diff --git a/app/src/main/java/org/thoughtcrime/securesms/database/AttachmentTable.kt b/app/src/main/java/org/thoughtcrime/securesms/database/AttachmentTable.kt
index 87d6d79aa0..1e6342e462 100644
--- a/app/src/main/java/org/thoughtcrime/securesms/database/AttachmentTable.kt
+++ b/app/src/main/java/org/thoughtcrime/securesms/database/AttachmentTable.kt
@@ -307,8 +307,13 @@ class AttachmentTable(
 
     private const val QUOTE_THUMBNAIL_DIMEN = 200
     private const val QUOTE_THUMBAIL_QUALITY = 50
+
+    /** Indicates a legacy quote is pending transcoding to a new quote thumbnail. */
     const val QUOTE_PENDING_TRANSCODE = 2
 
+    /** Indicates a quote from a free-tier backup restore is pending potential reconstruction from a parent attachment. */
+    const val QUOTE_PENDING_RECONSTRUCTION = 3
+
     @JvmStatic
     @Throws(IOException::class)
     fun newDataFile(context: Context): File {
@@ -3163,6 +3168,96 @@ class AttachmentTable(
     )
   }
 
+  /**
+   * After restoring from the free-tier, it's possible we'll be missing many of our quoted replies.
+   * This marks quotes with a special flag to indicate that they'd be eligible for reconstruction.
+   * See [QUOTE_PENDING_RECONSTRUCTION].
+   */
+  fun markQuotesThatNeedReconstruction() {
+    writableDatabase
+      .update(TABLE_NAME)
+      .values(QUOTE to QUOTE_PENDING_RECONSTRUCTION)
+      .where("$QUOTE != 0 AND $DATA_FILE IS NULL AND $REMOTE_LOCATION IS NULL")
+      .run()
+  }
+
+  /**
+   * Retrieves data for the newest quote that is pending reconstruction (see [QUOTE_PENDING_RECONSTRUCTION]), if any.
+   */
+  fun getNewestQuotePendingReconstruction(): DatabaseAttachment? {
+    return readableDatabase
+      .select(*PROJECTION)
+      .from(TABLE_NAME)
+      .where("$QUOTE = $QUOTE_PENDING_RECONSTRUCTION")
+      .orderBy("$ID DESC")
+      .limit(1)
+      .run()
+      .readToSingleObject { it.readAttachment() }
+  }
+
+  /**
+   * After reconstructing a thumbnail, this method can be used to write the data to the quote.
+   * It'll handle duplicates as well as clearing the [QUOTE_PENDING_RECONSTRUCTION] flag.
+   */
+  @Throws(MmsException::class)
+  fun applyReconstructedQuoteData(attachmentId: AttachmentId, thumbnail: ImageCompressionUtil.Result) {
+    val newDataFileInfo = writeToDataFile(newDataFile(context), thumbnail.data.inputStream(), TransformProperties.empty())
+
+    val foundDuplicate = writableDatabase.withinTransaction { db ->
+      val existingMatch: DataFileInfo? = db
+        .select(*DATA_FILE_INFO_PROJECTION)
+        .from(TABLE_NAME)
+        .where("$DATA_HASH_END = ?", newDataFileInfo.hash)
+        .run()
+        .readToSingleObject { it.readDataFileInfo() }
+
+      db.update(TABLE_NAME)
+        .values(
+          DATA_FILE to (existingMatch?.file?.absolutePath ?: newDataFileInfo.file.absolutePath),
+          DATA_SIZE to (existingMatch?.length ?: newDataFileInfo.length),
+          DATA_RANDOM to (existingMatch?.random ?: newDataFileInfo.random),
+          DATA_HASH_START to (existingMatch?.hashStart ?: newDataFileInfo.hash),
+          DATA_HASH_END to (existingMatch?.hashEnd ?: newDataFileInfo.hash),
+          CONTENT_TYPE to thumbnail.mimeType,
+          WIDTH to thumbnail.width,
+          HEIGHT to thumbnail.height,
+          QUOTE to 1
+        )
+        .where("$ID = ?", attachmentId)
+        .run()
+
+      existingMatch != null
+    }
+
+    if (foundDuplicate) {
+      if (!newDataFileInfo.file.delete()) {
+        Log.w(TAG, "[applyReconstructedQuoteData] Failed to delete a duplicated file!")
