diff --git a/app/src/main/java/app/pachli/components/compose/ComposeActivity.kt b/app/src/main/java/app/pachli/components/compose/ComposeActivity.kt
index 45904447b..ec6bf31af 100644
--- a/app/src/main/java/app/pachli/components/compose/ComposeActivity.kt
+++ b/app/src/main/java/app/pachli/components/compose/ComposeActivity.kt
@@ -109,7 +109,9 @@ import app.pachli.util.setDrawableTint
 import com.canhub.cropper.CropImage
 import com.canhub.cropper.CropImageContract
 import com.canhub.cropper.options
+import com.github.michaelbull.result.Result
 import com.github.michaelbull.result.getOrElse
+import com.github.michaelbull.result.mapBoth
 import com.github.michaelbull.result.onFailure
 import com.google.android.material.bottomsheet.BottomSheetBehavior
 import com.google.android.material.color.MaterialColors
@@ -253,7 +255,7 @@ class ComposeActivity :
         val mediaAdapter = MediaPreviewAdapter(
             this,
             onAddCaption = { item ->
-                CaptionDialog.newInstance(item.localId, item.description, item.uri).show(supportFragmentManager, "caption_dialog")
+                CaptionDialog.newInstance(item.localId, item.serverId, item.description, item.uri).show(supportFragmentManager, "caption_dialog")
             },
             onAddFocus = { item ->
                 makeFocusDialog(item.focus, item.uri) { newFocus ->
@@ -524,14 +526,6 @@ class ComposeActivity :
                 enablePollButton(media.isEmpty())
             }.collect()
         }
-
-        lifecycleScope.launch {
-            viewModel.uploadError.collect { mediaUploaderError ->
-                val message = mediaUploaderError.fmt(this@ComposeActivity)
-
-                displayPermamentMessage(getString(R.string.error_media_upload_sending_fmt, message))
-            }
-        }
     }
 
     /** @return List of states of the different bottomsheets */
@@ -1272,14 +1266,8 @@ class ComposeActivity :
      * User is editing a new post, and can either save the changes as a draft or discard them.
      */
     private fun getSaveAsDraftOrDiscardDialog(contentText: String, contentWarning: String): AlertDialog.Builder {
-        val warning = if (viewModel.media.value.isNotEmpty()) {
-            R.string.compose_save_draft_loses_media
-        } else {
-            R.string.compose_save_draft
-        }
-
-        return AlertDialog.Builder(this)
-            .setMessage(warning)
+        val builder = AlertDialog.Builder(this)
+            .setTitle(R.string.compose_save_draft)
             .setPositiveButton(R.string.action_save) { _, _ ->
                 viewModel.stopUploads()
                 saveDraftAndFinish(contentText, contentWarning)
@@ -1288,6 +1276,12 @@ class ComposeActivity :
                 viewModel.stopUploads()
                 deleteDraftAndFinish()
             }
+
+        if (viewModel.media.value.isNotEmpty()) {
+            builder.setMessage(R.string.compose_save_draft_loses_media)
+        }
+
+        return builder
     }
 
     /**
@@ -1295,14 +1289,8 @@ class ComposeActivity :
      * discard them.
      */
     private fun getUpdateDraftOrDiscardDialog(contentText: String, contentWarning: String): AlertDialog.Builder {
-        val warning = if (viewModel.media.value.isNotEmpty()) {
-            R.string.compose_save_draft_loses_media
-        } else {
-            R.string.compose_save_draft
-        }
-
-        return AlertDialog.Builder(this)
-            .setMessage(warning)
+        val builder = AlertDialog.Builder(this)
+            .setTitle(R.string.compose_save_draft)
             .setPositiveButton(R.string.action_save) { _, _ ->
                 viewModel.stopUploads()
                 saveDraftAndFinish(contentText, contentWarning)
@@ -1311,6 +1299,12 @@ class ComposeActivity :
                 viewModel.stopUploads()
                 finish()
             }
+
+        if (viewModel.media.value.isNotEmpty()) {
+            builder.setMessage(R.string.compose_save_draft_loses_media)
+        }
+
+        return builder
     }
 
     /**
@@ -1392,23 +1386,39 @@ class ComposeActivity :
         val uri: Uri,
         val type: Type,
         val mediaSize: Long,
-        val uploadPercent: Int = 0,
-        val id: String? = null,
         val description: String? = null,
         val focus: Attachment.Focus? = null,
-        val state: State,
+        val uploadState: Result<UploadState, MediaUploaderError>,
     ) {
         enum class Type {
             IMAGE,
             VIDEO,
             AUDIO,
         }
-        enum class State {
-            UPLOADING,
-            UNPROCESSED,
-            PROCESSED,
-            PUBLISHED,
-        }
+
+        /**
+         * Server's ID for this attachment. May be null if the media is still
+         * being uploaded, or it was uploaded and there was an error that
+         * meant it couldn't be processed. Attachments that have an error
+         * *after* processing have a non-null `serverId`.
+         */
+        val serverId: String?
+            get() = uploadState.mapBoth(
+                { state ->
+                    when (state) {
+                        is UploadState.Uploading -> null
+                        is UploadState.Uploaded.Processing -> state.serverId
+                        is UploadState.Uploaded.Processed -> state.serverId
+                        is UploadState.Uploaded.Published -> state.serverId
+                    }
+                },
+                { error ->
+                    when (error) {
+                        is MediaUploaderError.UpdateMediaError -> error.serverId
+                        else -> null
+                    }
+                },
+            )
     }
 
     override fun onTimeSet(time: Date?) {
@@ -1425,8 +1435,8 @@ class ComposeActivity :
         scheduleBehavior.state = BottomSheetBehavior.STATE_HIDDEN
     }
 
-    override fun onUpdateDescription(localId: Int, description: String) {
-        viewModel.updateDescription(localId, description)
+    override fun onUpdateDescription(localId: Int, serverId: String?, description: String) {
+        viewModel.updateDescription(localId, serverId, description)
     }
 
     companion object {
diff --git a/app/src/main/java/app/pachli/components/compose/ComposeViewModel.kt b/app/src/main/java/app/pachli/components/compose/ComposeViewModel.kt
index 94534f5f6..87a862eaf 100644
--- a/app/src/main/java/app/pachli/components/compose/ComposeViewModel.kt
+++ b/app/src/main/java/app/pachli/components/compose/ComposeViewModel.kt
@@ -28,6 +28,7 @@ import androidx.lifecycle.viewModelScope
 import app.pachli.R
 import app.pachli.components.compose.ComposeActivity.QueuedMedia
 import app.pachli.components.compose.ComposeAutoCompleteAdapter.AutocompleteResult
+import app.pachli.components.compose.UploadState.Uploaded
 import app.pachli.components.drafts.DraftHelper
 import app.pachli.components.search.SearchType
 import app.pachli.core.common.PachliError
@@ -52,20 +53,20 @@ import at.connyduck.calladapter.networkresult.fold
 import com.github.michaelbull.result.Err
 import com.github.michaelbull.result.Ok
 import com.github.michaelbull.result.Result
+import com.github.michaelbull.result.andThen
 import com.github.michaelbull.result.get
 import com.github.michaelbull.result.getOrElse
 import com.github.michaelbull.result.mapBoth
 import com.github.michaelbull.result.mapError
+import com.github.michaelbull.result.onFailure
+import com.github.michaelbull.result.onSuccess
 import dagger.hilt.android.lifecycle.HiltViewModel
 import io.github.z4kn4fein.semver.constraints.toConstraint
 import java.util.Date
 import javax.inject.Inject
 import kotlinx.coroutines.Dispatchers
-import kotlinx.coroutines.channels.BufferOverflow
-import kotlinx.coroutines.flow.MutableSharedFlow
 import kotlinx.coroutines.flow.MutableStateFlow
 import kotlinx.coroutines.flow.SharingStarted
-import kotlinx.coroutines.flow.asSharedFlow
 import kotlinx.coroutines.flow.asStateFlow
 import kotlinx.coroutines.flow.map
 import kotlinx.coroutines.flow.stateIn
@@ -144,8 +145,6 @@ class ComposeViewModel @Inject constructor(
 
     private val _media: MutableStateFlow<List<QueuedMedia>> = MutableStateFlow(emptyList())
     val media = _media.asStateFlow()
-    private val _uploadError = MutableSharedFlow<MediaUploaderError>(replay = 0, extraBufferCapacity = 1, onBufferOverflow = BufferOverflow.DROP_OLDEST)
-    val uploadError = _uploadError.asSharedFlow()
     private val _closeConfirmation = MutableStateFlow(ConfirmationKind.NONE)
     val closeConfirmation = _closeConfirmation.asStateFlow()
     private val _statusLength = MutableStateFlow(0)
@@ -227,7 +226,7 @@ class ComposeViewModel @Inject constructor(
                 mediaSize = mediaSize,
                 description = description,
                 focus = focus,
-                state = QueuedMedia.State.UPLOADING,
+                uploadState = Ok(UploadState.Uploading(percentage = 0)),
             )
             stashMediaItem = mediaItem
 
