Top Problems with Exterior Painting
Are you staring at your home’s freshly painted siding thinking… “Why does it still look off?” Or worse—did you hire a painter and now see drips, missed spots, or blotchy trim work?
Look, exterior painting is no joke. When it’s done right, it protects your home, boosts curb appeal, and can last 7–10 years or more. But when it’s rushed or done by someone who’s just “spraying and praying”—you end up paying to fix it later.
We recently did a walkthrough on a house in Crystal Lake (yep, even one of our own crews!), pointing out the little things that can go wrong—and what to do about them. Here’s what to watch for:
❌ Missed Caulking on Exterior Siding
If siding seams or trim joints weren’t re-caulked before painting, moisture can creep in—leading to rot, mildew, and cracked paint. On this project, a few seams were totally missed.
Solution:
- Re-caulk with a high-quality exterior-grade sealant (we use SherMax or Big Stretch)
- Allow dry time before repainting

Homeowner Tip: Run your hand along seams. If you feel a gap—it probably wasn’t caulked right.
❌ Paint Not Applied Behind Gutters
You’d be shocked how many painters skip behind downspouts and gutters. This probably ranks number 1 with Top Problems with Exterior Painting. On this job? ome of the gutters were taken down but were never even removed or pulled away.
Why it matters: That exposed raw wood is going to peel or rot. You won’t notice it for a year—but when it shows up, it’s costly.

Fix:
- Temporarily detach downspouts
- Back-roll or brush behind them
❌ Overspray on Windows and Fixtures
Sprayers are great for speed, but when they’re not masked off? You get cloudy windows, speckled light fixtures, and paint dust everywhere.
Fix:
- Use painter’s plastic and masking tape before spraying
- Overspray removal with razor blades or mineral spirits (if safe for the surface)

❌ Drips and Uneven Paint Application
We saw several spots with visible drips—usually a sign of too much paint applied too fast or poor prep.
Fix:
- Sand drips smooth
- Touch-up or recoat the area with proper technique
Pro Tip: Paint in cooler weather (under 85°F) and avoid direct sun to prevent fast drying and sagging.
❌ Only One Coat Around Trim and Windows
It looks fine from 10 feet away… but get close, and you’ll see the trim edges bleeding through because they only got one coat.
Fix:
- Apply a second full coat around all edges, windows, and trim boards
Why we care: These are the details that make a house look finished versus flipped.
❌ Boards Missed Entirely During Painting
Yep, we found whole boards that were skipped. Usually it’s the bottom edge or behind landscape areas.
Fix:
- Walk the home before calling a job “done”
- Use a checklist for touch-ups (we’ve got one—we’ll share it if you want!)
🔍 FAQs: Common Questions About Exterior Paint Problems
What are the most common problems with exterior paint jobs?
Drips, missed areas, peeling, fading, poor prep, and improper caulking. Most issues come from rushing or skipping steps. Read more about peeling paint here !
Should gutters be removed before painting?
Not always removed—but they should be pulled away or masked off to allow access behind them.
Can I paint over paint drips?
You’ll need to sand them first. Painting over a drip only makes a bigger, uglier drip.
How do I know if only one coat was applied?
Edges and trim will show through. Look closely around window frames or where colors meet.
Can a bad exterior paint job be fixed?
Yes! But it depends on the issue. Sometimes touch-ups are enough. Other times, whole sides need to be redone.
📊 DIY vs Pro Paint Comparison Chart
| Issue | DIY or Cheap Labor | D’Franco Pro Team |
|---|---|---|
| Missed Caulking | ✅ Common | 🚫 Fixed in prep |
| Paint Drips | ✅ Often Happens | 🚫 Re-coated |
| Overspray | ✅ Unmasked Windows | 🚫 Taped/Masked |
| One-Coat Coverage | ✅ Budget Painters | ✅ Two-Coat Min. |
| Behind Gutters Missed | ✅ Rarely Touched | ✅ Always Addressed |
🎯 Don’t Settle for Sloppy Paint Jobs
These problems aren’t just cosmetic—they affect your siding’s lifespan and your home’s value. We’re committed to getting it right. That’s why we:
- Vet and background check every worker
- Offer free touch-ups within 1 year
- Provide free color consultations
And if you’ve had a bad experience before? We get it—and we’ll make it right.
💸 Don’t forget our “Give $200, Get $200” Referral Program
📺 And subscribe to our YouTube Channel for more walk-throughs, behind-the-scenes looks, and paint problem-solving tips.
Need mor einformation about top exteripr paint and stain?
Need help fixing your exterior paint mess? Or just want it done right the first time?
👉 Let’s talk. We serve Huntley, Elgin, Crystal Lake, Bartlett, Pingree Grove, and surrounding communities.