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A claim lives or dies on its documentation, and documentation now means phone photos and video. The problem is that the systems receiving them were often sized for a handful of small JPEGs, while the phone in your pocket produces files an order of magnitude larger.
So you end up with the worst possible combination: the evidence is good, and it won't go through.
Why the Upload Fails
Almost always one of three things:
- A per-file or per-session size cap. Claim portals commonly cap uploads well below what a modern phone produces.
- A file-count limit. Some portals accept only a few attachments at a time, which is awkward when thorough documentation means forty photos.
- A timeout. Large uploads over a weak connection — often exactly the situation after storm damage — fail partway and report a generic error.
For scale: a photo from a recent iPhone or Android flagship is typically 3–5MB, and 4K video runs on the order of 350MB per minute. A careful walkthrough — thirty photos plus a two-minute video — can approach a gigabyte. If your adjuster asked you to email it, that will bounce; consumer email caps out around 20–25MB per message, and less once encoding overhead is counted.
Document It Properly First
Before worrying about delivery, make sure you've captured enough. You can't re-photograph damage after a repair, and the gaps are what get queried later.
Work in three ranges:
- Wide — the whole room or the property from the street, establishing context and location.
- Mid — each damaged area in relation to its surroundings, so the damage is locatable.
- Close — the specific damage, close enough to show detail like cracking, staining or warping.
Then add the things people forget: model and serial plates on any appliance, HVAC unit or electronics being claimed; undamaged areas of the same material for comparison; and a shot showing the source of the damage where it's visible, such as the failed pipe or the missing shingles.
A slow video walkthrough narrating what you're seeing is genuinely useful alongside stills. It establishes spatial relationships that individual photos don't.
Don't Strip Your Own Evidence
This is the part most guides miss entirely.
Your photos carry EXIF metadata — date, time, camera, and frequently GPS coordinates. That data quietly corroborates when and where the damage was recorded, which is exactly the kind of thing that matters if a claim is ever questioned.
Several common habits destroy it:
- Screenshotting a photo instead of sending the file. You lose the metadata and a lot of image quality.
- Sending through some messaging apps, which recompress images and strip metadata by default.
- Re-saving through an editor to shrink the file.
Send the original files wherever you can. It's the single easiest way to keep your documentation as strong as it was when you took it.
Use the Portal If You Can
Where your insurer provides a claim portal or app, that is the right first choice — not because it's the most convenient, but because anything uploaded there is attached to your claim file automatically. No reliance on an adjuster forwarding an email, and a record that it was submitted.
Practical tips: upload on Wi-Fi rather than cellular, send in small batches rather than one large push, and keep going until you get a confirmation screen. If uploads keep failing, photograph or screenshot the error before you call — it speeds up the support conversation considerably.
Getting Video Down to a Sendable Size
Video is where size problems actually bite, and the fix usually costs you nothing evidentially.
Record at 1080p, not 4K. On iPhone: Settings → Camera → Record Video. On most Android phones it's in the camera app's own settings. Dropping from 4K to 1080p cuts the file to roughly a quarter of the size, and 1080p is more than enough to show a cracked window or a water-stained ceiling. If you've already shot in 4K, keep the original and send a re-exported copy.
Shoot shorter clips. Several focused thirty-second clips are easier to upload, and easier for an adjuster to review, than one eight-minute walkthrough.
Don't over-compress. There's a real tension here. Compress a photo hard enough and the hairline crack you're claiming for stops being visible — you've damaged your own evidence to fit an arbitrary upload limit. If the choice is between heavy compression and finding another delivery method, find another delivery method.
When the Portal Won't Take It
If uploads keep failing or the portal clearly can't handle the volume, ask your adjuster how they'd like to receive it. Most are entirely used to this and will tell you what works. Many will accept a download link by email.
That's the practical role for a transfer tool: the email itself stays tiny, so no attachment limit applies on either end, and the full-quality originals travel intact with their metadata.
Sending the originals
Realtime Sender handles up to 30GB free with no account, so a complete set of original photos and video goes in one transfer. You get a short code to include in your email or give over the phone.
Two things to be straight about. Transfers are protected in transit and delete automatically after download or when the code expires — good for privacy, but it means you must keep your own copies, and the adjuster needs to collect it reasonably promptly. And this is a general-purpose transfer tool, not a regulated claims system: if your insurer offers a secure upload channel, that is the better route for anything containing personal details.
Whatever method you use, keep every original on your own device and a backup. Never let the only copy of your documentation exist inside a transfer, an email, or a portal upload.
A Word on Privacy
Claim files tend to accumulate personal information — your address, policy number, sometimes medical or financial detail depending on the claim type. A few sensible habits:
- Prefer the insurer's portal for anything containing personal details. It exists for this and creates an audit trail.
- Keep policy numbers and personal data out of email message bodies where you reasonably can.
- Be wary of anyone contacting you unprompted after a loss and asking you to upload documents to an unfamiliar site. Post-disaster claim fraud is a real pattern in the US. Verify through the number on your policy or your insurer's official app.
- If a contractor or public adjuster asks for your full documentation set, that can be perfectly legitimate — but confirm who they are first.
For the general principles behind choosing a transfer method for sensitive material, see our guide to secure file sharing for teams and businesses.
Frequently Asked Questions
Why won't my damage photos upload to the claim portal?
Usually one of three reasons. The portal has a per-file or per-session size cap and your phone photos exceed it. The portal limits how many files you can attach at once. Or the upload is timing out on a slow connection before it finishes. Phone photos are commonly 3 to 5MB each and 4K video runs around 350MB per minute, so twenty photos and a short walkthrough clip can easily exceed a portal's allowance.
Should I compress photos before sending them to my insurer?
Be careful. Heavy compression can blur exactly the detail you are trying to evidence, such as a hairline crack or a serial number. Prefer sending the originals through a method that can carry them. If you must reduce size, resize moderately rather than applying aggressive quality compression, and never compress the only copy you have.
How do I send a video to my insurance adjuster?
Try the claim portal first, since anything uploaded there is attached to your claim file automatically. If the video is too large, ask your adjuster how they prefer to receive it. Most will accept a download link by email. Record at 1080p rather than 4K where possible, which cuts the file to roughly a quarter of the size while remaining clear enough to show damage.
Does metadata in my photos matter for a claim?
It can help. Photos normally carry the date, time and often GPS location in their EXIF metadata, which supports when and where damage was recorded. Screenshotting a photo or passing it through some messaging apps strips that metadata. Sending original files preserves it, which is a reason to avoid re-saving images before you send them.
Is it safe to email insurance claim documents?
Standard email is not encrypted end to end and claim documents often contain personal information, so prefer your insurer's own portal where one exists, since it is built for the purpose and creates a record. If you must send outside the portal, avoid putting policy numbers and personal details in the message body, and ask your adjuster whether they offer a secure upload option.
How many photos should I send for a claim?
More than feels necessary. Capture wide shots establishing the whole room or property, mid-range shots showing each damaged area in context, and close-ups of specific damage. Include undamaged areas for comparison, and photograph model and serial plates on any appliance or equipment being claimed. You cannot go back and re-photograph damage after a repair.
General information only, not insurance or legal advice. Claim requirements, accepted submission methods and upload limits vary by insurer and by policy — follow the instructions your own insurer and adjuster give you.