@@ -245,35 +244,8 @@ class ComposeViewModel @Inject constructor(
         viewModelScope.launch {
             mediaUploader
                 .uploadMedia(mediaItem, instanceInfo.value)
-                .collect { event ->
-                    val item = media.value.find { it.localId == mediaItem.localId }
-                        ?: return@collect
-                    var newMediaItem: QueuedMedia? = null
-                    val uploadEvent = event.getOrElse {
-                        _media.update { mediaList -> mediaList.filter { it.localId != mediaItem.localId } }
-                        _uploadError.emit(it)
-                        return@collect
-                    }
-
-                    newMediaItem = when (uploadEvent) {
-                        is UploadEvent.ProgressEvent -> item.copy(uploadPercent = uploadEvent.percentage)
-                        is UploadEvent.FinishedEvent -> {
-                            item.copy(
-                                id = uploadEvent.media.mediaId,
-                                uploadPercent = -1,
-                                state = if (uploadEvent.media.processed) {
-                                    QueuedMedia.State.PROCESSED
-                                } else {
-                                    QueuedMedia.State.UNPROCESSED
-                                },
-                            )
-                        }
-                    }
-                    newMediaItem.let {
-                        _media.update { mediaList ->
-                            mediaList.map { mediaItem -> if (mediaItem.localId == it.localId) it else mediaItem }
-                        }
-                    }
+                .collect { uploadResult ->
+                    updateMediaItem(mediaItem.localId) { it.copy(uploadState = uploadResult) }
                 }
         }
 
@@ -288,11 +260,9 @@ class ComposeViewModel @Inject constructor(
                 uri = uri,
                 type = type,
                 mediaSize = 0,
-                uploadPercent = -1,
-                id = id,
                 description = description,
                 focus = focus,
-                state = QueuedMedia.State.PUBLISHED,
+                uploadState = Ok(Uploaded.Published(id)),
             )
             mediaList + mediaItem
         }
@@ -457,11 +427,11 @@ class ComposeViewModel @Inject constructor(
         val attachedMedia = media.value.map { item ->
             MediaToSend(
                 localId = item.localId,
-                id = item.id,
+                id = item.serverId,
                 uri = item.uri.toString(),
                 description = item.description,
                 focus = item.focus,
-                processed = item.state == QueuedMedia.State.PROCESSED || item.state == QueuedMedia.State.PUBLISHED,
+                processed = item.uploadState.get() is Uploaded.Processed || item.uploadState.get() is Uploaded.Published,
             )
         }
         val tootToSend = StatusToSend(
@@ -498,16 +468,45 @@ class ComposeViewModel @Inject constructor(
         }
     }
 
-    fun updateDescription(localId: Int, description: String) {
-        updateMediaItem(localId) { mediaItem ->
-            mediaItem.copy(description = description)
+    fun updateDescription(localId: Int, serverId: String?, description: String) {
+        // If the image hasn't been uploaded then update the state locally.
+        if (serverId == null) {
+            updateMediaItem(localId) { mediaItem -> mediaItem.copy(description = description) }
+            return
+        }
+
+        // Update the remote description and report any errors. Update the local description
+        // if there are errors so the user still has the text and can try and correct it.
+        viewModelScope.launch {
+            api.updateMedia(serverId, description = description)
+                .andThen { api.getMedia(serverId) }
+                .onSuccess { response ->
+                    val state = if (response.code == 200) {
+                        Uploaded.Processed(serverId)
+                    } else {
+                        Uploaded.Processing(serverId)
+                    }
+                    updateMediaItem(localId) {
+                        it.copy(
+                            description = description,
+                            uploadState = Ok(state),
+                        )
+                    }
+                }
+                .mapError { MediaUploaderError.UpdateMediaError(serverId, it) }
+                .onFailure { error ->
+                    updateMediaItem(localId) {
+                        it.copy(
+                            description = description,
+                            uploadState = Err(error),
+                        )
+                    }
+                }
         }
     }
 
     fun updateFocus(localId: Int, focus: Attachment.Focus) {
-        updateMediaItem(localId) { mediaItem ->
-            mediaItem.copy(focus = focus)
-        }
+        updateMediaItem(localId) { mediaItem -> mediaItem.copy(focus = focus) }
     }
 
     suspend fun searchAutocompleteSuggestions(token: String): List<AutocompleteResult> {
diff --git a/app/src/main/java/app/pachli/components/compose/MediaPreviewAdapter.kt b/app/src/main/java/app/pachli/components/compose/MediaPreviewAdapter.kt
index c37957017..1b7e4a601 100644
--- a/app/src/main/java/app/pachli/components/compose/MediaPreviewAdapter.kt
+++ b/app/src/main/java/app/pachli/components/compose/MediaPreviewAdapter.kt
@@ -21,30 +21,44 @@ import android.view.View
 import android.view.ViewGroup
 import android.widget.ImageView
 import android.widget.PopupMenu
+import androidx.appcompat.app.AlertDialog
 import androidx.constraintlayout.widget.ConstraintLayout
 import androidx.recyclerview.widget.AsyncListDiffer
 import androidx.recyclerview.widget.DiffUtil
 import androidx.recyclerview.widget.RecyclerView
 import app.pachli.R
+import app.pachli.components.compose.ComposeActivity.QueuedMedia
+import app.pachli.components.compose.UploadState.Uploaded
 import app.pachli.components.compose.view.ProgressImageView
 import app.pachli.core.designsystem.R as DR
 import com.bumptech.glide.Glide
 import com.bumptech.glide.load.engine.DiskCacheStrategy
+import com.github.michaelbull.result.get
+import com.github.michaelbull.result.onFailure
+import com.github.michaelbull.result.onSuccess
 
 class MediaPreviewAdapter(
     context: Context,
-    private val onAddCaption: (ComposeActivity.QueuedMedia) -> Unit,
-    private val onAddFocus: (ComposeActivity.QueuedMedia) -> Unit,
-    private val onEditImage: (ComposeActivity.QueuedMedia) -> Unit,
-    private val onRemove: (ComposeActivity.QueuedMedia) -> Unit,
+    private val onAddCaption: (QueuedMedia) -> Unit,
+    private val onAddFocus: (QueuedMedia) -> Unit,
+    private val onEditImage: (QueuedMedia) -> Unit,
+    private val onRemove: (QueuedMedia) -> Unit,
 ) : RecyclerView.Adapter<MediaPreviewAdapter.PreviewViewHolder>() {
 
-    fun submitList(list: List<ComposeActivity.QueuedMedia>) {
+    fun submitList(list: List<QueuedMedia>) {
         this.differ.submitList(list)
     }
 
     private fun onMediaClick(position: Int, view: View) {
         val item = differ.currentList[position]
+
+        // Handle error
+        item.uploadState
+            .onSuccess { showMediaPopup(item, view) }
+            .onFailure { showMediaError(item, it, view) }
+    }
+
+    private fun showMediaPopup(item: QueuedMedia, view: View) {
         val popup = PopupMenu(view.context, view)
         val addCaptionId = 1
         val addFocusId = 2
@@ -52,9 +66,9 @@ class MediaPreviewAdapter(
         val removeId = 4
 
         popup.menu.add(0, addCaptionId, 0, R.string.action_set_caption)
-        if (item.type == ComposeActivity.QueuedMedia.Type.IMAGE) {
+        if (item.type == QueuedMedia.Type.IMAGE) {
             popup.menu.add(0, addFocusId, 0, R.string.action_set_focus)
-            if (item.state != ComposeActivity.QueuedMedia.State.PUBLISHED) {
+            if (item.uploadState.get() !is Uploaded.Published) {
                 // Already-published items can't be edited
                 popup.menu.add(0, editImageId, 0, R.string.action_edit_image)
             }
@@ -72,6 +86,15 @@ class MediaPreviewAdapter(
         popup.show()
     }
 
+    private fun showMediaError(item: QueuedMedia, error: MediaUploaderError, view: View) {
+        AlertDialog.Builder(view.context)
+            .setTitle(R.string.action_post_failed)
+            .setMessage(view.context.getString(R.string.upload_failed_msg_fmt, error.fmt(view.context)))
+            .setPositiveButton(android.R.string.ok) { _, _ -> }
+            .setNegativeButton(R.string.upload_failed_modify_attachment) { _, _ -> showMediaPopup(item, view) }
+            .show()
+    }
+
     private val thumbnailViewSize =
         context.resources.getDimensionPixelSize(DR.dimen.compose_media_preview_size)
 