+      }
+    }
+  }
+
+  /**
+   * Clears the [QUOTE_PENDING_RECONSTRUCTION] status of an attachment. Used for when an error occurs and you can't call [applyReconstructedQuoteData].
+   */
+  fun clearQuotePendingReconstruction(attachmentId: AttachmentId) {
+    writableDatabase
+      .update(TABLE_NAME)
+      .values(QUOTE to 1)
+      .where("$ID = ?", attachmentId)
+      .run()
+  }
+
+  /**
+   * Clears all [QUOTE_PENDING_RECONSTRUCTION] flags on attachments.
+   */
+  fun clearAllQuotesPendingReconstruction() {
+    writableDatabase
+      .update(TABLE_NAME)
+      .values(QUOTE to 1)
+      .where("$QUOTE = $QUOTE_PENDING_RECONSTRUCTION")
+      .run()
+  }
+
   /**
    * Used in an app migration that creates quote thumbnails. Updates all quote attachments that share the same
    * [previousDataFile] to use the new thumbnail.
diff --git a/app/src/main/java/org/thoughtcrime/securesms/database/MediaTable.kt b/app/src/main/java/org/thoughtcrime/securesms/database/MediaTable.kt
index 448852b524..54fedf23f3 100644
--- a/app/src/main/java/org/thoughtcrime/securesms/database/MediaTable.kt
+++ b/app/src/main/java/org/thoughtcrime/securesms/database/MediaTable.kt
@@ -39,6 +39,7 @@ class MediaTable internal constructor(context: Context?, databaseHelper: SignalD
         ${AttachmentTable.TABLE_NAME}.${AttachmentTable.WIDTH}, 
         ${AttachmentTable.TABLE_NAME}.${AttachmentTable.HEIGHT}, 
         ${AttachmentTable.TABLE_NAME}.${AttachmentTable.QUOTE}, 
+        ${AttachmentTable.TABLE_NAME}.${AttachmentTable.QUOTE_TARGET_CONTENT_TYPE},
         ${AttachmentTable.TABLE_NAME}.${AttachmentTable.STICKER_PACK_ID}, 
         ${AttachmentTable.TABLE_NAME}.${AttachmentTable.STICKER_PACK_KEY}, 
         ${AttachmentTable.TABLE_NAME}.${AttachmentTable.STICKER_ID}, 
diff --git a/app/src/main/java/org/thoughtcrime/securesms/jobs/CheckRestoreMediaLeftJob.kt b/app/src/main/java/org/thoughtcrime/securesms/jobs/CheckRestoreMediaLeftJob.kt
index 6ec5ff4cea..6be74760a2 100644
--- a/app/src/main/java/org/thoughtcrime/securesms/jobs/CheckRestoreMediaLeftJob.kt
+++ b/app/src/main/java/org/thoughtcrime/securesms/jobs/CheckRestoreMediaLeftJob.kt
@@ -10,6 +10,7 @@ import org.thoughtcrime.securesms.backup.DeletionState
 import org.thoughtcrime.securesms.backup.RestoreState
 import org.thoughtcrime.securesms.backup.v2.ArchiveRestoreProgress
 import org.thoughtcrime.securesms.database.SignalDatabase
+import org.thoughtcrime.securesms.dependencies.AppDependencies
 import org.thoughtcrime.securesms.jobmanager.Job
 import org.thoughtcrime.securesms.keyvalue.SignalStore
 import org.thoughtcrime.securesms.service.BackupMediaRestoreService
@@ -55,6 +56,11 @@ class CheckRestoreMediaLeftJob private constructor(parameters: Parameters) : Job
         if (SignalStore.backup.deletionState == DeletionState.AWAITING_MEDIA_DOWNLOAD) {
           SignalStore.backup.deletionState = DeletionState.MEDIA_DOWNLOAD_FINISHED
         }
+
+        if (!SignalStore.backup.backsUpMedia) {
+          SignalDatabase.attachments.markQuotesThatNeedReconstruction()
+          AppDependencies.jobManager.add(QuoteThumbnailReconstructionJob())
+        }
       }
     } else if (runAttempt == 0) {
       Log.w(TAG, "Still have remaining data to restore, will retry before checking job queues, queue: ${parameters.queue} estimated remaining: $remainingAttachmentSize")
diff --git a/app/src/main/java/org/thoughtcrime/securesms/jobs/JobManagerFactories.java b/app/src/main/java/org/thoughtcrime/securesms/jobs/JobManagerFactories.java
index c74b1e597b..67dfa82b4f 100644
--- a/app/src/main/java/org/thoughtcrime/securesms/jobs/JobManagerFactories.java
+++ b/app/src/main/java/org/thoughtcrime/securesms/jobs/JobManagerFactories.java
