_WRONG_SIDE }
 				}
 				it.cachedLocation = null
 				return
@@ -284,6 +309,8 @@ internal class DownloadTask private constructor(val metadata: IndexFile.File, va
 				}
 			}
 		}
+
+		completionStatus = CompletionStatus.DOWNLOADED
 	}
 
 	companion object {
diff --git a/src/main/kotlin/link/infra/packwiz/installer/UpdateManager.kt b/src/main/kotlin/link/infra/packwiz/installer/UpdateManager.kt
index 389b898..1f1c2dc 100644
--- a/src/main/kotlin/link/infra/packwiz/installer/UpdateManager.kt
+++ b/src/main/kotlin/link/infra/packwiz/installer/UpdateManager.kt
@@ -247,31 +247,17 @@ class UpdateManager internal constructor(private val opts: Options, val ui: IUse
 		}
 
 		ui.submitProgress(InstallProgress("Checking local files..."))
-		// TODO: use kotlin filtering/FP rather than an iterator?
 		val it: MutableIterator<Map.Entry<PackwizFilePath, ManifestFile.File>> = manifest.cachedFiles.entries.iterator()
 		while (it.hasNext()) {
 			val (uri, file) = it.next()
 			if (file.cachedLocation != null) {
-				var alreadyDeleted = false
-				// Delete if option value has been set to false
-				if (file.isOptional && !file.optionValue) {
+				if (indexFile.files.none { it.file.rebase(opts.packFolder) == uri }) { // File has been removed from the index
 					try {
 						Files.deleteIfExists(file.cachedLocation!!.nioPath)
 					} catch (e: IOException) {
-						Log.warn("Failed to delete optional disabled file", e)
-					}
-					// Set to null, as it doesn't exist anymore
-					file.cachedLocation = null
-					alreadyDeleted = true
-				}
-				if (indexFile.files.none { it.file.rebase(opts.packFolder) == uri }) { // File has been removed from the index
-					if (!alreadyDeleted) {
-						try {
-							Files.deleteIfExists(file.cachedLocation!!.nioPath)
-						} catch (e: IOException) {
-							Log.warn("Failed to delete file removed from index", e)
-						}
+						Log.warn("Failed to delete file removed from index", e)
 					}
+					Log.info("Deleted ${file.cachedLocation!!.filename} (removed from pack)")
 					it.remove()
 				}
 			}
@@ -401,7 +387,16 @@ class UpdateManager internal constructor(private val opts: Options, val ui: IUse
 			val progress = if (exDetails != null) {
 				"Failed to download ${exDetails.name}: ${exDetails.exception.message}"
 			} else {
-				"Downloaded ${task.name}"
+				when (task.completionStatus) {
+					DownloadTask.CompletionStatus.INCOMPLETE -> "${task.name} pending (you should never see this...)"
+					DownloadTask.CompletionStatus.DOWNLOADED -> "Downloaded ${task.name}"
+					DownloadTask.CompletionStatus.ALREADY_EXISTS_CACHED -> "${task.name} already exists (cached)"
+					DownloadTask.CompletionStatus.ALREADY_EXISTS_VALIDATED -> "${task.name} already exists (validated)"
+					DownloadTask.CompletionStatus.SKIPPED_DISABLED -> "Skipped ${task.name} (disabled)"
+					DownloadTask.CompletionStatus.SKIPPED_WRONG_SIDE -> "Skipped ${task.name} (wrong side)"
+					DownloadTask.CompletionStatus.DELETED_DISABLED -> "Deleted ${task.name} (disabled)"
+					DownloadTask.CompletionStatus.DELETED_WRONG_SIDE -> "Deleted ${task.name} (wrong side)"
+				}
 			}
 			ui.submitProgress(InstallProgress(progress, i + 1, tasks.size))