@@ -84,8 +107,10 @@ class MediaPreviewAdapter(
     override fun onBindViewHolder(holder: PreviewViewHolder, position: Int) {
         val item = differ.currentList[position]
         holder.progressImageView.setChecked(!item.description.isNullOrEmpty())
-        holder.progressImageView.setProgress(item.uploadPercent)
-        if (item.type == ComposeActivity.QueuedMedia.Type.AUDIO) {
+
+        holder.progressImageView.setResult(item.uploadState)
+
+        if (item.type == QueuedMedia.Type.AUDIO) {
             // TODO: Fancy waveform display?
             holder.progressImageView.setImageResource(R.drawable.ic_music_box_preview_24dp)
         } else {
@@ -114,12 +139,12 @@ class MediaPreviewAdapter(
 
     private val differ = AsyncListDiffer(
         this,
-        object : DiffUtil.ItemCallback<ComposeActivity.QueuedMedia>() {
-            override fun areItemsTheSame(oldItem: ComposeActivity.QueuedMedia, newItem: ComposeActivity.QueuedMedia): Boolean {
+        object : DiffUtil.ItemCallback<QueuedMedia>() {
+            override fun areItemsTheSame(oldItem: QueuedMedia, newItem: QueuedMedia): Boolean {
                 return oldItem.localId == newItem.localId
             }
 
-            override fun areContentsTheSame(oldItem: ComposeActivity.QueuedMedia, newItem: ComposeActivity.QueuedMedia): Boolean {
+            override fun areContentsTheSame(oldItem: QueuedMedia, newItem: QueuedMedia): Boolean {
                 return oldItem == newItem
             }
         },
diff --git a/app/src/main/java/app/pachli/components/compose/MediaUploader.kt b/app/src/main/java/app/pachli/components/compose/MediaUploader.kt
index f0c7b7f53..d5188b59b 100644
--- a/app/src/main/java/app/pachli/components/compose/MediaUploader.kt
+++ b/app/src/main/java/app/pachli/components/compose/MediaUploader.kt
@@ -29,6 +29,7 @@ import app.pachli.BuildConfig
 import app.pachli.R
 import app.pachli.components.compose.ComposeActivity.QueuedMedia
 import app.pachli.components.compose.MediaUploaderError.PrepareMediaError
+import app.pachli.components.compose.UploadState.Uploaded
 import app.pachli.core.common.PachliError
 import app.pachli.core.common.string.randomAlphanumericString
 import app.pachli.core.common.util.formatNumber
@@ -57,6 +58,7 @@ import kotlinx.coroutines.channels.awaitClose
 import kotlinx.coroutines.flow.Flow
 import kotlinx.coroutines.flow.SharingStarted
 import kotlinx.coroutines.flow.callbackFlow
+import kotlinx.coroutines.flow.filter
 import kotlinx.coroutines.flow.first
 import kotlinx.coroutines.flow.flatMapLatest
 import kotlinx.coroutines.flow.flow
@@ -68,18 +70,6 @@ import okio.sink
 import okio.source
 import timber.log.Timber
 
-/**
- * Media that has been fully uploaded to the server and may still be being
- * processed.
- *
- * @property mediaId Server-side identifier for this media item
- * @property processed True if the server has finished processing this media item
- */
-data class UploadedMedia(
-    val mediaId: String,
-    val processed: Boolean,
-)
-
 /**
  * Media that has been prepared for uploading.
  *
@@ -164,44 +154,66 @@ sealed interface MediaUploaderError : PachliError {
         }
     }
 
-    /** [ApiError] wrapper. */
+    /**
+     * An error occurred uploading the media, and there is no remote ID.
+     *
+     * [ApiError] wrapper.
+     */
     @JvmInline
     value class UploadMediaError(private val error: ApiError) : MediaUploaderError, PachliError by error
 
+    /**
+     * An error occurred updating media that has already been uploaded.
+     *
+     * @param serverId Server's ID for the media
+     */
+    data class UpdateMediaError(val serverId: String, val error: ApiError) : MediaUploaderError, PachliError by error
+
     /** Server did return media with ID [uploadId]. */
     data class UploadIdNotFoundError(val uploadId: Int) : MediaUploaderError {
         override val resourceId = R.string.error_media_uploader_upload_not_found_fmt
         override val formatArgs = arrayOf(uploadId.toString())
         override val cause = null
     }
-
-    /** Catch-all for arbitrary throwables */
-    data class ThrowableError(private val throwable: Throwable) : MediaUploaderError {
-        override val resourceId = R.string.error_media_uploader_throwable_fmt
-        override val formatArgs = arrayOf(throwable.localizedMessage ?: "")
-        override val cause = null
-    }
 }
 
-/** Events that happen over the life of a media upload. */
-sealed interface UploadEvent {
+/** State of a media upload. */
+sealed interface UploadState {
     /**
-     * Upload has made progress.
+     * Upload is in progress, but incomplete.
      *
      * @property percentage What percent of the file has been uploaded.
      */
-    data class ProgressEvent(val percentage: Int) : UploadEvent
+    data class Uploading(val percentage: Int) : UploadState
 
-    /**
-     * Upload has finished.
-     *
-     * @property media The uploaded media
-     */
-    data class FinishedEvent(val media: UploadedMedia) : UploadEvent
+    sealed interface Uploaded : UploadState {
+        val serverId: String
+
+        /**
+         * Upload has completed, but the server is still processing the media.
+         *
+         * @property serverId Server-side identifier for this media item
+         */
+        data class Processing(override val serverId: String) : UploadState.Uploaded
+
+        /**
+         * Upload has completed, and the server has processed the media.
+         *
+         * @property serverId Server-side identifier for this media item
+         */
+        data class Processed(override val serverId: String) : UploadState.Uploaded
+
+        /**
+         * Post has been published, editing is impossible.
+         *
+         * @property serverId Server-side identifier for this media item
+         */
+        data class Published(override val serverId: String) : UploadState.Uploaded
+    }
 }
 
 data class UploadData(
-    val flow: Flow<Result<UploadEvent, MediaUploaderError>>,
+    val flow: Flow<Result<UploadState, MediaUploaderError>>,
     val scope: CoroutineScope,
 )
 
@@ -231,28 +243,29 @@ class MediaUploader @Inject constructor(
         return mostRecentId++
     }
 
-    suspend fun getMediaUploadState(localId: Int): Result<UploadEvent.FinishedEvent, MediaUploaderError> {
-        return uploads[localId]?.flow
-            // Can't use filterIsInstance<Ok<UploadEvent.FinishedEvent>> here because the type
-            // inside Ok<...> is erased, so the first Ok<_> result is returned, crashing with a
-            // class cast error if it's a ProgressEvent.
-            // Kotlin doesn't warn about this, see
-            // https://discuss.kotlinlang.org/t/is-as-operators-are-unsafe-for-reified-types/22470
-            ?.first { it.get() is UploadEvent.FinishedEvent } as? Ok<UploadEvent.FinishedEvent>
+    /**
+     * Waits for the upload with [localId] to finish (Ok state is one of the
+     * [Uploaded][UploadState.Uploaded] types), or return an error.
+     */
+    suspend fun waitForUploadToFinish(localId: Int): Result<Uploaded, MediaUploaderError> {
+        return uploads[localId]?.flow?.filter {
+            it.get() is Uploaded || it.get() == null
+        }?.first() as? Result<Uploaded, MediaUploaderError>
             ?: Err(MediaUploaderError.UploadIdNotFoundError(localId))
     }
 
     /**
      * Uploads media.
+     *
      * @param media the media to upload
      * @param instanceInfo info about the current media to make sure the media gets resized correctly
      * @return A Flow emitting upload events.
      * The Flow is hot, in order to cancel upload or clear resources call [cancelUploadScope].
      */
     @OptIn(ExperimentalCoroutinesApi::class)
-    fun uploadMedia(media: QueuedMedia, instanceInfo: InstanceInfo): Flow<Result<UploadEvent, MediaUploaderError>> {
+    fun uploadMedia(media: QueuedMedia, instanceInfo: InstanceInfo): Flow<Result<UploadState, MediaUploaderError>> {
         val uploadScope = CoroutineScope(Dispatchers.IO)
-        val uploadFlow: Flow<Result<UploadEvent, MediaUploaderError>> = flow {
+        val uploadFlow: Flow<Result<UploadState, MediaUploaderError>> = flow {
             if (shouldResizeMedia(media, instanceInfo)) {
                 emit(downsize(media, instanceInfo))
             } else {
@@ -371,7 +384,7 @@ class MediaUploader @Inject constructor(
 
     private val contentResolver = context.contentResolver
 
-    private suspend fun upload(media: QueuedMedia): Flow<Result<UploadEvent, MediaUploaderError.UploadMediaError>> {
+    private suspend fun upload(media: QueuedMedia): Flow<Result<UploadState, MediaUploaderError.UploadMediaError>> {
         return callbackFlow {
             var mimeType = contentResolver.getType(media.uri)
 