@@ -235,6 +235,7 @@ public final class JobManagerFactories {
       put(PushProcessMessageErrorJob.KEY,              new PushProcessMessageErrorJob.Factory());
       put(PushProcessMessageJob.KEY,                   new PushProcessMessageJob.Factory());
       put(QuoteThumbnailBackfillJob.KEY,               new QuoteThumbnailBackfillJob.Factory());
+      put(QuoteThumbnailReconstructionJob.KEY,         new QuoteThumbnailReconstructionJob.Factory());
       put(ReactionSendJob.KEY,                         new ReactionSendJob.Factory());
       put(RebuildMessageSearchIndexJob.KEY,            new RebuildMessageSearchIndexJob.Factory());
       put(ReclaimUsernameAndLinkJob.KEY,               new ReclaimUsernameAndLinkJob.Factory());
diff --git a/app/src/main/java/org/thoughtcrime/securesms/jobs/QuoteThumbnailBackfillJob.kt b/app/src/main/java/org/thoughtcrime/securesms/jobs/QuoteThumbnailBackfillJob.kt
index 5671c39bce..440789037a 100644
--- a/app/src/main/java/org/thoughtcrime/securesms/jobs/QuoteThumbnailBackfillJob.kt
+++ b/app/src/main/java/org/thoughtcrime/securesms/jobs/QuoteThumbnailBackfillJob.kt
@@ -33,7 +33,7 @@ import org.thoughtcrime.securesms.mms.PartAuthority
 
 /**
  * This job processes quote attachments to generate thumbnails where possible.
- * In order to avoid hammering the device, this job will process a single attachment
+ * In order to avoid hammering the device, this job will process a few attachments
  * and then reschedule itself to run again if necessary.
  */
 class QuoteThumbnailBackfillJob private constructor(parameters: Parameters) : Job(parameters) {
diff --git a/app/src/main/java/org/thoughtcrime/securesms/jobs/QuoteThumbnailReconstructionJob.kt b/app/src/main/java/org/thoughtcrime/securesms/jobs/QuoteThumbnailReconstructionJob.kt
new file mode 100644
index 0000000000..47fd5ea75f
--- /dev/null
+++ b/app/src/main/java/org/thoughtcrime/securesms/jobs/QuoteThumbnailReconstructionJob.kt
@@ -0,0 +1,121 @@
+/*
+ * Copyright 2025 Signal Messenger, LLC
+ * SPDX-License-Identifier: AGPL-3.0-only
+ */
+
+package org.thoughtcrime.securesms.jobs
+
+import org.signal.core.util.logging.Log
+import org.thoughtcrime.securesms.attachments.DatabaseAttachment
+import org.thoughtcrime.securesms.database.AttachmentTable
+import org.thoughtcrime.securesms.database.SignalDatabase
+import org.thoughtcrime.securesms.dependencies.AppDependencies
+import org.thoughtcrime.securesms.jobmanager.Job
+import org.thoughtcrime.securesms.mms.DecryptableUri
+import org.thoughtcrime.securesms.util.MediaUtil
+import org.thoughtcrime.securesms.util.RemoteConfig
+import org.thoughtcrime.securesms.util.getQuote
+import kotlin.time.Duration.Companion.milliseconds
+
+/**
+ * A job that should be enqueued after a free-tier backup restore completes.
+ * Before enqueueing this job, be sure to call [AttachmentTable.markQuotesThatNeedReconstruction].
+ */
+class QuoteThumbnailReconstructionJob private constructor(params: Parameters) : Job(params) {
+
+  companion object {
+    private val TAG = Log.tag(QuoteThumbnailReconstructionJob::class)
+
+    const val KEY = "QuoteThumbnailReconstructionJob"
+  }
+
+  private var activeQuoteAttachment: DatabaseAttachment? = null
+
+  constructor() : this(
+    Parameters.Builder()
+      .setLifespan(Parameters.IMMORTAL)
+      .setMaxInstancesForFactory(2)
+      .build()
+  )
+
+  override fun serialize(): ByteArray? = null
+
+  override fun getFactoryKey() = KEY
+
+  override fun run(): Result {
+    val quoteAttachment = SignalDatabase.attachments.getNewestQuotePendingReconstruction()
+    if (quoteAttachment == null) {
+      Log.i(TAG, "No remaining quotes to reconstruct. Done!")