@@ -405,7 +418,7 @@ class MediaUploader @Inject constructor(
                 media.mediaSize,
             ) { percentage ->
                 if (percentage != lastProgress) {
-                    trySend(Ok(UploadEvent.ProgressEvent(percentage)))
+                    trySend(Ok(UploadState.Uploading(percentage)))
                 }
                 lastProgress = percentage
             }
@@ -424,7 +437,13 @@ class MediaUploader @Inject constructor(
 
             val uploadResult = mediaUploadApi.uploadMedia(body, description, focus)
                 .mapEither(
-                    { UploadEvent.FinishedEvent(UploadedMedia(it.body.id, it.code == 200)) },
+                    {
+                        if (it.code == 200) {
+                            Uploaded.Processed(it.body.id)
+                        } else {
+                            Uploaded.Processing(it.body.id)
+                        }
+                    },
                     { MediaUploaderError.UploadMediaError(it) },
                 )
             send(uploadResult)
diff --git a/app/src/main/java/app/pachli/components/compose/dialog/CaptionDialog.kt b/app/src/main/java/app/pachli/components/compose/dialog/CaptionDialog.kt
index 1acc3d1b9..c007e5593 100644
--- a/app/src/main/java/app/pachli/components/compose/dialog/CaptionDialog.kt
+++ b/app/src/main/java/app/pachli/components/compose/dialog/CaptionDialog.kt
@@ -68,10 +68,12 @@ class CaptionDialog : DialogFragment() {
         input.requestFocus()
 
         val localId = arguments?.getInt(ARG_LOCAL_ID) ?: error("Missing localId")
+        val serverId = arguments?.getString(ARG_SERVER_ID)
+
         val dialog = AlertDialog.Builder(context)
             .setView(binding.root)
             .setPositiveButton(android.R.string.ok) { _, _ ->
-                listener.onUpdateDescription(localId, input.text.toString())
+                listener.onUpdateDescription(localId, serverId, input.text.toString())
             }
             .setNegativeButton(android.R.string.cancel, null)
             .create()
@@ -125,22 +127,25 @@ class CaptionDialog : DialogFragment() {
     }
 
     interface Listener {
-        fun onUpdateDescription(localId: Int, description: String)
+        fun onUpdateDescription(localId: Int, serverId: String?, description: String)
     }
 
     companion object {
         private const val KEY_DESCRIPTION = "app.pachli.KEY_DESCRIPTION"
+        private const val ARG_LOCAL_ID = "app.pachli.ARG_LOCAL_ID"
+        private const val ARG_SERVER_ID = "app.pachli.ARG_SERVER_ID"
         private const val ARG_EXISTING_DESCRIPTION = "app.pachli.ARG_EXISTING_DESCRIPTION"
         private const val ARG_PREVIEW_URI = "app.pachli.ARG_PREVIEW_URI"
-        private const val ARG_LOCAL_ID = "app.pachli.ARG_LOCAL_ID"
 
         fun newInstance(
             localId: Int,
+            serverId: String? = null,
             existingDescription: String?,
             previewUri: Uri,
         ) = CaptionDialog().apply {
             arguments = bundleOf(
                 ARG_LOCAL_ID to localId,
+                ARG_SERVER_ID to serverId,
                 ARG_EXISTING_DESCRIPTION to existingDescription,
                 ARG_PREVIEW_URI to previewUri,
             )
diff --git a/app/src/main/java/app/pachli/components/compose/view/ProgressImageView.kt b/app/src/main/java/app/pachli/components/compose/view/ProgressImageView.kt
index 1fc2daa19..9e8ac10eb 100644
--- a/app/src/main/java/app/pachli/components/compose/view/ProgressImageView.kt
+++ b/app/src/main/java/app/pachli/components/compose/view/ProgressImageView.kt
@@ -24,12 +24,22 @@ import android.graphics.PorterDuff
 import android.graphics.PorterDuffXfermode
 import android.graphics.RectF
 import android.util.AttributeSet
+import androidx.annotation.OptIn
 import androidx.appcompat.content.res.AppCompatResources
 import app.pachli.R
+import app.pachli.components.compose.MediaUploaderError
+import app.pachli.components.compose.UploadState
 import app.pachli.core.designsystem.R as DR
+import app.pachli.core.ui.makeIcon
 import app.pachli.view.MediaPreviewImageView
 import at.connyduck.sparkbutton.helpers.Utils
+import com.github.michaelbull.result.Ok
+import com.github.michaelbull.result.Result
+import com.github.michaelbull.result.onFailure
+import com.github.michaelbull.result.onSuccess
+import com.google.android.material.badge.ExperimentalBadgeUtils
 import com.google.android.material.color.MaterialColors
+import com.mikepenz.iconics.typeface.library.googlematerial.GoogleMaterial
 
 class ProgressImageView
 @JvmOverloads constructor(
@@ -37,7 +47,7 @@ class ProgressImageView
     attrs: AttributeSet? = null,
     defStyleAttr: Int = 0,
 ) : MediaPreviewImageView(context, attrs, defStyleAttr) {
-    private var progress = -1
+    private var result: Result<UploadState, MediaUploaderError> = Ok(UploadState.Uploading(0))
     private val progressRect = RectF()
     private val biggerRect = RectF()
     private val circlePaint = Paint(Paint.ANTI_ALIAS_FLAG).apply {
@@ -60,14 +70,15 @@ class ProgressImageView
     }
     private val circleRadius = Utils.dpToPx(context, 14)
     private val circleMargin = Utils.dpToPx(context, 14)
+    private val uploadErrorRadius = Utils.dpToPx(context, 24)
 
-    fun setProgress(progress: Int) {
-        this.progress = progress
-        if (progress != -1) {
-            setColorFilter(Color.rgb(123, 123, 123), PorterDuff.Mode.MULTIPLY)
-        } else {
-            clearColorFilter()
-        }
+    private val uploadErrorDrawable = makeIcon(context, GoogleMaterial.Icon.gmd_error, 48).apply {
+        setTint(Color.WHITE)
+    }
+
+    @OptIn(ExperimentalBadgeUtils::class)
+    fun setResult(result: Result<UploadState, MediaUploaderError>) {
+        this.result = result
         invalidate()
     }
 
@@ -82,6 +93,24 @@ class ProgressImageView
 
     override fun onDraw(canvas: Canvas) {
         super.onDraw(canvas)
+
+        result.onSuccess { value ->
+            val percentage = when (value) {
+                is UploadState.Uploading -> value.percentage
+                else -> -1
+            }
+            onDrawSuccess(canvas, percentage)
+        }.onFailure { error ->
+            onDrawError(canvas)
+        }
+    }
+
+    private fun onDrawSuccess(canvas: Canvas, progress: Int) {
+        clearColorFilter()
+        if (progress != -1) {
+            setColorFilter(Color.rgb(123, 123, 123), PorterDuff.Mode.MULTIPLY)
+        }
+
         val angle = progress / 100f * 360 - 90
         val halfWidth = width / 2f
         val halfHeight = height / 2f
@@ -107,4 +136,18 @@ class ProgressImageView
         )
         captionDrawable.draw(canvas)
     }
+
+    private fun onDrawError(canvas: Canvas) {
+        setColorFilter(
+            MaterialColors.getColor(this, androidx.appcompat.R.attr.colorError),
+            PorterDuff.Mode.DARKEN,
+        )
+        uploadErrorDrawable.setBounds(
+            (width / 2) - uploadErrorRadius,
+            (height / 2) - uploadErrorRadius,
+            (width / 2) + uploadErrorRadius,
+            (height / 2) + uploadErrorRadius,
+        )
+        uploadErrorDrawable.draw(canvas)
+    }
 }
diff --git a/app/src/main/java/app/pachli/service/SendStatusService.kt b/app/src/main/java/app/pachli/service/SendStatusService.kt
index 604ab011d..b0b9ab118 100644
--- a/app/src/main/java/app/pachli/service/SendStatusService.kt
+++ b/app/src/main/java/app/pachli/service/SendStatusService.kt
@@ -38,6 +38,8 @@ import app.pachli.core.network.model.Status
 import app.pachli.core.network.retrofit.MastodonApi
 import at.connyduck.calladapter.networkresult.fold
 import com.github.michaelbull.result.getOrElse
+import com.github.michaelbull.result.onFailure
+import com.github.michaelbull.result.onSuccess
 import dagger.hilt.android.AndroidEntryPoint
 import java.io.IOException
 import java.util.Date
@@ -145,14 +147,14 @@ class SendStatusService : Service() {
             // first, wait for media uploads to finish
             val media = statusToSend.media.map { mediaItem ->
                 if (mediaItem.id == null) {
-                    val uploadState = mediaUploader.getMediaUploadState(mediaItem.localId)
+                    val uploadState = mediaUploader.waitForUploadToFinish(mediaItem.localId)
                     val media = uploadState.getOrElse {
                         Timber.w("failed uploading media: %s", it.fmt(this@SendStatusService))
                         failSending(statusId)
                         stopSelfWhenDone()
                         return@launch
-                    }.media
-                    mediaItem.copy(id = media.mediaId, processed = media.processed)
+                    }
+                    mediaItem.copy(id = media.serverId)
                 } else {
                     mediaItem
                 }
@@ -165,15 +167,13 @@ class SendStatusService : Service() {
                     delay(1000L * mediaCheckRetries)
                     media.forEach { mediaItem ->
                         if (!mediaItem.processed) {
-                            when (mastodonApi.getMedia(mediaItem.id!!).code()) {
-                                200 -> mediaItem.processed = true // success
-                                206 -> { } // media is still being processed, continue checking
-                                else -> { // some kind of server error, retrying probably doesn't make sense
+                            mastodonApi.getMedia(mediaItem.id!!)
+                                .onSuccess { mediaItem.processed = it.code == 200 }
+                                .onFailure {
                                     failSending(statusId)
                                     stopSelfWhenDone()
                                     return@launch
                                 }
-                            }
                         }
                     }
                     mediaCheckRetries++
@@ -190,13 +190,11 @@ class SendStatusService : Service() {
                 media.forEach { mediaItem ->
                     if (mediaItem.processed && (mediaItem.description != null || mediaItem.focus != null)) {
                         mastodonApi.updateMedia(mediaItem.id!!, mediaItem.description, mediaItem.focus?.toMastodonApiString())
-                            .fold({
-                            }, { throwable ->
-                                Timber.w(throwable, "failed to update media on status send")
-                                failOrRetry(throwable, statusId)
-
+                            .onFailure { error ->
+                                Timber.w("failed to update media on status send: %s", error)
+                                failOrRetry(error.throwable, statusId)
                                 return@launch
-                            })
+                            }
                     }
                 }
             }
diff --git a/app/src/main/res/values-ar/strings.xml b/app/src/main/res/values-ar/strings.xml
index 13413675e..1d96dca87 100644
--- a/app/src/main/res/values-ar/strings.xml
+++ b/app/src/main/res/values-ar/strings.xml
@@ -590,7 +590,6 @@
     <string name="ui_error_bookmark_fmt">%1$s :فشل إجراء إضافة المنشور إلى الفواصل المرجعية</string>
     <string name="notification_unknown_name">غير معروف</string>
     <string name="pref_update_notification_frequency_always">دائما</string>
-    <string name="error_media_upload_sending_fmt">اخفق التحميل: %s</string>
     <string name="pref_update_notification_frequency_never">أبدًا</string>
     <string name="filter_keyword_display_format">%s (الكلمةكاملة)</string>
     <string name="filter_keyword_addition_title">إضافة كلمة مفتاحية</string>
diff --git a/app/src/main/res/values-cy/strings.xml b/app/src/main/res/values-cy/strings.xml
index 04aa7d577..c20211857 100644
--- a/app/src/main/res/values-cy/strings.xml
+++ b/app/src/main/res/values-cy/strings.xml
@@ -612,8 +612,7 @@
 \nHwn yw <a href="https://github.com/mastodon/mastodon/issues/25398">mater Mastodon #25398</a>.</string>
     <string name="load_newest_notifications">Llwytho hysbysiadau diweddaraf</string>
     <string name="compose_delete_draft">Dileu\'r drafft\?</string>
-    <string name="error_media_upload_sending_fmt">Methodd y lanlwytho: %s</string>
     <string name="error_media_playback">Methodd chwarae: %s</string>
     <string name="dialog_delete_filter_positive_action">Dileu</string>
     <string name="dialog_delete_filter_text">Dileu\'r hidlydd \'%1$s\'\?</string>
-</resources>
\ No newline at end of file
+</resources>
diff --git a/app/src/main/res/values-de/strings.xml b/app/src/main/res/values-de/strings.xml
index 9cb620a81..20ab7351e 100644
--- a/app/src/main/res/values-de/strings.xml
+++ b/app/src/main/res/values-de/strings.xml
@@ -568,7 +568,6 @@
     <string name="error_missing_edits">Deinem Server ist bekannt, dass dieser Beitrag bearbeitet wurde. Allerdings besitzt er keine Kopien der Änderungen, weshalb diese nicht angezeigt werden können.
 \n
 \nHierbei handelt es sich um <a href="https://github.com/mastodon/mastodon/issues/25398">Mastodon Issue #25398</a>.</string>
-    <string name="error_media_upload_sending_fmt">Das Hochladen ist fehlgeschlagen: %s</string>
     <string name="ui_error_translate_status_fmt">Übersetzung fehlgeschlagen: %1$s</string>
     <string name="update_dialog_negative">Erinnere mich nie</string>
     <string name="translating">Übersetze…</string>
@@ -603,4 +602,4 @@
     <string name="reaction_name_and_count">%1$s %2$d</string>
     <string name="announcement_date">%1$s %2$s</string>
     <string name="announcement_date_updated">(Aktualisiert: %1$s)</string>
-</resources>
\ No newline at end of file
+</resources>
diff --git a/app/src/main/res/values-el/strings.xml b/app/src/main/res/values-el/strings.xml
index fb8a54a90..23cff3b44 100644
--- a/app/src/main/res/values-el/strings.xml
+++ b/app/src/main/res/values-el/strings.xml
@@ -93,7 +93,6 @@
     <string name="dialog_redraft_post_warning">Διαγραφή και αναδιατύπωση αυτής της δημοσίευσης;</string>
     <string name="error_following_hashtag_format">Σφάλμα ακολουθίας #%s</string>
     <string name="error_unfollowing_hashtag_format">Σφάλμα μη-ακολουθίας #%s</string>
-    <string name="error_media_upload_sending_fmt">Το ανέβασμα απέτυχε: %s</string>
     <string name="error_media_upload_sending">Το ανέβασμα αρχείου απέτυχε.</string>
     <string name="title_home">Αρχική Σελίδα</string>
     <string name="error_sender_account_gone">Σφάλμα αποστολής ανάρτησης.</string>
diff --git a/app/src/main/res/values-en-rGB/strings.xml b/app/src/main/res/values-en-rGB/strings.xml
index b4e93da78..fa8c0aaf2 100644
--- a/app/src/main/res/values-en-rGB/strings.xml
+++ b/app/src/main/res/values-en-rGB/strings.xml
@@ -59,7 +59,6 @@
     <string name="error_following_hashtags_unsupported">This instance does not support following hashtags.</string>
     <string name="title_edits">Edits</string>
     <string name="title_followed_hashtags">Followed hashtags</string>
-    <string name="error_media_upload_sending_fmt">The upload failed: %s</string>
     <string name="title_migration_relogin">Re-login for push notifications</string>
     <string name="title_drafts">Drafts</string>
     <string name="title_tab_public_trending_statuses">Posts</string>
@@ -69,4 +68,4 @@
     <string name="title_tab_public_trending_hashtags">Hashtags</string>
     <string name="error_muting_hashtag_format">Error muting #%s</string>
     <string name="title_scheduled_posts">Scheduled posts</string>
-</resources>
\ No newline at end of file
+</resources>
diff --git a/app/src/main/res/values-es/strings.xml b/app/src/main/res/values-es/strings.xml
index e1f2790c7..2a7b071ca 100644
--- a/app/src/main/res/values-es/strings.xml
+++ b/app/src/main/res/values-es/strings.xml
@@ -592,7 +592,6 @@
     <string name="load_newest_statuses">Cargar las publicaciones más nuevas</string>
     <string name="dialog_save_profile_changes_message">¿Quieres guardar tus cambios de perfil?</string>
     <string name="pref_update_notification_frequency_always">Siempre</string>
-    <string name="error_media_upload_sending_fmt">La carga falló: %s</string>
     <string name="pref_update_notification_frequency_never">Nunca</string>
     <string name="pref_title_show_self_boosts_description">Alguien impulsa su propia publicación</string>
     <string name="ui_error_filter_v1_load_fmt">La carga de filtros falló: %1$s</string>
@@ -655,7 +654,6 @@
     <string name="compose_warn_language_dialog_fmt">El idioma de la publicación está configurado en %1$s, pero es posible que la hayas escrito en %2$s.</string>
     <string name="error_prepare_media_unsupported_mime_type_fmt">el servidor no es compatible con el tipo de archivo: %1$s</string>
     <string name="error_pick_media_fmt">No se pudo adjuntar el archivo a la publicación: %1$s</string>
-    <string name="error_media_uploader_throwable_fmt">%1$s</string>
     <string name="error_prepare_media_content_resolver_missing_path_fmt">al agente de resolución de contenido le faltó una ruta: %1$s</string>