+      return Result.success()
+    }
+
+    activeQuoteAttachment = quoteAttachment
+
+    val message = SignalDatabase.messages.getMessageRecordOrNull(quoteAttachment.mmsId)
+    if (message == null) {
+      Log.w(TAG, "Failed to find message for quote attachment. Possible race condition where it was just deleted. Marking as migrated and continuing.")
+      SignalDatabase.attachments.clearQuotePendingReconstruction(quoteAttachment.attachmentId)
+      AppDependencies.jobManager.add(QuoteThumbnailReconstructionJob())
+      return Result.success()
+    }
+
+    if (message.getQuote() == null) {
+      Log.w(TAG, "The target message has no quote data. Marking as migrated and continuing.")
+      SignalDatabase.attachments.clearQuotePendingReconstruction(quoteAttachment.attachmentId)
+      AppDependencies.jobManager.add(QuoteThumbnailReconstructionJob())
+      return Result.success()
+    }
+
+    val messageAge = System.currentTimeMillis().milliseconds - message.dateReceived.milliseconds
+    if (messageAge > RemoteConfig.messageQueueTime.milliseconds) {
+      Log.w(TAG, "Target message is older than the message queue time. Clearing remaining pending quotes and ending the reconstruction process.")
+      SignalDatabase.attachments.clearAllQuotesPendingReconstruction()
+      return Result.success()
+    }
+
+    val targetMessage = SignalDatabase.messages.getMessageFor(message.getQuote()!!.id, message.getQuote()!!.author)
+    if (targetMessage == null) {
+      Log.w(TAG, "Failed to find the target message of the quote. Marking as migrated and continuing.")
+      SignalDatabase.attachments.clearQuotePendingReconstruction(quoteAttachment.attachmentId)
+      AppDependencies.jobManager.add(QuoteThumbnailReconstructionJob())
+      return Result.success()
+    }
+
+    val targetAttachment = SignalDatabase.attachments.getAttachmentsForMessage(targetMessage.id).firstOrNull { MediaUtil.isImageOrVideoType(it.contentType) && it.uri != null }
+    if (targetAttachment == null) {
+      Log.w(TAG, "No applicable attachments found for the target message. Marking as migrated and continuing.")
+      SignalDatabase.attachments.clearQuotePendingReconstruction(quoteAttachment.attachmentId)
+      AppDependencies.jobManager.add(QuoteThumbnailReconstructionJob())
+      return Result.success()
+    }
+
+    val thumbnailData = SignalDatabase.attachments.generateQuoteThumbnail(DecryptableUri(targetAttachment.uri!!), targetAttachment.contentType, quiet = true)
+    if (thumbnailData == null) {
+      Log.w(TAG, "Failed to generate a thumbnail for the attachment. Marking as migrated and continuing.")
+      SignalDatabase.attachments.clearQuotePendingReconstruction(quoteAttachment.attachmentId)
+      AppDependencies.jobManager.add(QuoteThumbnailReconstructionJob())
+      return Result.success()
+    }
+
+    SignalDatabase.attachments.applyReconstructedQuoteData(quoteAttachment.attachmentId, thumbnailData)
+    Log.d(TAG, "Successfully reconstructed quote attachment for ${quoteAttachment.attachmentId}")
+
+    AppDependencies.jobManager.add(QuoteThumbnailReconstructionJob())
+    return Result.success()
+  }
+
+  override fun onFailure() {
+    activeQuoteAttachment?.let { attachment ->
+      Log.w(TAG, "Failed during reconstruction. Marking as migrated and continuing.", true)
+      SignalDatabase.attachments.clearQuotePendingReconstruction(attachment.attachmentId)
+    } ?: Log.w(TAG, "Job failed, but no active file is set!")
+
+    AppDependencies.jobManager.add(QuoteThumbnailReconstructionJob())
+  }
+
+  class Factory : Job.Factory<QuoteThumbnailReconstructionJob> {
+    override fun create(params: Parameters, data: ByteArray?): QuoteThumbnailReconstructionJob {
+      return QuoteThumbnailReconstructionJob(params)
+    }
+  }
+}