     <string name="error_prepare_media_content_resolver_unsupported_scheme_fmt">el agente de resolución de contenido tiene un esquema no compatible: %1$s</string>
     <string name="error_prepare_media_file_is_too_large_fmt">el tamaño del archivo es %1$s, el máximo permitido es %2$s</string>
@@ -791,4 +789,4 @@
     <string name="conversation_0_recipients">Ningún participante más</string>
     <string name="pref_title_confirm_status_language">Revisar idioma de la publicación antes de publicar</string>
     <string name="compose_warn_language_dialog_accept_and_dont_ask_fmt">Publicar como está (%1$s) y no volver a preguntar</string>
-</resources>
\ No newline at end of file
+</resources>
diff --git a/app/src/main/res/values-fa/strings.xml b/app/src/main/res/values-fa/strings.xml
index 6125ad8ba..4a3ba6808 100644
--- a/app/src/main/res/values-fa/strings.xml
+++ b/app/src/main/res/values-fa/strings.xml
@@ -568,8 +568,7 @@
     <string name="notification_listenable_worker_description">آگاهی‌ها هنگامی که تاسکی در پس‌زمینه کار می‌کند</string>
     <string name="notification_notification_worker">واکشی آگاهی‌ها…</string>
     <string name="notification_prune_cache">نگه‌داری انباره…</string>
-    <string name="error_media_upload_sending_fmt">بارگذاری شکست خورد: %s</string>
     <string name="error_media_playback">پخش شکست خورد: %s</string>
     <string name="dialog_delete_filter_positive_action">حذف</string>
     <string name="dialog_delete_filter_text">«%1$s» حذف پالایهٔ ؟</string>
-</resources>
\ No newline at end of file
+</resources>
diff --git a/app/src/main/res/values-fi/strings.xml b/app/src/main/res/values-fi/strings.xml
index 10d1f929e..021fee357 100644
--- a/app/src/main/res/values-fi/strings.xml
+++ b/app/src/main/res/values-fi/strings.xml
@@ -300,7 +300,6 @@
     <string name="confirmation_unblocked">Käyttäjän esto poistettu</string>
     <string name="title_edits">Muokkaukset</string>
     <string name="title_followed_hashtags">Seuratut aihetunnisteet</string>
-    <string name="error_media_upload_sending_fmt">Lataus epäonnistui: %s</string>
     <string name="add_account_description">Lisää uusi Mastodon-tili</string>
     <string name="dialog_title_finishing_media_upload">Mediatiedoston latausta viimeistellään</string>
     <string name="pref_title_show_self_boosts_description">Joku tehostaa omaa julkaisuaan</string>
@@ -631,7 +630,6 @@
     <string name="compose_warn_language_dialog_change_language_fmt">Merkitse kieleksi %1$s ja julkaise</string>
     <string name="compose_warn_language_dialog_accept_language_fmt">Julkaise muuttamattomana (%1$s)</string>
     <string name="error_media_uploader_upload_not_found_fmt">medialatausta nimeltä %1$s ei löydy</string>
-    <string name="error_media_uploader_throwable_fmt">%1$s</string>
     <string name="error_prepare_media_content_resolver_missing_path_fmt">sisällönselvittäjä-URI:ltä puuttui polku: %1$s</string>
     <string name="error_prepare_media_io_fmt">%1$s</string>
     <string name="error_prepare_media_file_is_too_large_fmt">tiedoston koko on %1$s, suurin sallittu on %2$s</string>
@@ -776,4 +774,4 @@
     <string name="pref_title_confirm_status_language">Tarkasta julkaisun kieli ennen julkaisemista</string>
     <string name="action_copy_item">Kopioi kohde</string>
     <string name="item_copied">Teksti kopioitu</string>
-</resources>
\ No newline at end of file
+</resources>
diff --git a/app/src/main/res/values-fr/strings.xml b/app/src/main/res/values-fr/strings.xml
index 9474832d4..2583ec884 100644
--- a/app/src/main/res/values-fr/strings.xml
+++ b/app/src/main/res/values-fr/strings.xml
@@ -572,7 +572,6 @@
     <string name="filter_edit_keyword_title">Modifier mot-clé</string>
     <string name="filter_description_format">%s : %s</string>
     <string name="action_translate_undo">Annuler la traduction</string>
-    <string name="error_media_upload_sending_fmt">Le téléversement a échoué : %s</string>
     <string name="title_public_trending_statuses">Publications en tendance</string>
     <string name="title_tab_public_trending_hashtags">Hashtags</string>
     <string name="action_translate">Traduire</string>
@@ -607,4 +606,4 @@
     <string name="notification_notification_worker">Récupération des notifications …</string>
     <string name="notification_prune_cache">Maintenance du cache …</string>
     <string name="announcement_date">%1$s %2$s</string>
-</resources>
\ No newline at end of file
+</resources>
diff --git a/app/src/main/res/values-gd/strings.xml b/app/src/main/res/values-gd/strings.xml
index 5eda9973b..7acce2ba0 100644
--- a/app/src/main/res/values-gd/strings.xml
+++ b/app/src/main/res/values-gd/strings.xml
@@ -583,5 +583,4 @@
     <string name="notification_listenable_worker_description">Brathan nuair a bhios Pachli ag obair sa chùlaibh</string>
     <string name="notification_notification_worker">A’ faighinn nam brathan…</string>
     <string name="notification_prune_cache">Obair-ghlèidhidh air an tasgadan…</string>
-    <string name="error_media_upload_sending_fmt">Dh’fhàillig leis an luchdadh suas: %s</string>
-</resources>
\ No newline at end of file
+</resources>
diff --git a/app/src/main/res/values-gl/strings.xml b/app/src/main/res/values-gl/strings.xml
index bebd7cbf5..4c7ef1d9a 100644
--- a/app/src/main/res/values-gl/strings.xml
+++ b/app/src/main/res/values-gl/strings.xml
@@ -561,7 +561,6 @@
     <string name="notification_listenable_worker_description">Notificacións cando Pachli está a funcionar en segundo plano</string>
     <string name="notification_notification_worker">Obtendo as notificacións…</string>
     <string name="notification_prune_cache">Mantemento da caché…</string>
-    <string name="error_media_upload_sending_fmt">Fallou a subida: %s</string>
     <string name="dialog_delete_filter_positive_action">Eliminar</string>
     <string name="dialog_delete_filter_text">Eliminar o filtro \'%1$s\'\?</string>
     <string name="pref_title_show_self_boosts">Mostrar autopromocións</string>
@@ -628,7 +627,6 @@
     <string name="compose_warn_language_dialog_change_language_fmt">Cambiar o idioma a %1$s e publicar</string>
     <string name="error_media_uploader_upload_not_found_fmt">non se atopou o multimedia subido con ID %1$s</string>
     <string name="compose_warn_language_dialog_accept_language_fmt">Publicar tal como está (%1$s)</string>
-    <string name="error_media_uploader_throwable_fmt">%1$s</string>
     <string name="error_prepare_media_content_resolver_missing_path_fmt">ao resolutor da URI do contido fáltalle unha ruta: %1$s</string>
     <string name="error_prepare_media_io_fmt">%1$s</string>
     <string name="error_prepare_media_content_resolver_unsupported_scheme_fmt">o resolutor da URI do cotido non é compatible co esquema: %1$s</string>
@@ -770,4 +768,4 @@
     <string name="pref_notification_fetch_ok_timestamp_fmt">✔ hai %1$s @ %2$s</string>
     <string name="pref_notification_fetch_err_timestamp_fmt">✖ hai %1$s @ %2$s</string>
     <string name="pref_notification_fetch_needs_push">A conta non ten o método «push». Pechar a sesión e volver acceder podería arranxalo.</string>
-</resources>
\ No newline at end of file
+</resources>
diff --git a/app/src/main/res/values-in/strings.xml b/app/src/main/res/values-in/strings.xml
index 449b7d2cc..4ef94cd85 100644
--- a/app/src/main/res/values-in/strings.xml
+++ b/app/src/main/res/values-in/strings.xml
@@ -210,7 +210,6 @@
     <string name="title_public_trending_statuses">Postingan trending</string>
     <string name="title_edits">Sunting</string>
     <string name="title_followed_hashtags">Tagar yang diikuti</string>
-    <string name="error_media_upload_sending_fmt">Upload gagal: %s</string>
     <string name="title_tab_public_trending_statuses">Postingan</string>
     <string name="title_tab_public_trending_hashtags">Tagar</string>
     <string name="notification_header_report_format">%s dilaporkan %s</string>
diff --git a/app/src/main/res/values-it/strings.xml b/app/src/main/res/values-it/strings.xml
index f8c3973ae..c865b62a8 100644
--- a/app/src/main/res/values-it/strings.xml
+++ b/app/src/main/res/values-it/strings.xml
@@ -606,9 +606,8 @@
     <string name="update_dialog_neutral">Non ricordarmelo per questa versione</string>
     <string name="pref_title_update_settings">Aggiornamenti Software</string>
     <string name="pref_update_notification_frequency_always">Sempre</string>
-    <string name="error_media_upload_sending_fmt">Il caricamento è fallito: %s</string>
     <string name="pref_update_notification_frequency_never">Mai</string>
     <string name="title_tab_public_trending_statuses">Post</string>
     <string name="pref_update_notification_frequency_once_per_version">Una volta per versione</string>
     <string name="update_dialog_title">Un aggiornamento è disponibile</string>
-</resources>
\ No newline at end of file
+</resources>
diff --git a/app/src/main/res/values-ja/strings.xml b/app/src/main/res/values-ja/strings.xml
index 702ce7537..4dfe883e9 100644
--- a/app/src/main/res/values-ja/strings.xml
+++ b/app/src/main/res/values-ja/strings.xml
@@ -551,7 +551,6 @@
     <string name="load_newest_notifications">最新の通知を読み込む</string>
     <string name="compose_delete_draft">下書きを削除しますか？</string>
     <string name="error_list_load">リストを読み込む際のエラー</string>
-    <string name="error_media_upload_sending_fmt">アップロードに失敗しました: %s</string>
     <string name="error_missing_edits">あなたのサーバーは、この投稿が変更されたことを把握していますが、編集履歴のコピーを備えていないので、表示できません。
 \n
 \nこれは<a href="https://github.com/mastodon/mastodon/issues/25398">Mastodonのissue #25398</a>です。</string>
@@ -595,4 +594,4 @@
     <string name="action_translate">翻訳</string>
     <string name="update_dialog_title">アップデート可能です</string>
     <string name="action_translate_undo">翻訳を元に戻す</string>
-</resources>
\ No newline at end of file
+</resources>
diff --git a/app/src/main/res/values-kab/strings.xml b/app/src/main/res/values-kab/strings.xml
index bcd780893..ce401d692 100644
--- a/app/src/main/res/values-kab/strings.xml
+++ b/app/src/main/res/values-kab/strings.xml
@@ -277,7 +277,6 @@
     <string name="duration_indefinite">War talast</string>
     <string name="action_subscribe_account">Ḍfeṛ</string>
     <string name="report_category_other">Wayeḍ</string>
-    <string name="error_media_uploader_throwable_fmt">%1$s</string>
     <string name="search_operator_attachment_dialog_video_label">Tavidyutt</string>
     <string name="search_operator_language_checked_fmt">%1$s</string>
     <string name="post_media_image">Tugna</string>
diff --git a/app/src/main/res/values-my/strings.xml b/app/src/main/res/values-my/strings.xml
index 9c692fe72..46d127edc 100644
--- a/app/src/main/res/values-my/strings.xml
+++ b/app/src/main/res/values-my/strings.xml
@@ -7,7 +7,6 @@
     <string name="error_media_upload_type">ဤဖိုင်အမျိုးအစားကိုမတင်နိုင်ပါ။</string>
     <string name="error_media_upload_opening">ဤဖိုင်ကိုမဖွင့်နိုင်ပါ။</string>
     <string name="error_media_upload_image_or_video">ရုပ်ပုံနှင့်ဗီဒီယိုများအား ပိုစ့်တစ်ခုတည်းတွင် ယှဥ်တွဲမတင်နိုင်ပါ။</string>
-    <string name="error_media_upload_sending_fmt">တင်ခြင်းမအောင်မြင်ပါ။: %s</string>
     <string name="error_sender_account_gone">ပိုစ့်တင်ရာ၌ချို့ယွင်းမှု။</string>
     <string name="error_following_hashtag_format">စောင့်ကြည့်ရာ၌ ချို့ယွင်းမှု #%s</string>
     <string name="error_muting_hashtag_format">Mute လုပ်ရာ၌ ချို့ယွင်းချက် #%s</string>
@@ -103,4 +102,4 @@
     <string name="action_post_failed_detail_plural">ပိုစ့်တင်ခြင်းမအောင်မြင်ပါ ပုံကြမ်းများထဲတွင်သိမ်းထားသည်။\n\nဆာဗာအားမချိတ်ဆက်နိုင်ခြင်း သို့ ပယ်ချခြင်းဖြစ်နိုင်သည်။</string>
     <string name="action_post_failed_detail">ပိုစ့်တင်ခြင်းမအောင်မြင်ပါ ပုံကြမ်းများထဲတွင်သိမ်းထားသည်။\n\nဆာဗာအားမချိတ်ဆက်နိုင်ခြင်း သို့ ပယ်ချခြင်းဖြစ်နိုင်သည်။</string>
     <string name="action_block">ဘလော့ခ်</string>
-</resources>
\ No newline at end of file
+</resources>
diff --git a/app/src/main/res/values-nb-rNO/strings.xml b/app/src/main/res/values-nb-rNO/strings.xml
index c043ac0de..a7b0f5fc1 100644
--- a/app/src/main/res/values-nb-rNO/strings.xml
+++ b/app/src/main/res/values-nb-rNO/strings.xml
@@ -575,7 +575,6 @@
     <string name="title_lists_failed">Lister - kunne ikke lastes inn</string>
     <string name="manage_lists">Håndter lister</string>
     <string name="compose_schedule_date_time_fmt">%1$s %2$s</string>
-    <string name="error_media_upload_sending_fmt">Mislyktes ved opplasting: %s</string>
     <string name="title_public_trending_links">Trendende lenker</string>
     <string name="title_tab_public_trending_hashtags">Emneknagger</string>
     <string name="title_tab_public_trending_links">Lenker</string>
@@ -586,7 +585,6 @@
     <string name="compose_warn_language_dialog_fmt">Språket til innlegget er %1$s men det kan skje at du har skrevet innlegget på %2$s.</string>
     <string name="compose_warn_language_dialog_change_language_fmt">Byt språk til %1$s og tut</string>
     <string name="error_media_uploader_upload_not_found_fmt">Mediaopplasting med ID %1$s finnes ikke</string>
-    <string name="error_media_uploader_throwable_fmt">%1$s</string>
     <string name="ui_error_translate_status_fmt">Oversettelse mislyktes: %1$s</string>
     <string name="ui_error_filter_v1_load_fmt">Å laste inn filtere mislyktes: %1$s</string>
     <string name="notification_severed_relationships_account_suspension_body">En moderator suspenderte kontoen</string>
@@ -772,4 +770,4 @@
     <string name="search_operator_where_dialog_all">Alle innlegg</string>
     <string name="search_operator_where_dialog_library_hint">Dine egne innlegg, fremhevinger, favoritmerker, bokmerker, og innlegg som @nevner deg</string>
     <string name="search_operator_where_dialog_public">Fødererte innlegg</string>
-</resources>
\ No newline at end of file
+</resources>
diff --git a/app/src/main/res/values-nl/strings.xml b/app/src/main/res/values-nl/strings.xml
index 90778f370..847e78122 100644
--- a/app/src/main/res/values-nl/strings.xml
+++ b/app/src/main/res/values-nl/strings.xml
@@ -549,7 +549,6 @@
     <string name="notification_notification_worker">Meldingen ophalen…</string>
     <string name="notification_listenable_worker_name">Achtergrond activiteit</string>
     <string name="notification_listenable_worker_description">Meldingen als Pachli werkt op de achtergrond</string>
-    <string name="error_media_upload_sending_fmt">De upload is mislukt: %s</string>
     <string name="socket_timeout_exception">Contact zoeken met je server duurde te lang</string>
     <string name="dialog_delete_filter_positive_action">Verwijder</string>
     <string name="dialog_delete_filter_text">Verwijder filter \'%1$s\'\?</string>
@@ -608,4 +607,4 @@
     <string name="pref_update_check_no_updates">Er zijn geen updates beschikbaar</string>
     <string name="pref_update_next_scheduled_check">Volgende geplande controle: %1$s</string>
     <string name="pref_summary_content_filters">Je server ondersteund geen filters</string>
-</resources>
\ No newline at end of file
+</resources>
diff --git a/app/src/main/res/values-oc/strings.xml b/app/src/main/res/values-oc/strings.xml
index 619326ce3..c005db416 100644
--- a/app/src/main/res/values-oc/strings.xml
+++ b/app/src/main/res/values-oc/strings.xml
@@ -568,5 +568,4 @@
     <string name="notification_listenable_worker_description">Notificacions quand Tuska s’executa en rèireplan</string>
     <string name="notification_notification_worker">Recuperacion de las notificacions…</string>
     <string name="notification_prune_cache">Manteniment del cache…</string>
-    <string name="error_media_upload_sending_fmt">Fracàs del mandadís : %s</string>
-</resources>
\ No newline at end of file
+</resources>
diff --git a/app/src/main/res/values-pt-rBR/strings.xml b/app/src/main/res/values-pt-rBR/strings.xml
index 161bbdc28..8dbfdb762 100644
--- a/app/src/main/res/values-pt-rBR/strings.xml
+++ b/app/src/main/res/values-pt-rBR/strings.xml
@@ -557,7 +557,6 @@
     <string name="notification_unknown_name">Desconhecido</string>
     <string name="total_usage">Uso total</string>
     <string name="pref_update_notification_frequency_always">Sempre</string>
-    <string name="error_media_upload_sending_fmt">O carregamento falhou: %s</string>
     <string name="pref_update_notification_frequency_never">Nunca</string>
     <string name="filter_keyword_display_format">%s (palavra inteira)</string>
     <string name="filter_keyword_addition_title">Adicionar palavra-chave</string>
@@ -614,4 +613,4 @@
     <string name="load_newest_notifications">Carregar notificações mais recentes</string>
     <string name="action_discard">Descartar mudanças</string>
     <string name="pref_ui_text_size">Tamanho do texto da UI</string>
-</resources>
\ No newline at end of file
+</resources>
diff --git a/app/src/main/res/values-sv/strings.xml b/app/src/main/res/values-sv/strings.xml
index 45e395693..a3577e65a 100644
--- a/app/src/main/res/values-sv/strings.xml
+++ b/app/src/main/res/values-sv/strings.xml
@@ -593,7 +593,6 @@
     <string name="load_newest_statuses">Ladda de nyaste inläggen</string>
     <string name="dialog_save_profile_changes_message">Vill du spara dina profiländringar?</string>
     <string name="pref_update_notification_frequency_always">Alltid</string>
-    <string name="error_media_upload_sending_fmt">Uppladdning misslyckades: %s</string>
     <string name="pref_update_notification_frequency_never">Aldrig</string>
     <string name="pref_title_show_self_boosts_description">Någon som knuffar sin toot</string>
     <string name="ui_error_filter_v1_load_fmt">Laddning av filter misslyckades: %1$s</string>
@@ -611,4 +610,4 @@
     <string name="action_translate_undo">Ångra översättning</string>
     <string name="server_repository_error">Kunde inte hämta serverinformation för %1$s: %2$s</string>
     <string name="pref_summary_content_filters">Din server stöder inte filter</string>
-</resources>
\ No newline at end of file
+</resources>
diff --git a/app/src/main/res/values-tr/strings.xml b/app/src/main/res/values-tr/strings.xml
index 1866a3224..2cf25a225 100644
--- a/app/src/main/res/values-tr/strings.xml
+++ b/app/src/main/res/values-tr/strings.xml
@@ -568,6 +568,5 @@
     <string name="error_missing_edits">Sunucunuz bu gönderinin düzenlendiğini bilir, ancak düzenlemelerin bir kopyası yoktur, bu nedenle bunlar size gösterilemez.
 \n
 \nBu <a href="https://github.com/mastodon/mastodon/issues/25398">Mastodon sorununu #25398</a>.</string>
-    <string name="error_media_upload_sending_fmt">Yükleme başarısız oldu: %s</string>
     <string name="error_media_playback">Oynatma başarısız oldu: %s</string>
-</resources>
\ No newline at end of file
+</resources>
diff --git a/app/src/main/res/values-uk/strings.xml b/app/src/main/res/values-uk/strings.xml
index 4a46d4a46..df7387883 100644
--- a/app/src/main/res/values-uk/strings.xml
+++ b/app/src/main/res/values-uk/strings.xml
@@ -583,5 +583,4 @@
     <string name="error_missing_edits">Ваш сервер знає, що цей допис було змінено, але не має копії редагувань, тому вони не можуть бути вам показані.
 \n
 \nЦе <a href="https://github.com/mastodon/mastodon/issues/25398">помилка #25398 у Mastodon</a>.</string>
-    <string name="error_media_upload_sending_fmt">Не вдалося вивантажити: %s</string>
-</resources>
\ No newline at end of file
+</resources>
diff --git a/app/src/main/res/values-vi/strings.xml b/app/src/main/res/values-vi/strings.xml
index e46fc4655..59a6c6efd 100644
--- a/app/src/main/res/values-vi/strings.xml
+++ b/app/src/main/res/values-vi/strings.xml
@@ -551,8 +551,7 @@
     <string name="notification_listenable_worker_description">Thông báo khi Pachli hoạt động ngầm</string>
     <string name="notification_notification_worker">Đang nạp thông báo…</string>
     <string name="notification_prune_cache">Bảo trì bộ nhớ đệm…</string>
-    <string name="error_media_upload_sending_fmt">Không thể tải lên: %s</string>
     <string name="error_media_playback">Không thể phát: %s</string>
     <string name="dialog_delete_filter_text">Xóa bộ lọc \'%1$s\'\?</string>
     <string name="dialog_delete_filter_positive_action">Xóa</string>
-</resources>
\ No newline at end of file
+</resources>
diff --git a/app/src/main/res/values-zh-rCN/strings.xml b/app/src/main/res/values-zh-rCN/strings.xml
index abd31fbeb..8f2cd4322 100644
--- a/app/src/main/res/values-zh-rCN/strings.xml
+++ b/app/src/main/res/values-zh-rCN/strings.xml
@@ -565,8 +565,7 @@
     <string name="notification_notification_worker">获取通知中…</string>
     <string name="notification_prune_cache">缓存维护…</string>
     <string name="notification_listenable_worker_name">后台活动</string>
-    <string name="error_media_upload_sending_fmt">上传失败了：%s</string>
     <string name="error_media_playback">播放失败了：%s</string>
     <string name="dialog_delete_filter_text">删除筛选器\'%1$s\'吗？</string>
     <string name="dialog_delete_filter_positive_action">删除</string>
-</resources>
\ No newline at end of file
+</resources>
diff --git a/app/src/main/res/values/strings.xml b/app/src/main/res/values/strings.xml
index 9458afe24..1d65488e9 100644
--- a/app/src/main/res/values/strings.xml
+++ b/app/src/main/res/values/strings.xml
@@ -27,7 +27,6 @@
     <string name="error_media_download_permission">Permission to store media is required.</string>
     <string name="error_media_upload_image_or_video">images and videos cannot both be attached to the same post.</string>
     <string name="error_media_upload_sending">The upload failed.</string>
-    <string name="error_media_upload_sending_fmt">The upload failed: %s</string>
     <string name="error_sender_account_gone">Error sending post.</string>
     <string name="error_following_hashtag_format">Error following #%s</string>
     <string name="error_unfollowing_hashtag_format">Error unfollowing #%s</string>
@@ -397,7 +396,7 @@
     <string name="lock_account_label_description">Requires you to manually approve followers</string>
     <string name="compose_delete_draft">Delete draft?</string>
     <string name="compose_save_draft">Save draft?</string>
-    <string name="compose_save_draft_loses_media">Save draft? (Attachments will be uploaded again when you restore the draft.)</string>
+    <string name="compose_save_draft_loses_media">Attachments will be uploaded again when you restore the draft.</string>
     <string name="unsaved_changes">You have unsaved changes.</string>
     <string name="send_post_notification_title">Sending post…</string>
     <string name="send_post_notification_error_title">Error sending post</string>
@@ -721,7 +720,6 @@
     <string name="compose_warn_language_dialog_accept_and_dont_ask_fmt">Post as-is (%1$s) and don\'t ask again</string>
 
     <string name="error_media_uploader_upload_not_found_fmt">media upload with ID %1$s not found</string>
-    <string name="error_media_uploader_throwable_fmt">%1$s</string>
 
     <string name="error_prepare_media_content_resolver_missing_path_fmt">content resolver URI was missing a path: %1$s</string>
     <string name="error_prepare_media_content_resolver_unsupported_scheme_fmt">content resolver URI has unsupported scheme: %1$s</string>
@@ -853,4 +851,7 @@
 
     <string name="action_copy_item">Copy item</string>
     <string name="item_copied">Text copied</string>
+
+    <string name="upload_failed_msg_fmt">The upload will be retried when you send the post. If it fails again the post will be saved in your drafts.\n\nThe error was: %1$s</string>
+    <string name="upload_failed_modify_attachment">Modify attachment</string>
 </resources>
diff --git a/core/network/src/main/kotlin/app/pachli/core/network/retrofit/MastodonApi.kt b/core/network/src/main/kotlin/app/pachli/core/network/retrofit/MastodonApi.kt
index e03245664..8ac6510eb 100644
--- a/core/network/src/main/kotlin/app/pachli/core/network/retrofit/MastodonApi.kt
+++ b/core/network/src/main/kotlin/app/pachli/core/network/retrofit/MastodonApi.kt
@@ -201,14 +201,14 @@ interface MastodonApi {
     @PUT("api/v1/media/{mediaId}")
     suspend fun updateMedia(
         @Path("mediaId") mediaId: String,
-        @Field("description") description: String?,
-        @Field("focus") focus: String?,
-    ): NetworkResult<Attachment>
+        @Field("description") description: String? = null,
+        @Field("focus") focus: String? = null,
+    ): ApiResult<Attachment>
 
     @GET("api/v1/media/{mediaId}")
     suspend fun getMedia(
         @Path("mediaId") mediaId: String,
-    ): Response<MediaUploadResult>
+    ): ApiResult<MediaUploadResult>
 
     @POST("api/v1/statuses")
     suspend fun createStatus(
diff --git a/core/network/src/main/res/values/strings.xml b/core/network/src/main/res/values/strings.xml
index 6ecb876d1..ac5f6a2c0 100644
--- a/core/network/src/main/res/values/strings.xml
+++ b/core/network/src/main/res/values/strings.xml
@@ -21,8 +21,8 @@
     <string name="node_info_error_no_software_version">software version is missing, empty, or blank</string>
 
     <string name="server_error_unparseable_version">could not parse \"%1$s\" as a version: %2$s</string>
-    <string name="error_generic_fmt">An error occurred: %s</string>
-    <string name="error_404_not_found_fmt">Your server does not support this feature: %1$s</string>
+    <string name="error_generic_fmt">%1$s</string>
+    <string name="error_404_not_found_fmt">your server does not support this feature: %1$s</string>
     <string name="error_429_rate_limit_fmt">your server is rate-limiting your requests: %1$s</string>
     <string name="error_json_data_fmt">Your server returned an invalid response: %1$s</string>
     <string name="error_network_fmt">A network error occurred: %s</string>